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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (7)transporters (2) Show 9 proteins XML

enzymes (7)transporters (2) Show 9 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014613

Secondary Accession Numbers

HMDB0041865
HMDB14613
HMDB41865

Metabolite Identification

Common Name

Tetrahydrocannabinol

Description

Tetrahydrocannabinol, abbreviated THC, is a cannabinoid identified in cannabis and is its principal psychoactive constituent. First isolated in 1964, in its pure form, it is a glassy solid when cold, and becomes viscous and sticky if warmed. Synthetically prepared THC, officially referred to by its INN, dronabinol, is available by prescription in the U.S. and Canada under the brand name Marinol. The mechanism of action of THC is not completely understood. It is thought that cannabinoid receptors in neural tissues may mediate the effects of cannabinoids. Animal studies suggest that Marinol's antiemetic effects may be due to inhibition of the vomiting control mechanism in the medulla oblongata. A literature review on the subject concluded that "Cannabis use appears to be neither a sufficient nor a necessary cause for psychosis. It is a component cause, part of a complex constellation of factors leading to psychosis." Likewise, a French review from 2009 came to a conclusion that cannabis use, particularly that before age 15, was a factor in the development of schizophrenic disorders. An aromatic terpenoid, THC has a very low solubility in water, but good solubility in most organic solvents, specifically lipids and alcohols. The presence of these specialized cannabinoid receptors in the brain led researchers to the discovery of endocannabinoids, such as anandamide and 2-arachidonoyl glyceride (2-AG). THC targets receptors in a manner far less selective than endocannabinoid molecules released during retrograde signalling, as the drug has a relatively low cannabinoid receptor efficacy and affinity. In populations of low cannabinoid receptor density, THC may act to antagonize endogenous agonists that possess greater receptor efficacy. THC is a lipophilic molecule and may bind non-specifically to a variety of receptors in the brain and body, such as adipose tissue. Dronabinol is only found in individuals that have used or taken this drug. It is extracted from the resin of Cannabis sativa (marijuana, hashish). The isomer delta-9-tetrahydrocannabinol is considered the most active form, producing the characteristic mood and perceptual changes associated with this compound. In the United States, Marinol has been rescheduled from Schedule II to Schedule III of the Controlled Substances Act in 1999, reflecting a finding that THC had a potential for abuse less than that of cocaine and heroin. As a Schedule III drug, it is available by prescription and is considered to be non-narcotic and to have a low risk of physical or mental dependence. Marinol has been approved by the U.S. Food and Drug Administration (FDA) in the treatment of anorexia in AIDS patients, as well as for refractory nausea and vomiting of patients undergoing chemotherapy, which has raised much controversy as to why natural THC is still a Schedule I drug. Efforts to get cannabis rescheduled as analogous to Marinol have not succeeded thus far. In April 2005, Canadian authorities approved the marketing of Sativex, a mouth spray for multiple sclerosis patients, who can use it to alleviate neuropathic pain and spasticity. Sativex contains tetrahydrocannabinol together with cannabidiol and is a preparation of whole cannabis rather than individual cannabinoids. It is marketed in Canada by GW Pharmaceuticals, being the first cannabis-based prescription drug in the world (in modern times). In addition, Sativex received European regulatory approval in 2010. An analog of dronabinol, nabilone, is available commercially in Canada under the trade name Cesamet, manufactured by Valeant Pharmaceuticals. Cesamet has also received FDA approval and began marketing in the U.S. in 2006. It is a Schedule II drug.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014613
     RDKit          3D
Tetrahydrocannabinol
 53 55  0  0  0  0  0  0  0  0999 V2000
    6.7328   -0.9095   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3359   -1.2149   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853   -0.6812   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3896    0.8183    0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3204    1.2928    0.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9623    0.9905    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2192    1.8454   -0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784    1.4917   -0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7700    2.3972   -1.4693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6049    0.2972   -0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1279   -0.5816    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856   -0.2104    0.8777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4857   -1.7934    0.8632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8802   -1.8426    1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4539   -3.0408    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040   -1.9613    2.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5753   -0.5866    0.6796 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0555   -0.6944    0.6798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7488    0.4525    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0172    0.9664   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8199    1.8902   -2.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7706    0.6815   -1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9542   -0.2007   -0.6450 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4755   -1.3115   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9243   -1.4122    0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9005    0.1770   -0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2006   -2.3171   -1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4904    0.7667    1.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6234    2.8020   -0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853    3.2611   -1.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9707   -0.8978    1.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739   -3.8397    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9544   -3.0320    2.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    0.2170    1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -1.6247    0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7786    0.1903   -0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370    1.2810    0.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3840    1.9265   -3.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8580    1.4996   -2.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8624    2.8757   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652    1.1126   -2.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7984   -1.2088   -1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 23 17  1  0
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  1 24  1  0
  1 25  1  0
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  2 27  1  0
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  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
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 17 44  1  1
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 21 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  6
M  END


  Mrv1652309272007302D          

 25 27  0  0  0  0            999 V2000
 9998.201810001.7607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.064010001.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.778610001.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.493110001.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.211710001.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.926310001.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.053610000.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.199710000.9347    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9997.485010000.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.770510000.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7705 9999.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4850 9998.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.201210000.1089    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.345910001.3483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.631410001.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.916910001.3482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.916810000.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.631310000.1107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.345910000.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2058 9998.5522    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6334 9999.2650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2048 9999.2650    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.4353 9998.2089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3928 9998.2189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9192 9998.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10  7  1  0  0  0  0
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 13  8  1  6  0  0  0
 14 15  2  0  0  0  0
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 14  2  1  0  0  0  0
  1 16  1  0  0  0  0
 17 13  1  0  0  0  0
 22 20  1  1  0  0  0
 25 23  1  0  0  0  0
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 21 25  1  0  0  0  0
 13 22  1  0  0  0  0
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 21 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014613

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C=C(C)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1

> <INCHI_KEY>
CYQFCXCEBYINGO-IAGOWNOFSA-N

> <FORMULA>
C21H30O2

> <MOLECULAR_WEIGHT>
314.4617

> <EXACT_MASS>
314.224580204

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
38.95694121819908

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol

> <ALOGPS_LOGP>
7.29

> <JCHEM_LOGP>
5.944157107333333

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.342429150192967

> <JCHEM_PKA_STRONGEST_BASIC>
-4.893304388168227

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
96.73350000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
THC

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014613
     RDKit          3D
Tetrahydrocannabinol
 53 55  0  0  0  0  0  0  0  0999 V2000
    6.7328   -0.9095   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3359   -1.2149   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853   -0.6812   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3896    0.8183    0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3204    1.2928    0.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9623    0.9905    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2192    1.8454   -0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784    1.4917   -0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7700    2.3972   -1.4693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6049    0.2972   -0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1279   -0.5816    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856   -0.2104    0.8777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4857   -1.7934    0.8632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8802   -1.8426    1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4539   -3.0408    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040   -1.9613    2.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5753   -0.5866    0.6796 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0555   -0.6944    0.6798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7488    0.4525    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0172    0.9664   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8199    1.8902   -2.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7706    0.6815   -1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9542   -0.2007   -0.6450 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4755   -1.3115   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2006   -2.3171   -1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4056   -1.2123    0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2909   -0.9351   -0.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3477    1.2759   -0.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3716    1.0789    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4287    2.3760    1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904    0.7667    1.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6234    2.8020   -0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853    3.2611   -1.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9707   -0.8978    1.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739   -3.8397    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8643   -2.8292   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3005   -3.4878    1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9506   -1.5341    3.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1730   -1.3880    3.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9544   -3.0320    2.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    0.2170    1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -1.6247    0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3980   -0.8022    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7786    0.1903   -0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370    1.2810    0.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3840    1.9265   -3.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8580    1.4996   -2.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8624    2.8757   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652    1.1126   -2.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7984   -1.2088   -1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 12  6  1  0
 23 17  1  0
 23 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  1
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  6
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8663.3108669.953   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8668.6538669.953   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8669.9878669.186   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8671.3208669.953   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8672.6628669.186   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8673.9968669.953   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8659.3008667.644   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0    8663.3068668.411   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0    8661.9728667.640   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8660.6388666.870   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8660.6388665.330   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.9728664.560   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.3098666.870   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.3128669.183   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.9798669.953   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.6458669.183   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.6458667.643   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8665.9788666.873   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8667.3128667.643   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0    8663.3178663.964   0.000  0.00  0.00           H+0
HETATM   21  O   UNK     0    8665.9828665.295   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0    8663.3168665.295   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8665.6138663.323   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8663.6678663.342   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8664.6498664.525   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2    3   14                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7   10                                                            
CONECT    8   13                                                            
CONECT    9   10   13                                                       
CONECT   10    9   11    7                                                  
CONECT   11   10   12                                                       
CONECT   12   11   22                                                       
CONECT   13    9    8   17   22                                             
CONECT   14   15   19    2                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17    1                                                  
CONECT   17   16   18   13                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   14                                                       
CONECT   20   22                                                            
CONECT   21   25   18                                                       
CONECT   22   20   25   13   12                                             
CONECT   23   25                                                            
CONECT   24   25                                                            
CONECT   25   23   24   22   21                                             
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0014613
HETATM    1  C1  UNL     1       6.733  -0.909  -0.588  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.336  -1.215  -1.090  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.285  -0.681  -0.146  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.390   0.818   0.015  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.320   1.293   0.964  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.962   0.990   0.508  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.219   1.845  -0.279  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.078   1.492  -0.681  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.770   2.397  -1.469  1.00  0.00           O  
HETATM   10  C9  UNL     1      -0.605   0.297  -0.293  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.128  -0.582   0.502  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.386  -0.210   0.878  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.486  -1.793   0.863  1.00  0.00           O  
HETATM   14  C12 UNL     1      -1.880  -1.843   1.151  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.454  -3.041   0.452  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.004  -1.961   2.659  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.575  -0.587   0.680  1.00  0.00           C  
HETATM   18  C16 UNL     1      -4.056  -0.694   0.680  1.00  0.00           C  
HETATM   19  C17 UNL     1      -4.749   0.452   0.007  1.00  0.00           C  
HETATM   20  C18 UNL     1      -4.017   0.966  -1.169  1.00  0.00           C  
HETATM   21  C19 UNL     1      -4.820   1.890  -2.061  1.00  0.00           C  
HETATM   22  C20 UNL     1      -2.771   0.681  -1.471  1.00  0.00           C  
HETATM   23  C21 UNL     1      -1.954  -0.201  -0.645  1.00  0.00           C  
HETATM   24  H1  UNL     1       7.475  -1.312  -1.299  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.924  -1.412   0.382  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.901   0.177  -0.528  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.201  -2.317  -1.125  1.00  0.00           H  
HETATM   28  H5  UNL     1       5.223  -0.850  -2.118  1.00  0.00           H  
HETATM   29  H6  UNL     1       4.406  -1.212   0.823  1.00  0.00           H  
HETATM   30  H7  UNL     1       3.291  -0.935  -0.542  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.348   1.276  -0.970  1.00  0.00           H  
HETATM   32  H9  UNL     1       5.372   1.079   0.478  1.00  0.00           H  
HETATM   33  H10 UNL     1       3.429   2.376   1.193  1.00  0.00           H  
HETATM   34  H11 UNL     1       3.490   0.767   1.928  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.623   2.802  -0.598  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.385   3.261  -1.749  1.00  0.00           H  
HETATM   37  H14 UNL     1       1.971  -0.898   1.505  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.674  -3.840   0.284  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.864  -2.829  -0.556  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.300  -3.488   1.043  1.00  0.00           H  
HETATM   41  H18 UNL     1      -2.951  -1.534   3.035  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.173  -1.388   3.100  1.00  0.00           H  
HETATM   43  H20 UNL     1      -1.954  -3.032   2.901  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.262   0.217   1.412  1.00  0.00           H  
HETATM   45  H22 UNL     1      -4.348  -1.625   0.151  1.00  0.00           H  
HETATM   46  H23 UNL     1      -4.398  -0.802   1.729  1.00  0.00           H  
HETATM   47  H24 UNL     1      -5.779   0.190  -0.305  1.00  0.00           H  
HETATM   48  H25 UNL     1      -4.837   1.281   0.740  1.00  0.00           H  
HETATM   49  H26 UNL     1      -4.384   1.927  -3.077  1.00  0.00           H  
HETATM   50  H27 UNL     1      -5.858   1.500  -2.188  1.00  0.00           H  
HETATM   51  H28 UNL     1      -4.862   2.876  -1.572  1.00  0.00           H  
HETATM   52  H29 UNL     1      -2.365   1.113  -2.372  1.00  0.00           H  
HETATM   53  H30 UNL     1      -1.798  -1.209  -1.171  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7    7   12
CONECT    7    8   35
CONECT    8    9   10   10
CONECT    9   36
CONECT   10   11   23
CONECT   11   12   12   13
CONECT   12   37
CONECT   13   14
CONECT   14   15   16   17
CONECT   15   38   39   40
CONECT   16   41   42   43
CONECT   17   18   23   44
CONECT   18   19   45   46
CONECT   19   20   47   48
CONECT   20   21   22   22
CONECT   21   49   50   51
CONECT   22   23   52
CONECT   23   53
END

HMDB0014613
     RDKit          3D
Tetrahydrocannabinol
 53 55  0  0  0  0  0  0  0  0999 V2000
    6.7328   -0.9095   -0.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3359   -1.2149   -1.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2853   -0.6812   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3896    0.8183    0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3204    1.2928    0.9643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9623    0.9905    0.5078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2192    1.8454   -0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784    1.4917   -0.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7700    2.3972   -1.4693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6049    0.2972   -0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1279   -0.5816    0.5024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3856   -0.2104    0.8777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4857   -1.7934    0.8632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8802   -1.8426    1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4539   -3.0408    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0040   -1.9613    2.6591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5753   -0.5866    0.6796 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0555   -0.6944    0.6798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7488    0.4525    0.0070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0172    0.9664   -1.1692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8199    1.8902   -2.0614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7706    0.6815   -1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9542   -0.2007   -0.6450 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4755   -1.3115   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9243   -1.4122    0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9005    0.1770   -0.5275 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2006   -2.3171   -1.1246 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2229   -0.8498   -2.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4056   -1.2123    0.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2909   -0.9351   -0.5420 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3477    1.2759   -0.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3716    1.0789    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4287    2.3760    1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4904    0.7667    1.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6234    2.8020   -0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3853    3.2611   -1.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9707   -0.8978    1.5047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739   -3.8397    0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8643   -2.8292   -0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3005   -3.4878    1.0427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9506   -1.5341    3.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1730   -1.3880    3.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9544   -3.0320    2.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2617    0.2170    1.4116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -1.6247    0.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3980   -0.8022    1.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7786    0.1903   -0.3054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8370    1.2810    0.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3840    1.9265   -3.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8580    1.4996   -2.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8624    2.8757   -1.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3652    1.1126   -2.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7984   -1.2088   -1.1714 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 12  6  1  0
 23 17  1  0
 23 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  7 35  1  0
  9 36  1  0
 12 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  1
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
 22 52  1  0
 23 53  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-delta9-trans-Tetrahydrocannabinol	ChEBI
1-trans-delta-9-Tetrahydrocannabinol	ChEBI
3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,D)pyran-1-ol	ChEBI
6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol	ChEBI
Delta(1)-Tetrahydrocannabinol	ChEBI
delta9-Tetrahydrocannabinol	ChEBI
Delta(9)-THC	ChEBI
Dronabinol	ChEBI
Dronabinolum	ChEBI
Syndros	ChEBI
THC	Kegg
Marinol	Kegg
(-)-Δ9-trans-tetrahydrocannabinol	Generator
1-trans-Δ-9-tetrahydrocannabinol	Generator
Δ(1)-tetrahydrocannabinol	Generator
Δ9-tetrahydrocannabinol	Generator
Δ(9)-THC	Generator
DELTA-9-THC	HMDB
DELTA-9-TETRAHYDROCANNABINOL	HMDB
Δ-9-THC	HMDB
Δ-9-tetrahydrocannabinol	HMDB
Tetrahydrocannabinol, (6a-trans)-isomer	HMDB
9-Ene-tetrahydrocannabinol	HMDB
Tetrahydrocannabinol, (6ar-cis)-isomer	HMDB
Tetrahydrocannabinol, (6as-cis)-isomer	HMDB
Tetrahydrocannabinol, trans isomer	HMDB
delta(9)-Tetrahydrocannabinol	HMDB
delta(1)-THC	HMDB
9 Ene tetrahydrocannabinol	HMDB
Solvay brand OF tetrahydrocannabinol	HMDB
Tetrahydrocannabinol, trans-(+-)-isomer	HMDB
Tetrahydrocannabinol, trans-isomer	HMDB
delta 1-Tetrahydrocannabinol	HMDB
(-)- delta 9-Tetrahydrocannabinol	HMDB
(-)-delta 1-Tetrahydrocannabinol	HMDB
(-)-delta 9-THC	HMDB
(-)-delta 9-trans-Tetrahydrocannabinol	HMDB
(-)-trans-delta 1-Tetrahydrocannabinol	HMDB
(-)-trans-delta 9-Tetrahydrocannabinol	HMDB
(-)-trans-delta 9-THC	HMDB
(L)-delta 1-Tetrahydrocannabinol	HMDB
1-trans-delta 9-Tetrahydrocannabinol	HMDB
14C-delta 1-Tetrahydrocannabinol	HMDB
delta 1-THC	HMDB
delta 9-Tetrahydrocannabinol	HMDB
delta 9-THC	HMDB
delta 9-trans-Tetrahydrocannabinol	HMDB
Exocyclic delta (9)(11)-tetrahydrocannabiol	HMDB
L-delta 1-trans-Tetrahydrocannabinol	HMDB
L-trans-delta 9-Tetrahydrocannabinol	HMDB
Primolut	HMDB
trans-delta (-)-9-Tetrahydrocannabinol	HMDB
trans-delta 9-Tetrahydrocannabinol	HMDB
Tetrahydrocannabinol	ChEBI
(-)-3,4-trans-delta1-Tetrahydrocannabinol	PhytoBank
(-)-3,4-trans-Δ1-Tetrahydrocannabinol	PhytoBank
(-)-delta1-Tetrahydrocannabinol	PhytoBank
(-)-delta9-THC	PhytoBank
(-)-delta9-Tetrahydrocannabinol	PhytoBank
(-)-trans-delta1-Tetrahydrocannabinol	PhytoBank
(-)-trans-delta9-THC	PhytoBank
(-)-trans-delta9-Tetrahydrocannabinol	PhytoBank
(-)-trans-Δ1-Tetrahydrocannabinol	PhytoBank
(-)-trans-Δ9-THC	PhytoBank
(-)-trans-Δ9-Tetrahydrocannabinol	PhytoBank
(-)-Δ1-Tetrahydrocannabinol	PhytoBank
(-)-Δ9-THC	PhytoBank
(-)-Δ9-Tetrahydrocannabinol	PhytoBank
(l)-delta1-Tetrahydrocannabinol	PhytoBank
(l)-Δ1-Tetrahydrocannabinol	PhytoBank
delta1-THC	PhytoBank
delta1-Tetrahydrocannabinol	PhytoBank
delta9-THC	PhytoBank
delta9-trans-Tetrahydrocannabinol	PhytoBank
l-delta1-trans-Tetrahydrocannabinol	PhytoBank
l-trans-delta9-Tetrahydrocannabinol	PhytoBank
l-trans-Δ9-Tetrahydrocannabinol	PhytoBank
l-Δ1-trans-Tetrahydrocannabinol	PhytoBank
trans-(-)-delta9-Tetrahydrocannabinol	PhytoBank
trans-(-)-Δ9-Tetrahydrocannabinol	PhytoBank
trans-delta9-Tetrahydrocannabinol	PhytoBank
trans-Δ9-Tetrahydrocannabinol	PhytoBank
Δ1-THC	PhytoBank
Δ1-Tetrahydrocannabinol	PhytoBank
Δ9-THC	PhytoBank
Δ9-trans-Tetrahydrocannabinol	PhytoBank

Chemical Formula

C₂₁H₃₀O₂

Average Molecular Weight

314.4617

Monoisotopic Molecular Weight

314.224580204

IUPAC Name

(6aR,10aR)-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol

Traditional Name

THC

CAS Registry Number

1972-08-3

SMILES

[H][C@@]12C=C(C)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21

InChI Identifier

InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3/t16-,17-/m1/s1

InChI Key

CYQFCXCEBYINGO-IAGOWNOFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyketide (CHEBI:66964 )
diterpenoid (CHEBI:66964 )
phytocannabinoid (CHEBI:66964 )
benzochromene (CHEBI:66964 )
Cannabinoids (C06972 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	200 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0026 g/L	Not Available
LogP	5.648	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0026 g/L	ALOGPS
logP	7.29	ALOGPS
logP	5.94	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	96.73 m³·mol⁻¹	ChemAxon
Polarizability	38.96 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.307	31661259
DarkChem	[M-H]-	174.669	31661259
DeepCCS	[M-2H]-	216.173	30932474
DeepCCS	[M+Na]+	191.481	30932474
AllCCS	[M+H]+	180.0	32859911
AllCCS	[M+H-H2O]+	176.9	32859911
AllCCS	[M+NH4]+	182.9	32859911
AllCCS	[M+Na]+	183.8	32859911
AllCCS	[M-H]-	188.1	32859911
AllCCS	[M+Na-2H]-	188.7	32859911
AllCCS	[M+HCOO]-	189.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.69 minutes	32390414
Predicted by Siyang on May 30, 2022	23.5116 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.3 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3121.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	752.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	297.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	402.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	540.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1212.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1110.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	98.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2096.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	748.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1988.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	776.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	557.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	508.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	619.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydrocannabinol	[H][C@@]12C=C(C)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21	3292.1	Standard polar	33892256
Tetrahydrocannabinol	[H][C@@]12C=C(C)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21	2533.1	Standard non polar	33892256
Tetrahydrocannabinol	[H][C@@]12C=C(C)CC[C@@]1([H])C(C)(C)OC1=CC(CCCCC)=CC(O)=C21	2519.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydrocannabinol,1TMS,isomer #1	CCCCCC1=CC2=C(C(O[Si](C)(C)C)=C1)[C@@H]1C=C(C)CC[C@H]1C(C)(C)O2	2328.4	Semi standard non polar	33892256
Tetrahydrocannabinol,1TBDMS,isomer #1	CCCCCC1=CC2=C(C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H]1C=C(C)CC[C@H]1C(C)(C)O2	2555.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydrocannabinol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0597-4090000000-670e40c1592b93325e44	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydrocannabinol GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-6009000000-735bce5abc1be2637810	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydrocannabinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydrocannabinol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-01pp-4792000000-06532e533cb7794b7c37	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol Orbitrap 11V, positive-QTOF	splash10-014i-0219000000-1916f155ea706f1bfd78	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol Orbitrap 15V, positive-QTOF	splash10-05mx-3943000000-9b0e61162051930e030f	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol Orbitrap 19V, positive-QTOF	splash10-052f-3920000000-06615e927292d6b78f04	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol Orbitrap 25V, positive-QTOF	splash10-006x-5900000000-c44a1196b35ae31ac75c	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol Orbitrap 31V, positive-QTOF	splash10-00xu-7900000000-d06351b5900dfe483bd6	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol Orbitrap 37V, positive-QTOF	splash10-00tf-9600000000-14d6a1649ef828de05e3	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol Orbitrap 43V, positive-QTOF	splash10-00mo-9400000000-c1c5f46aa3925b6b440f	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol Orbitrap 50V, positive-QTOF	splash10-00ou-9300000000-fec356cc420b4d525c37	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol Orbitrap 59V, positive-QTOF	splash10-016u-9200000000-295f54d67e0fa9512778	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol Orbitrap 71V, positive-QTOF	splash10-0fvl-9200000000-92620f75edee11220267	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol n/a 21V, positive-QTOF	splash10-053f-0980000000-c5e3986b120b13bf6cad	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol n/a 21V, positive-QTOF	splash10-00dr-0900000000-71e91d90ab20dda21879	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol n/a 21V, positive-QTOF	splash10-0002-9000000000-0c6530b23f4594b0199d	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol n/a 21V, positive-QTOF	splash10-03di-0910000000-13e75d88a02fafe0bbe2	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol n/a 21V, positive-QTOF	splash10-000j-0900000000-ae7ab2b9c0db456ba4d4	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol n/a 21V, positive-QTOF	splash10-00lr-0490000000-aebf4a983943679cba93	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tetrahydrocannabinol n/a 21V, positive-QTOF	splash10-004i-0910000000-13eb5c07bf46dbbbc6c3	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrocannabinol 10V, Positive-QTOF	splash10-014i-1239000000-dd0a437774bcd5f12cd9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrocannabinol 20V, Positive-QTOF	splash10-0600-6291000000-48cdeee605af2033e358	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrocannabinol 40V, Positive-QTOF	splash10-0aou-9140000000-f6fc10c62a978b5bb9b0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrocannabinol 10V, Negative-QTOF	splash10-03di-0009000000-1a8c2415357935328858	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrocannabinol 20V, Negative-QTOF	splash10-03di-0429000000-d0c2b14e825c4f547980	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrocannabinol 40V, Negative-QTOF	splash10-01re-3930000000-3f6ef979ec17030832a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrocannabinol 10V, Negative-QTOF	splash10-03di-0009000000-2514638890974c4f71f3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydrocannabinol 20V, Negative-QTOF	splash10-03di-0009000000-f9f1dddf06624032e0de	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00470	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00470	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00470

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Tetrahydrocannabinol

METLIN ID

Not Available

PubChem Compound

16078

PDB ID

Not Available

ChEBI ID

66964

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Gregg JM, Small EW, Moore R, Raft D, Toomey TC: Emotional response to intravenous delta9tetrahydrocannabinol during oral surgery. J Oral Surg. 1976 Apr;34(4):301-13. [PubMed:1062533 ]
Schuel H, Burkman LJ: A tale of two cells: endocannabinoid-signaling regulates functions of neurons and sperm. Biol Reprod. 2005 Dec;73(6):1078-86. Epub 2005 Aug 24. [PubMed:16120829 ]
Zhu W, Friedman H, Klein TW: Delta9-tetrahydrocannabinol induces apoptosis in macrophages and lymphocytes: involvement of Bcl-2 and caspase-1. J Pharmacol Exp Ther. 1998 Aug;286(2):1103-9. [PubMed:9694974 ]
Zangen A, Solinas M, Ikemoto S, Goldberg SR, Wise RA: Two brain sites for cannabinoid reward. J Neurosci. 2006 May 3;26(18):4901-7. [PubMed:16672664 ]
Consroe P, Martin P, Eisenstein D: Anticonvulsant drug antagonism of delta9tetrahydrocannabinol-induced seizures in rabbits. Res Commun Chem Pathol Pharmacol. 1977 Jan;16(1):1-13. [PubMed:841172 ]
Concheiro M, de Castro A, Quintela O, Cruz A, Lopez-Rivadulla M: Development and validation of a method for the quantitation of Delta9tetrahydrocannabinol in oral fluid by liquid chromatography electrospray-mass-spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Oct 25;810(2):319-24. [PubMed:15380731 ]

Enzymes

Enzyme Details

1. Prostaglandin G/H synthase 1

General function:: Involved in peroxidase activity
Specific function:: May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:: PTGS1
Uniprot ID:: P23219
Molecular weight:: 68685.82

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]

Enzyme Details

3. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

4. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

5. Cytochrome P450 1A1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP1A1
Uniprot ID:: P04798
Molecular weight:: 58164.815

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

6. Cytochrome P450 2A6

General function:: Involved in monooxygenase activity
Specific function:: Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:: CYP2A6
Uniprot ID:: P11509
Molecular weight:: 56517.005

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

7. Cannabinoid receptor 1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Involved in cannabinoid-induced CNS effects. Acts by inhibiting adenylate cyclase. Could be a receptor for anandamide. Inhibits L-type Ca(2+) channel current. Isoform 2 and isoform 3 have altered ligand binding
Gene Name:: CNR1
Uniprot ID:: P21554
Molecular weight:: 52857.4

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Pryce G, Giovannoni G, Baker D: Mifepristone or inhibition of 11beta-hydroxylase activity potentiates the sedating effects of the cannabinoid receptor-1 agonist Delta(9)-tetrahydrocannabinol in mice. Neurosci Lett. 2003 May 1;341(2):164-6. [PubMed:12686391 ]
Tsai SJ, Wang YC, Hong CJ: Association study of a cannabinoid receptor gene (CNR1) polymorphism and schizophrenia. Psychiatr Genet. 2000 Sep;10(3):149-51. [PubMed:11204352 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Tournier N, Chevillard L, Megarbane B, Pirnay S, Scherrmann JM, Decleves X: Interaction of drugs of abuse and maintenance treatments with human P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2). Int J Neuropsychopharmacol. 2010 Aug;13(7):905-15. doi: 10.1017/S1461145709990848. Epub 2009 Nov 4. [PubMed:19887017 ]

Enzyme Details

2. ATP-binding cassette sub-family G member 2

General function:: Involved in ATP binding
Specific function:: Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:: ABCG2
Uniprot ID:: Q9UNQ0
Molecular weight:: 72313.5

References

Tournier N, Chevillard L, Megarbane B, Pirnay S, Scherrmann JM, Decleves X: Interaction of drugs of abuse and maintenance treatments with human P-glycoprotein (ABCB1) and breast cancer resistance protein (ABCG2). Int J Neuropsychopharmacol. 2010 Aug;13(7):905-15. doi: 10.1017/S1461145709990848. Epub 2009 Nov 4. [PubMed:19887017 ]

Showing metabocard for Tetrahydrocannabinol (HMDB0014613)

MOL for HMDB0014613 (Tetrahydrocannabinol)

3D MOL for HMDB0014613 (Tetrahydrocannabinol)

3D SDF for HMDB0014613 (Tetrahydrocannabinol)

3D-SDF for HMDB0014613 (Tetrahydrocannabinol)

PDB for HMDB0014613 (Tetrahydrocannabinol)

3D PDB for HMDB0014613 (Tetrahydrocannabinol)

SMILES for HMDB0014613 (Tetrahydrocannabinol)

INCHI for HMDB0014613 (Tetrahydrocannabinol)

Structure for HMDB0014613 (Tetrahydrocannabinol)

3D Structure for HMDB0014613 (Tetrahydrocannabinol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

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Transporters

References

References