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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-07-25 00:07:32 UTC

Update Date

2021-09-14 15:40:56 UTC

HMDB ID

HMDB0012798

Secondary Accession Numbers

HMDB12798

Metabolite Identification

Common Name

5'-Carboxy-alpha-chromanol

Description

5'-carboxy-alpha-tocopherol is a dehydrogenation carboxylate product of 5'-hydroxy-a-tocopherol by an unidentified microsomal enzyme(s) probably via an aldehyde intermediate. The tocopherols ( a-tocopherol , b-tocopherol ,r-tocopherol and d-tocopherol ) and their corresponding tocotrienols are synthesized by plants and have vitamin E antixoidant activity (see pathway vitamin E biosynthesis ). They differ in the number and location of methyl groups on the chromanol ring. The naturally occurring form of a-tocopherol is (2R,4'R,8'R)-a-tocopherol (synonym (R,R,R)-a-tocopherol). Synthetic a-tocopherols are a racemic mixture of eight different R and S stereoisomers. Only the 2R forms are recognized as meeting human requirements. The in vivo function of vitamin E is to scavenge peroxyl radicals via its phenolic (chromanol) hydroxyl group, thus protecting lipids against free radical-catalyzed peroxidation. The tocopheryl radical formed can then be reduced by reductants such as L-ascorbate. Other major products of a-tocopherol oxidation include α-tocopherylquinone and epoxy-a-tocopherols. The metabolites a-tocopheronic acid and its lactone, known as the Simon metabolites, are generally believed to be artefacts. In addition to these oxidation products, the other major class of tocopherol metabolites is the carboxyethyl-hydroxychromans.These metabolites are produced in significant amounts in response to excess vitamin E ingestion. Vitamin E is fat-soluble and its utilization requires intestinal fat absorption mechanisms. It is secreted from the intestine into the lymphatic system in chylomicrons which subsequently enter the plasma. Lipolysis of these chylomicrons can result in delivery of vitamin E to tissues, transfer to high-density lipoproteins (and subsequently to other lipoproteins via the phospholipid exchange protein), or retention in chylomicron remnants. These remnants are taken up by the liver. Natural (R,R,R)-α-tocopherol and synthetic 2R-α-tocopherols are then preferentially secreted from the liver into plasma as a result of the specificity of the α-tocopherol transfer protein. This protein, along with the metabolism of excess vitamin E in the liver and excretion into urine and bile, mediate the supply of a-tocopherol in plasma and tissues.

Structure

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

HMDB0012798
     RDKit          3D
5'-Carboxy-alpha-chromanol
 51 52  0  0  0  0  0  0  0  0999 V2000
   -4.1410   -2.4570   -1.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4913   -1.2448   -0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535   -1.0755   -0.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2729   -2.0810   -1.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6053    0.0878   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934    1.0499    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7248    0.8740    0.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5025    1.9475    1.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3039   -0.2904   -0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6448   -0.5164    0.0497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6770    2.2451    0.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4784    1.7592    1.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    1.0786    0.5458 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2159    2.1951   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2362    0.0896    1.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2319   -0.7895    0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -0.0575    0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3436   -1.1044   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8066   -1.9287    0.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4425   -0.3718   -1.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6310   -0.4857   -0.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1389    0.4616   -2.1447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2654    0.3915   -0.4273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8087   -2.1859   -2.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7797   -2.9390   -0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4183   -3.2129   -1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5732   -2.2358   -2.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2321   -1.7060   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116   -3.0637   -0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1678    2.9247    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5753    1.8683    0.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800    1.9565    2.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3085    0.0872    0.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4077    2.9006   -0.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3234    2.8832    1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880    1.0122    2.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0630    2.6100    1.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5910    3.1413    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688    2.4776    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855    2.1323   -1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7517    0.6196    2.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967   -0.5664    1.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078   -1.3831    1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8256   -1.6054    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847    0.5312    0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0903    0.6435   -0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906   -1.6766   -1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7512   -1.3163    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8249   -2.3415    0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1068   -2.7741    0.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2983    1.4412   -2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 13 23  1  0
  9  2  1  0
 23  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 22 51  1  0
M  END


  Mrv1652303102016462D          

 23 24  0  0  1  0            999 V2000
   11.5055  -11.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6805  -11.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2681  -12.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6805  -13.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2681  -13.9179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6805  -14.6324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8555  -14.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6805  -15.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3950  -15.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1096  -15.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8242  -15.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8242  -16.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5381  -15.4574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2527  -15.8699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5381  -14.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2527  -14.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8242  -14.2199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8242  -13.3950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1096  -14.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3950  -14.2199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2681  -11.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6805  -10.3457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4431  -11.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 21  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
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  6 20  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 19  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012798

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O4/c1-11(18(21)22)7-6-9-19(5)10-8-15-14(4)16(20)12(2)13(3)17(15)23-19/h11,20H,6-10H2,1-5H3,(H,21,22)/t11?,19-/m1/s1

> <INCHI_KEY>
QWPNLVBAEZJBMI-IMFVZPHKSA-N

> <FORMULA>
C19H28O4

> <MOLECULAR_WEIGHT>
320.4232

> <EXACT_MASS>
320.198759384

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.96262790886203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2-methylpentanoic acid

> <ALOGPS_LOGP>
4.16

> <JCHEM_LOGP>
5.312855164333332

> <ALOGPS_LOGS>
-3.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.802178268699103

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.295285814500001

> <JCHEM_PKA_STRONGEST_BASIC>
-4.852614909520738

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
91.16019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012798
     RDKit          3D
5'-Carboxy-alpha-chromanol
 51 52  0  0  0  0  0  0  0  0999 V2000
   -4.1410   -2.4570   -1.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4913   -1.2448   -0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535   -1.0755   -0.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2729   -2.0810   -1.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6053    0.0878   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934    1.0499    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7248    0.8740    0.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5025    1.9475    1.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3039   -0.2904   -0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6448   -0.5164    0.0497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6770    2.2451    0.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4784    1.7592    1.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    1.0786    0.5458 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2159    2.1951   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2362    0.0896    1.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2319   -0.7895    0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -0.0575    0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3436   -1.1044   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8066   -1.9287    0.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4425   -0.3718   -1.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6310   -0.4857   -0.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1389    0.4616   -2.1447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2654    0.3915   -0.4273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8087   -2.1859   -2.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7797   -2.9390   -0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4183   -3.2129   -1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5732   -2.2358   -2.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2321   -1.7060   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116   -3.0637   -0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1678    2.9247    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5753    1.8683    0.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800    1.9565    2.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3085    0.0872    0.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4077    2.9006   -0.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3234    2.8832    1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880    1.0122    2.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0630    2.6100    1.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5910    3.1413    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688    2.4776    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855    2.1323   -1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7517    0.6196    2.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967   -0.5664    1.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078   -1.3831    1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8256   -1.6054    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847    0.5312    0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0903    0.6435   -0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906   -1.6766   -1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7512   -1.3163    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8249   -2.3415    0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1068   -2.7741    0.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2983    1.4412   -2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 13 23  1  0
  9  2  1  0
 23  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 22 51  1  0
M  END

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      21.477 -21.980   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.937 -21.980   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.167 -23.314   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.937 -24.646   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.167 -25.980   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.937 -27.314   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.397 -27.314   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.937 -28.854   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.271 -29.624   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.605 -28.854   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.939 -29.624   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.939 -31.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.271 -28.854   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      26.605 -29.624   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      25.271 -27.314   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.605 -26.544   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.939 -26.544   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.939 -25.004   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.605 -27.314   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      21.271 -26.544   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      19.167 -20.646   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      19.937 -19.312   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      17.627 -20.646   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   20                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   10   17   20                                                  
CONECT   20    6   19                                                       
CONECT   21    2   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0012798
HETATM    1  C1  UNL     1      -4.141  -2.457  -1.205  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.491  -1.245  -0.699  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.153  -1.076  -0.846  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.273  -2.081  -1.514  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.605   0.088  -0.347  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.393   1.050   0.282  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.725   0.874   0.424  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.503   1.947   1.099  1.00  0.00           C  
HETATM    9  C9  UNL     1      -4.304  -0.290  -0.070  1.00  0.00           C  
HETATM   10  O1  UNL     1      -5.645  -0.516   0.050  1.00  0.00           O  
HETATM   11  C10 UNL     1      -1.677   2.245   0.783  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.478   1.759   1.547  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.481   1.079   0.546  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.216   2.195  -0.091  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.236   0.090   1.340  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.232  -0.789   0.744  1.00  0.00           C  
HETATM   17  C16 UNL     1       3.364  -0.058   0.112  1.00  0.00           C  
HETATM   18  C17 UNL     1       4.344  -1.104  -0.430  1.00  0.00           C  
HETATM   19  C18 UNL     1       4.807  -1.929   0.726  1.00  0.00           C  
HETATM   20  C19 UNL     1       5.443  -0.372  -1.083  1.00  0.00           C  
HETATM   21  O2  UNL     1       6.631  -0.486  -0.703  1.00  0.00           O  
HETATM   22  O3  UNL     1       5.139   0.462  -2.145  1.00  0.00           O  
HETATM   23  O4  UNL     1      -0.265   0.392  -0.427  1.00  0.00           O  
HETATM   24  H1  UNL     1      -4.809  -2.186  -2.048  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.780  -2.939  -0.418  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.418  -3.213  -1.539  1.00  0.00           H  
HETATM   27  H4  UNL     1      -1.573  -2.236  -2.569  1.00  0.00           H  
HETATM   28  H5  UNL     1      -0.232  -1.706  -1.527  1.00  0.00           H  
HETATM   29  H6  UNL     1      -1.312  -3.064  -0.997  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.168   2.925   0.654  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.575   1.868   0.872  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.280   1.957   2.185  1.00  0.00           H  
HETATM   33  H10 UNL     1      -6.308   0.087   0.479  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.408   2.901  -0.059  1.00  0.00           H  
HETATM   35  H12 UNL     1      -2.323   2.883   1.446  1.00  0.00           H  
HETATM   36  H13 UNL     1      -0.788   1.012   2.291  1.00  0.00           H  
HETATM   37  H14 UNL     1       0.063   2.610   1.996  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.591   3.141   0.013  1.00  0.00           H  
HETATM   39  H16 UNL     1       2.169   2.478   0.397  1.00  0.00           H  
HETATM   40  H17 UNL     1       1.386   2.132  -1.177  1.00  0.00           H  
HETATM   41  H18 UNL     1       1.752   0.620   2.210  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.497  -0.566   1.907  1.00  0.00           H  
HETATM   43  H20 UNL     1       2.708  -1.383   1.593  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.826  -1.605   0.095  1.00  0.00           H  
HETATM   45  H22 UNL     1       3.885   0.531   0.890  1.00  0.00           H  
HETATM   46  H23 UNL     1       3.090   0.643  -0.699  1.00  0.00           H  
HETATM   47  H24 UNL     1       3.791  -1.677  -1.199  1.00  0.00           H  
HETATM   48  H25 UNL     1       4.751  -1.316   1.663  1.00  0.00           H  
HETATM   49  H26 UNL     1       5.825  -2.342   0.578  1.00  0.00           H  
HETATM   50  H27 UNL     1       4.107  -2.774   0.849  1.00  0.00           H  
HETATM   51  H28 UNL     1       5.298   1.441  -2.176  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    9
CONECT    3    4    5
CONECT    4   27   28   29
CONECT    5    6    6   23
CONECT    6    7   11
CONECT    7    8    9    9
CONECT    8   30   31   32
CONECT    9   10
CONECT   10   33
CONECT   11   12   34   35
CONECT   12   13   36   37
CONECT   13   14   15   23
CONECT   14   38   39   40
CONECT   15   16   41   42
CONECT   16   17   43   44
CONECT   17   18   45   46
CONECT   18   19   20   47
CONECT   19   48   49   50
CONECT   20   21   21   22
CONECT   22   51
END

HMDB0012798
     RDKit          3D
5'-Carboxy-alpha-chromanol
 51 52  0  0  0  0  0  0  0  0999 V2000
   -4.1410   -2.4570   -1.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4913   -1.2448   -0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1535   -1.0755   -0.8462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2729   -2.0810   -1.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6053    0.0878   -0.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3934    1.0499    0.2822 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7248    0.8740    0.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5025    1.9475    1.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3039   -0.2904   -0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6448   -0.5164    0.0497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6770    2.2451    0.7831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4784    1.7592    1.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    1.0786    0.5458 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2159    2.1951   -0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2362    0.0896    1.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2319   -0.7895    0.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3643   -0.0575    0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3436   -1.1044   -0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8066   -1.9287    0.7264 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4425   -0.3718   -1.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6310   -0.4857   -0.7031 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1389    0.4616   -2.1447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2654    0.3915   -0.4273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8087   -2.1859   -2.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7797   -2.9390   -0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4183   -3.2129   -1.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5732   -2.2358   -2.5686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2321   -1.7060   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116   -3.0637   -0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1678    2.9247    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5753    1.8683    0.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2800    1.9565    2.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3085    0.0872    0.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4077    2.9006   -0.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3234    2.8832    1.4459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880    1.0122    2.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0630    2.6100    1.9956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5910    3.1413    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1688    2.4776    0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3855    2.1323   -1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7517    0.6196    2.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4967   -0.5664    1.9068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7078   -1.3831    1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8256   -1.6054    0.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8847    0.5312    0.8899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0903    0.6435   -0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7906   -1.6766   -1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7512   -1.3163    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8249   -2.3415    0.5776 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1068   -2.7741    0.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2983    1.4412   -2.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 13 23  1  0
  9  2  1  0
 23  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 22 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
alpha-CMBHC	MeSH
5'-Carboxy-alpha-tocopherol	HMDB
5-[(2R)-6-Hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2-methylpentanoate	Generator

Chemical Formula

C₁₉H₂₈O₄

Average Molecular Weight

320.4232

Monoisotopic Molecular Weight

320.198759384

IUPAC Name

5-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-yl]-2-methylpentanoic acid

Traditional Name

5-[(2R)-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-1-benzopyran-2-yl]-2-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)C(O)=O

InChI Identifier

InChI=1S/C19H28O4/c1-11(18(21)22)7-6-9-19(5)10-8-15-14(4)16(20)12(2)13(3)17(15)23-19/h11,20H,6-10H2,1-5H3,(H,21,22)/t11?,19-/m1/s1

InChI Key

QWPNLVBAEZJBMI-IMFVZPHKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Medium-chain fatty acid
Alkyl aryl ether
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Ether
Oxacycle
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.038 g/L	ALOGPS
logP	4.16	ALOGPS
logP	5.31	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	91.16 m³·mol⁻¹	ChemAxon
Polarizability	36.96 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	176.487	31661259
DarkChem	[M-H]-	173.309	31661259
DeepCCS	[M+H]+	181.568	30932474
DeepCCS	[M-H]-	179.21	30932474
DeepCCS	[M-2H]-	213.332	30932474
DeepCCS	[M+Na]+	189.035	30932474
AllCCS	[M+H]+	179.3	32859911
AllCCS	[M+H-H2O]+	176.2	32859911
AllCCS	[M+NH4]+	182.2	32859911
AllCCS	[M+Na]+	183.0	32859911
AllCCS	[M-H]-	185.9	32859911
AllCCS	[M+Na-2H]-	186.3	32859911
AllCCS	[M+HCOO]-	186.9	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.	7.76 minutes	32390414
Predicted by Siyang on May 30, 2022	18.1408 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.88 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	31.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2403.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	448.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	214.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	215.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	306.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	971.0 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	918.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	81.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1542.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	577.3 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	1826.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	547.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	439.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	351.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	373.2 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	9.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5'-Carboxy-alpha-chromanol	CC(CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)C(O)=O	3783.0	Standard polar	33892256
5'-Carboxy-alpha-chromanol	CC(CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)C(O)=O	2572.5	Standard non polar	33892256
5'-Carboxy-alpha-chromanol	CC(CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C)C(O)=O	2620.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5'-Carboxy-alpha-chromanol,1TMS,isomer #1	CC1=C(C)C2=C(CC[C@@](C)(CCCC(C)C(=O)O)O2)C(C)=C1O[Si](C)(C)C	2586.7	Semi standard non polar	33892256
5'-Carboxy-alpha-chromanol,1TMS,isomer #2	CC1=C(C)C2=C(CC[C@@](C)(CCCC(C)C(=O)O[Si](C)(C)C)O2)C(C)=C1O	2490.7	Semi standard non polar	33892256
5'-Carboxy-alpha-chromanol,2TMS,isomer #1	CC1=C(C)C2=C(CC[C@@](C)(CCCC(C)C(=O)O[Si](C)(C)C)O2)C(C)=C1O[Si](C)(C)C	2561.8	Semi standard non polar	33892256
5'-Carboxy-alpha-chromanol,1TBDMS,isomer #1	CC1=C(C)C2=C(CC[C@@](C)(CCCC(C)C(=O)O)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	2832.3	Semi standard non polar	33892256
5'-Carboxy-alpha-chromanol,1TBDMS,isomer #2	CC1=C(C)C2=C(CC[C@@](C)(CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O	2765.8	Semi standard non polar	33892256
5'-Carboxy-alpha-chromanol,2TBDMS,isomer #1	CC1=C(C)C2=C(CC[C@@](C)(CCCC(C)C(=O)O[Si](C)(C)C(C)(C)C)O2)C(C)=C1O[Si](C)(C)C(C)(C)C	3023.7	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 - 5'-Carboxy-alpha-chromanol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a59-5193000000-21a44421397f44e8ef10	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Carboxy-alpha-chromanol GC-MS (2 TMS) - 70eV, Positive	splash10-0092-9418400000-1183546d2d9264c18b03	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5'-Carboxy-alpha-chromanol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy-alpha-chromanol 10V, Positive-QTOF	splash10-0g4i-0739000000-ca7cf4a3acdfe0598353	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy-alpha-chromanol 20V, Positive-QTOF	splash10-014i-1911000000-87257705b965ee40a7b5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy-alpha-chromanol 40V, Positive-QTOF	splash10-066r-3900000000-51c6445c30175ea5c865	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy-alpha-chromanol 10V, Negative-QTOF	splash10-014i-0019000000-e48de0e905548411c044	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy-alpha-chromanol 20V, Negative-QTOF	splash10-0i29-1798000000-b5d9e37b42b4c3fd9889	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy-alpha-chromanol 40V, Negative-QTOF	splash10-0r7j-3920000000-36465eb352f634a1d51b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy-alpha-chromanol 10V, Negative-QTOF	splash10-014i-0019000000-03b18204386c4c9d8bd4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy-alpha-chromanol 20V, Negative-QTOF	splash10-016r-0395000000-2bf38f23f39a4fa97197	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy-alpha-chromanol 40V, Negative-QTOF	splash10-0a4r-0690000000-539dacc450e163bec4e1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy-alpha-chromanol 10V, Positive-QTOF	splash10-0fi0-0096000000-6c33505488ad70d71925	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy-alpha-chromanol 20V, Positive-QTOF	splash10-004j-0090000000-366d350d1a77109facef	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5'-Carboxy-alpha-chromanol 40V, Positive-QTOF	splash10-014i-4920000000-158de22677ca15ece6b9	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Iron deficiency	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	26848182	details

Associated Disorders and Diseases

Disease References

Iron deficiency
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Ulcerative colitis
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029177

KNApSAcK ID

Not Available

Chemspider ID

35032548

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481524

PDB ID

Not Available

ChEBI ID

172549

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

Not Available

Showing metabocard for 5'-Carboxy-alpha-chromanol (HMDB0012798)

MOL for HMDB0012798 (5'-Carboxy-alpha-chromanol)

3D MOL for HMDB0012798 (5'-Carboxy-alpha-chromanol)

3D SDF for HMDB0012798 (5'-Carboxy-alpha-chromanol)

3D-SDF for HMDB0012798 (5'-Carboxy-alpha-chromanol)

PDB for HMDB0012798 (5'-Carboxy-alpha-chromanol)

3D PDB for HMDB0012798 (5'-Carboxy-alpha-chromanol)

SMILES for HMDB0012798 (5'-Carboxy-alpha-chromanol)

INCHI for HMDB0012798 (5'-Carboxy-alpha-chromanol)

Structure for HMDB0012798 (5'-Carboxy-alpha-chromanol)

3D Structure for HMDB0012798 (5'-Carboxy-alpha-chromanol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra