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Details

Stereochemistry ABSOLUTE
Molecular Formula C38H44O8
Molecular Weight 628.7512
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of GAMBOGIC ACID

SMILES

CC(C)=CCC[C@@]1(C)OC2=C(C=C1)C(O)=C3C(=O)C4=C[C@@H]5C[C@H]6C(C)(C)O[C@@](C\C=C(\C)C(O)=O)(C5=O)[C@@]46OC3=C2CC=C(C)C

InChI

InChIKey=GEZHEQNLKAOMCA-RRZNCOCZSA-N
InChI=1S/C38H44O8/c1-20(2)10-9-15-36(8)16-14-24-29(39)28-30(40)26-18-23-19-27-35(6,7)46-37(33(23)41,17-13-22(5)34(42)43)38(26,27)45-32(28)25(31(24)44-36)12-11-21(3)4/h10-11,13-14,16,18,23,27,39H,9,12,15,17,19H2,1-8H3,(H,42,43)/b22-13-/t23-,27+,36-,37+,38-/m1/s1

HIDE SMILES / InChI

Molecular Formula C38H44O8
Molecular Weight 628.7512
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Gambogic acid (GA), a naturally occurring xanthone-based moiety, reported from Garcinia hanburyi tree, is known to perform numerous intracellular and extracellular actions, including programmed cell death, autophagy, cell cycle arrest, antiangiogenesis, antimetastatic, and anti-inflammatory activities. In addition, GA-based synergistic approaches have been proven to enhance the healing strength of existing chemotherapeutic agents along with lesser side effects. Among cellular targets of gambogic acid topoisomerase, multidrug-resistant protein ATP-binding cassette transporter B1 (ABCB1) and Transferrin receptor.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
6.3 µM [IC50]
50.0 µM [IC50]
3.6 µM [Ki]
25.0 µM [IC50]
2.2 µM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
The animals in the treatment group received one of three dosages of gambogic acid (in saline; 5, 10 or 20 mg/kg) via the caudal vein twice weekly. For intraperitoneal administration the mice were randomly assigned to treatment with 10, 20 or 30 mg/kg gambogic acid for 3 weeks.
Route of Administration: Other
In Vitro Use Guide
Gambogic acid displays potent antiproliferative activity against a wide panel of human tumors without distinct selectivity among the cells lines tested. The average IC50 of GA against the 21 cell lines was 1.23 μmol/L.
Substance Class Chemical
Record UNII
8N585K83U2
Record Status Validated (UNII)
Record Version