Gambogic acid 10beta-sulfonic acid

ID: ALA2205162

Chembl Id: CHEMBL2205162

PubChem CID: 71459532

Max Phase: Preclinical

Molecular Formula: C38H46O11S

Molecular Weight: 710.84

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Gambogic Acid 10Beta-Sulfonic Acid | CHEMBL2205162|Gambogic Acid 10Beta-Sulfonic Acid

Canonical SMILES:  CC(C)=CCC[C@]1(C)C=Cc2c(O)c3c(c(CC=C(C)C)c2O1)O[C@]12C(C3=O)[C@@H](S(=O)(=O)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/C38H46O11S/c1-19(2)10-9-15-36(8)16-14-22-28(39)26-29(40)27-32(50(44,45)46)24-18-25-35(6,7)49-37(33(24)41,17-13-21(5)34(42)43)38(25,27)48-31(26)23(30(22)47-36)12-11-20(3)4/h10-11,13-14,16,24-25,27,32,39H,9,12,15,17-18H2,1-8H3,(H,42,43)(H,44,45,46)/b21-13-/t24-,25-,27?,32-,36+,37-,38-/m0/s1

Standard InChI Key:  VYZBIJXUFDJCGJ-NJKZPDKSSA-N

Alternative Forms

1. Parent:

   

   ALA2205162

   Gambogic Acid 10Beta-Sulfonic 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: 710.84

Molecular Weight (Monoisotopic): 710.2761

AlogP: 6.19

#Rotatable Bonds: 9

Polar Surface Area: 173.73

Molecular Species: ACID

HBA: 9

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -1.23

CX Basic pKa: ┄

CX LogP: 6.72

CX LogD: 0.90

Aromatic Rings: 1

Heavy Atoms: 50

QED Weighted: 0.15

Np Likeness Score: 3.26

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