8-coumaroylharpagide

ID: ALA513852

Cas Number: 87686-74-6

PubChem CID: 10324058

Max Phase: Preclinical

Molecular Formula: C24H30O12

Molecular Weight: 510.49

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 8-Coumaroylharpagide | 8-p-Coumaroylharpagide|87686-74-6|8-coumaroylharpagide|CHEMBL513852|8-O-4-Hydroxycinnamoylharpagide, >=95% (LC/MS-ELSD)|[(1S,4aS,5R,7S,7aS)-4a,5-dihydroxy-7-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate

Canonical SMILES:  C[C@]1(OC(=O)/C=C/c2ccc(O)cc2)C[C@@H](O)[C@]2(O)C=CO[C@@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H]21

Standard InChI:  InChI=1S/C24H30O12/c1-23(36-16(28)7-4-12-2-5-13(26)6-3-12)10-15(27)24(32)8-9-33-22(20(23)24)35-21-19(31)18(30)17(29)14(11-25)34-21/h2-9,14-15,17-22,25-27,29-32H,10-11H2,1H3/b7-4+/t14-,15-,17-,18+,19-,20-,21+,22+,23+,24-/m1/s1

Standard InChI Key:  AZKQDXZMKREFDY-CBLWINFVSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA513852

   8-p-Coumaroylharpagide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 510.49

Molecular Weight (Monoisotopic): 510.1737

AlogP: -1.49

#Rotatable Bonds: 6

Polar Surface Area: 195.60

Molecular Species: NEUTRAL

HBA: 12

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.40

CX Basic pKa: ┄

CX LogP: -1.17

CX LogD: -1.17

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.17

Np Likeness Score: 2.58

References

1. Abdelouahab N, Heard C..  (2008)  Effect of the major glycosides of Harpagophytum procumbens (Devil's Claw) on epidermal cyclooxygenase-2 (COX-2) in vitro.,  71  (5): [PMID:18412394] [10.1021/np070204u]

Source

Source(1):

• Scientific Literature