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

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014578

Secondary Accession Numbers

HMDB14578

Metabolite Identification

Common Name

Cyproheptadine

Description

Cyproheptadine, also known as ciprovit or antergan, belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring. Cyproheptadine is a drug which is used for treatment of perennial and seasonal allergic rhinitis, vasomotor rhinitis, allergic conjunctivitis due to inhalant allergens and foods, mild uncomplicated allergic skin manifestations of urticaria and angioedema, amelioration of allergic reactions to blood or plasma, cold urticaria, dermatographism, and as therapy for anaphylactic reactions adjunctive to epinephrine. Cyproheptadine is a very strong basic compound (based on its pKa). In humans, cyproheptadine is involved in cyproheptadine h1-antihistamine action. It is a sedating antihistamine with antimuscarinic and calcium-channel blocking actions. Unlike other antihistamines, it is also a seratonin receptor antagonist, making it useful in conditions such as vascular headache and anorexia. The product resulting from the formal oxidative coupling of position 5 of 5H-dibenzocycloheptene with position 4 of 1-methylpiperidine resulting in the formation of a double bond between the two fragments. Cyproheptadine is a potentially toxic compound. It is used (particularly as the hydrochloride sesquihydrate) for the relief of allergic conditions including rhinitis, conjunctivitis due to inhalant allergens and foods, urticaria and angioedema, and in pruritic skin disorders.

Structure

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

HMDB0014578
     RDKit          3D
Cyproheptadine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.7164    0.0435   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5874    0.4887   -0.9150 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7980   -0.5955   -1.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7137   -1.0687   -0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7041    0.0317   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5343   -0.0700    0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3181    1.1784    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6448    2.0801    1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2186    3.2845    1.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4718    3.5631    0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613    2.6641   -0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777    1.4562   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4308    0.5476   -1.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -0.7901   -1.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448   -1.6755   -0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8674   -2.9745   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031   -3.9178    0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8795   -3.5504    0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4218   -2.2584    0.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2223   -1.3775    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472    1.3327   -0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565    1.4271   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5108   -0.9831    0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6580    0.0952   -0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8609    0.7072    0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4937   -1.4883   -1.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740   -0.4048   -2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3128   -1.2929    0.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -1.9412   -0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    1.7357    1.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6861    4.0018    1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064    4.5287    0.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542    2.8619   -0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973    1.0025   -1.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0935   -1.3012   -1.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8253   -3.2651   -0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4481   -4.9605    0.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2749   -4.2742    1.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705   -1.8593    1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7684    2.2053   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5022    1.1516   -1.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1142    2.4600   -0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9002    1.2016    0.8986 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  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  5 21  1  0
 21 22  1  0
 22  2  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END

434
  Mrv0541 02231214402D          

 22 25  0  0  0  0            999 V2000
    4.0285   -1.7286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0285   -0.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7429   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140   -0.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7429   -1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139   -1.3161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0285    0.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7718    1.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2852    1.1043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0285   -2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9554    1.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1016    1.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3926    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6643    0.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4410    2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6160    2.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7725    2.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2844    2.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2157    0.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8412    0.7571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4070    1.5949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.5950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  6  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  7  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  1  0  0  0  0
  8 13  2  0  0  0  0
  9 12  1  0  0  0  0
  9 14  2  0  0  0  0
 11 15  1  0  0  0  0
 11 17  2  0  0  0  0
 12 16  1  0  0  0  0
 12 18  2  0  0  0  0
 13 19  1  0  0  0  0
 14 20  1  0  0  0  0
 15 16  2  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014578

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC(CC1)=C1C2=CC=CC=C2C=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C21H21N/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21/h2-11H,12-15H2,1H3

> <INCHI_KEY>
JJCFRYNCJDLXIK-UHFFFAOYSA-N

> <FORMULA>
C21H21N

> <MOLECULAR_WEIGHT>
287.3981

> <EXACT_MASS>
287.167399677

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
34.16864145048664

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-4-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-ylidene}piperidine

> <ALOGPS_LOGP>
5.02

> <JCHEM_LOGP>
4.382841646999999

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.049354685511974

> <JCHEM_POLAR_SURFACE_AREA>
3.24

> <JCHEM_REFRACTIVITY>
105.17420000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
periactin

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014578
     RDKit          3D
Cyproheptadine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.7164    0.0435   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5874    0.4887   -0.9150 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7980   -0.5955   -1.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7137   -1.0687   -0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7041    0.0317   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5343   -0.0700    0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3181    1.1784    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6448    2.0801    1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2186    3.2845    1.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4718    3.5631    0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613    2.6641   -0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777    1.4562   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4308    0.5476   -1.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -0.7901   -1.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448   -1.6755   -0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8674   -2.9745   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031   -3.9178    0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8795   -3.5504    0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4218   -2.2584    0.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2223   -1.3775    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472    1.3327   -0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565    1.4271   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5108   -0.9831    0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6580    0.0952   -0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8609    0.7072    0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4937   -1.4883   -1.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740   -0.4048   -2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3128   -1.2929    0.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -1.9412   -0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    1.7357    1.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6861    4.0018    1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064    4.5287    0.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542    2.8619   -0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973    1.0025   -1.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0935   -1.3012   -1.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8253   -3.2651   -0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4481   -4.9605    0.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2749   -4.2742    1.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705   -1.8593    1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7684    2.2053   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5022    1.1516   -1.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1142    2.4600   -0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9002    1.2016    0.8986 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  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  5 21  1  0
 21 22  1  0
 22  2  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 434                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       7.520  -3.227   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       7.520  -0.147   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.853  -0.917   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.186  -0.917   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.853  -2.457   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.186  -2.457   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.520   1.393   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.907   2.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.132   2.061   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.520  -4.767   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.250   3.563   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.790   3.563   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.066   0.952   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.973   0.952   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.290   4.767   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.750   4.767   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.775   4.059   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.264   4.059   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.603   1.413   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.437   1.413   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.960   2.977   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080   2.977   0.000  0.00  0.00           C+0
CONECT    1    5    6   10                                                  
CONECT    2    3    4    7                                                  
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    1    3                                                       
CONECT    6    1    4                                                       
CONECT    7    2    8    9                                                  
CONECT    8    7   11   13                                                  
CONECT    9    7   12   14                                                  
CONECT   10    1                                                            
CONECT   11    8   15   17                                                  
CONECT   12    9   16   18                                                  
CONECT   13    8   19                                                       
CONECT   14    9   20                                                       
CONECT   15   11   16                                                       
CONECT   16   12   15                                                       
CONECT   17   11   21                                                       
CONECT   18   12   22                                                       
CONECT   19   13   21                                                       
CONECT   20   14   22                                                       
CONECT   21   17   19                                                       
CONECT   22   18   20                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0014578
HETATM    1  C1  UNL     1       4.716   0.044  -0.157  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.587   0.489  -0.915  1.00  0.00           N  
HETATM    3  C2  UNL     1       2.798  -0.596  -1.441  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.714  -1.069  -0.466  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.704   0.032  -0.242  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.534  -0.070   0.070  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.318   1.178   0.251  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.645   2.080   1.019  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.219   3.285   1.267  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.472   3.563   0.734  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.161   2.664  -0.037  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.578   1.456  -0.281  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.431   0.548  -1.071  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.395  -0.790  -1.162  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.445  -1.676  -0.454  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.867  -2.975  -0.343  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.103  -3.918   0.317  1.00  0.00           C  
HETATM   18  C17 UNL     1      -0.880  -3.550   0.884  1.00  0.00           C  
HETATM   19  C18 UNL     1      -0.422  -2.258   0.796  1.00  0.00           C  
HETATM   20  C19 UNL     1      -1.222  -1.377   0.128  1.00  0.00           C  
HETATM   21  C20 UNL     1       1.347   1.333  -0.656  1.00  0.00           C  
HETATM   22  C21 UNL     1       2.756   1.427  -0.156  1.00  0.00           C  
HETATM   23  H1  UNL     1       4.511  -0.983   0.204  1.00  0.00           H  
HETATM   24  H2  UNL     1       5.658   0.095  -0.771  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.861   0.707   0.727  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.494  -1.488  -1.508  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.474  -0.405  -2.442  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.313  -1.293   0.444  1.00  0.00           H  
HETATM   29  H7  UNL     1       1.270  -1.941  -0.897  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.318   1.736   1.415  1.00  0.00           H  
HETATM   31  H9  UNL     1      -0.686   4.002   1.873  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.906   4.529   0.945  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.154   2.862  -0.469  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.197   1.003  -1.661  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.094  -1.301  -1.783  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.825  -3.265  -0.787  1.00  0.00           H  
HETATM   37  H15 UNL     1      -2.448  -4.960   0.401  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.275  -4.274   1.399  1.00  0.00           H  
HETATM   39  H17 UNL     1       0.470  -1.859   1.234  1.00  0.00           H  
HETATM   40  H18 UNL     1       0.768   2.205  -0.633  1.00  0.00           H  
HETATM   41  H19 UNL     1       1.502   1.152  -1.804  1.00  0.00           H  
HETATM   42  H20 UNL     1       3.114   2.460  -0.338  1.00  0.00           H  
HETATM   43  H21 UNL     1       2.900   1.202   0.899  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   22
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6    6   21
CONECT    6    7   20
CONECT    7    8    8   12
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   12   13
CONECT   13   14   14   34
CONECT   14   15   35
CONECT   15   16   16   20
CONECT   16   17   36
CONECT   17   18   18   37
CONECT   18   19   38
CONECT   19   20   20   39
CONECT   21   22   40   41
CONECT   22   42   43
END

HMDB0014578
     RDKit          3D
Cyproheptadine
 43 46  0  0  0  0  0  0  0  0999 V2000
    4.7164    0.0435   -0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5874    0.4887   -0.9150 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7980   -0.5955   -1.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7137   -1.0687   -0.4665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7041    0.0317   -0.2422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5343   -0.0700    0.0703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3181    1.1784    0.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6448    2.0801    1.0191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2186    3.2845    1.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4718    3.5631    0.7345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1613    2.6641   -0.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777    1.4562   -0.2811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4308    0.5476   -1.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -0.7901   -1.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448   -1.6755   -0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8674   -2.9745   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1031   -3.9178    0.3165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8795   -3.5504    0.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4218   -2.2584    0.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2223   -1.3775    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3472    1.3327   -0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7565    1.4271   -0.1562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5108   -0.9831    0.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6580    0.0952   -0.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8609    0.7072    0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4937   -1.4883   -1.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4740   -0.4048   -2.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3128   -1.2929    0.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -1.9412   -0.8971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    1.7357    1.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6861    4.0018    1.8728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9064    4.5287    0.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1542    2.8619   -0.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1973    1.0025   -1.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0935   -1.3012   -1.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8253   -3.2651   -0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4481   -4.9605    0.4006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2749   -4.2742    1.3990 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4705   -1.8593    1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7684    2.2053   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5022    1.1516   -1.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1142    2.4600   -0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9002    1.2016    0.8986 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  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  5 21  1  0
 21 22  1  0
 22  2  1  0
 20  6  1  0
 12  7  1  0
 20 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 21 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Methyl-4-(5-dibenzo(a,e)cycloheptatrienylidene)piperidine	ChEBI
1-Methyl-4-(5H-dibenzo(a,D)cycloheptenylidene)piperidine	ChEBI
4-(5-Dibenzo(a,D)cyclohepten-5-ylidine)-1-methylpiperidine	ChEBI
4-(5H-Dibenzo(a,D)cyclohepten-5-ylidene)-1-methylpiperidine	ChEBI
4-Dibenzo[a,D]cyclohepten-5-ylidene-1-methyl-piperidine	ChEBI
5-(1-Methylpiperidylidene-4)-5H-dibenzo(a,D)cyclopheptene	ChEBI
Ciproheptadina	ChEBI
Cyproheptadinum	ChEBI
Ciprovit	Kegg
Antergan	HMDB
Periactin	HMDB
Peritol	HMDB
Viternum	HMDB
Dihexazin	HMDB

Chemical Formula

C₂₁H₂₁N

Average Molecular Weight

287.3981

Monoisotopic Molecular Weight

287.167399677

IUPAC Name

1-methyl-4-{tricyclo[9.4.0.0³,⁸]pentadeca-1(15),3,5,7,9,11,13-heptaen-2-ylidene}piperidine

Traditional Name

periactin

CAS Registry Number

129-03-3

SMILES

CN1CCC(CC1)=C1C2=CC=CC=C2C=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C21H21N/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21/h2-11H,12-15H2,1H3

InChI Key

JJCFRYNCJDLXIK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzocycloheptenes. Dibenzocycloheptenes are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Dibenzocycloheptenes

Sub Class

Not Available

Direct Parent

Dibenzocycloheptenes

Alternative Parents

Substituents

Dibenzocycloheptene
Piperidine
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

piperidines (CHEBI:4046 )
tertiary amine (CHEBI:4046 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	215 - 217 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.014 g/L	Not Available
LogP	4.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.014 g/L	ALOGPS
logP	5.02	ALOGPS
logP	4.38	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	8.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	3.24 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	105.17 m³·mol⁻¹	ChemAxon
Polarizability	34.17 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	169.6	31661259
DarkChem	[M-H]-	169.524	31661259
DeepCCS	[M-2H]-	197.765	30932474
DeepCCS	[M+Na]+	173.33	30932474
AllCCS	[M+H]+	170.2	32859911
AllCCS	[M+H-H2O]+	166.6	32859911
AllCCS	[M+NH4]+	173.5	32859911
AllCCS	[M+Na]+	174.4	32859911
AllCCS	[M-H]-	178.3	32859911
AllCCS	[M+Na-2H]-	177.4	32859911
AllCCS	[M+HCOO]-	176.5	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	11.3823 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.36 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	40.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1644.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	260.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	177.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	135.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	436.0 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	461.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	419.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1073.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	358.1 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	1137.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	287.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	313.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	309.3 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	7.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyproheptadine	CN1CCC(CC1)=C1C2=CC=CC=C2C=CC2=CC=CC=C12	3727.3	Standard polar	33892256
Cyproheptadine	CN1CCC(CC1)=C1C2=CC=CC=C2C=CC2=CC=CC=C12	2420.2	Standard non polar	33892256
Cyproheptadine	CN1CCC(CC1)=C1C2=CC=CC=C2C=CC2=CC=CC=C12	2423.3	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 - Cyproheptadine GC-MS (Non-derivatized) - 70eV, Positive	splash10-05g0-1090000000-7d19fca2a65a93c449d6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyproheptadine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00kr-2290000000-a17c27a9f171b058f2c3	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 - Cyproheptadine LC-ESI-qTof , Positive-QTOF	splash10-000i-0290000000-964629904e89d79568d8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyproheptadine , positive-QTOF	splash10-000i-0290000000-964629904e89d79568d8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Cyproheptadine 35V, Positive-QTOF	splash10-000m-6790000000-4e9938638118593eb406	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproheptadine 10V, Positive-QTOF	splash10-000i-1090000000-3117ec5d9639f751f7b7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproheptadine 20V, Positive-QTOF	splash10-000i-3290000000-2935111fa6fa07111de6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproheptadine 40V, Positive-QTOF	splash10-00r6-9370000000-df84a6a14decead8dedf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproheptadine 10V, Negative-QTOF	splash10-000i-0090000000-78685e74ff4bff75d39b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproheptadine 20V, Negative-QTOF	splash10-000i-0090000000-cb222eada7f0bf316df6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproheptadine 40V, Negative-QTOF	splash10-022i-5190000000-4e162fb598e8db9d6e77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproheptadine 10V, Positive-QTOF	splash10-000i-0090000000-107477c8d28ce3506c90	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproheptadine 20V, Positive-QTOF	splash10-000i-0090000000-c2a155a089dd265a5433	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproheptadine 40V, Positive-QTOF	splash10-05mo-4190000000-eaa52ca5faae687ab50f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproheptadine 10V, Negative-QTOF	splash10-000i-0090000000-26c7f893d45bf33544e2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproheptadine 20V, Negative-QTOF	splash10-000i-0090000000-2c051f1f630ec47ecb1c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyproheptadine 40V, Negative-QTOF	splash10-00lr-0090000000-012e0121acf874e7bd11	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Cyproheptadine H1-Antihistamine Action		Not Available

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 DB00434	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00434	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

DB00434

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2810

KEGG Compound ID

C06935

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cyproheptadine

METLIN ID

Not Available

PubChem Compound

2913

PDB ID

Not Available

ChEBI ID

4046

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

Tokunaga S, Takeda Y, Shinomiya K, Hirase M, Kamei C: Effects of some H1-antagonists on the sleep-wake cycle in sleep-disturbed rats. J Pharmacol Sci. 2007 Feb;103(2):201-6. Epub 2007 Feb 8. [PubMed:17287588 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-3

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:: UGT1A3
Uniprot ID:: P35503
Molecular weight:: 60337.835

References

Green MD, King CD, Mojarrabi B, Mackenzie PI, Tephly TR: Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metab Dispos. 1998 Jun;26(6):507-12. [PubMed:9616184 ]

Enzyme Details

2. 5-hydroxytryptamine receptor 2A

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:: HTR2A
Uniprot ID:: P28223
Molecular weight:: 52602.6

References

Rashid M, Nakazawa M, Nagatomo T: Effects of sarpogrelate, a novel 5-HT2 antagonist, on 5-HT-induced endothelium-dependent relaxations in porcine coronary artery. Jpn J Pharmacol. 2002 Aug;89(4):405-12. [PubMed:12233819 ]
Honda M, Nishida T, Ono H: Tricyclic analogs cyclobenzaprine, amitriptyline and cyproheptadine inhibit the spinal reflex transmission through 5-HT(2) receptors. Eur J Pharmacol. 2003 Jan 1;458(1-2):91-9. [PubMed:12498911 ]
Callaway CW, Rempel N, Peng RY, Geyer MA: Serotonin 5-HT1-like receptors mediate hyperactivity in rats induced by 3,4-methylenedioxymethamphetamine. Neuropsychopharmacology. 1992 Sep;7(2):113-27. [PubMed:1358088 ]
Hoenicke EM, Vanecek SA, Woods JH: The discriminative stimulus effects of clozapine in pigeons: involvement of 5-hydroxytryptamine1C and 5-hydroxytryptamine2 receptors. J Pharmacol Exp Ther. 1992 Oct;263(1):276-84. [PubMed:1403790 ]
Calka O, Metin A, Dulger H, Erkoc R: Effect of cyproheptadine on serum leptin levels. Adv Ther. 2005 Sep-Oct;22(5):424-8. [PubMed:16418149 ]

Enzyme Details

3. 5-hydroxytryptamine receptor 2C

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system
Gene Name:: HTR2C
Uniprot ID:: P28335
Molecular weight:: 51820.7

References

Honda M, Nishida T, Ono H: Tricyclic analogs cyclobenzaprine, amitriptyline and cyproheptadine inhibit the spinal reflex transmission through 5-HT(2) receptors. Eur J Pharmacol. 2003 Jan 1;458(1-2):91-9. [PubMed:12498911 ]

Enzyme Details

4. Histamine H1 receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:: HRH1
Uniprot ID:: P35367
Molecular weight:: 55783.6

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

5. Muscarinic acetylcholine receptor M3

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM3
Uniprot ID:: P20309
Molecular weight:: 66127.4

References

Eltze M, Lambrecht G, Mutschler E: Cyproheptadine displays high affinity for muscarinic receptors but does not discriminate between receptor subtypes. Eur J Pharmacol. 1989 Dec 7;173(2-3):219-22. [PubMed:2625138 ]

Enzyme Details

6. Muscarinic acetylcholine receptor M1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

References

Eltze M, Lambrecht G, Mutschler E: Cyproheptadine displays high affinity for muscarinic receptors but does not discriminate between receptor subtypes. Eur J Pharmacol. 1989 Dec 7;173(2-3):219-22. [PubMed:2625138 ]

Enzyme Details

7. Muscarinic acetylcholine receptor M2

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition
Gene Name:: CHRM2
Uniprot ID:: P08172
Molecular weight:: 51714.6

References

Eltze M, Lambrecht G, Mutschler E: Cyproheptadine displays high affinity for muscarinic receptors but does not discriminate between receptor subtypes. Eur J Pharmacol. 1989 Dec 7;173(2-3):219-22. [PubMed:2625138 ]

Showing metabocard for Cyproheptadine (HMDB0014578)

MOL for HMDB0014578 (Cyproheptadine)

3D MOL for HMDB0014578 (Cyproheptadine)

3D SDF for HMDB0014578 (Cyproheptadine)

3D-SDF for HMDB0014578 (Cyproheptadine)

PDB for HMDB0014578 (Cyproheptadine)

3D PDB for HMDB0014578 (Cyproheptadine)

SMILES for HMDB0014578 (Cyproheptadine)

INCHI for HMDB0014578 (Cyproheptadine)

Structure for HMDB0014578 (Cyproheptadine)

3D Structure for HMDB0014578 (Cyproheptadine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References