10-hydroxygambogic acid

ID: ALA2205164

Chembl Id: CHEMBL2205164

PubChem CID: 71450485

Max Phase: Preclinical

Molecular Formula: C38H46O9

Molecular Weight: 646.78

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 10-Hydroxygambogic Acid | 10-Hydroxygambogic Acid|CHEMBL2205164

Canonical SMILES:  CC(C)=CCC[C@]1(C)C=Cc2c(O)c3c(c(CC=C(C)C)c2O1)O[C@]12C(C3=O)C(O)[C@@H]3C[C@H]1C(C)(C)O[C@@]2(C/C=C(/C)C(=O)O)C3=O

Standard InChI:  InChI=1S/C38H46O9/c1-19(2)10-9-15-36(8)16-14-22-28(39)26-30(41)27-29(40)24-18-25-35(6,7)47-37(33(24)42,17-13-21(5)34(43)44)38(25,27)46-32(26)23(31(22)45-36)12-11-20(3)4/h10-11,13-14,16,24-25,27,29,39-40H,9,12,15,17-18H2,1-8H3,(H,43,44)/b21-13-/t24-,25-,27?,29?,36+,37-,38-/m0/s1

Standard InChI Key:  LJUARHDVFLLQMF-YLTLRVAWSA-N

Alternative Forms

1. Parent:

   

   ALA2205164

   10-Hydroxygambogic Acid

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: 646.78

Molecular Weight (Monoisotopic): 646.3142

AlogP: 6.29

#Rotatable Bonds: 8

Polar Surface Area: 139.59

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.54

CX Basic pKa: ┄

CX LogP: 6.86

CX LogD: 3.47

Aromatic Rings: 1

Heavy Atoms: 47

QED Weighted: 0.22

Np Likeness Score: 3.50

References

1. Yang J, Li C, Ding L, Guo Q, You Q, Jin S..  (2012)  Gambogic acid deactivates cytosolic and mitochondrial thioredoxins by covalent binding to the functional domain.,  75  (6): [PMID:22663155] [10.1021/np300118c]

2. Yang J, Ding L, Hu L, Qian W, Jin S, Sun X, Wang Z, Xiao W..  (2011)  Metabolism of gambogic acid in rats: a rare intestinal metabolic pathway responsible for its final disposition.,  39  (4): [PMID:21191083] [10.1124/dmd.110.037044]

Source

Source(1):

• Scientific Literature