GAMBOGIC ACID

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 Search

SMILES

CC(C)=CCC[C@@]1(C)OC2=C(CC=C(C)C)C3=C(C(=O)C4=C[C@@H]5C[C@H]6C(C)(C)O[C@@](C\C=C(\C)C(O)=O)(C5=O)[C@@]46O3)C(O)=C2C=C1

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27448303
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17876042 | https://www.ncbi.nlm.nih.gov/pubmed/22759348 | https://www.ncbi.nlm.nih.gov/pubmed/16103367

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 Target	Pharmacology	Potency
DNA topoisomerase II alpha 37 Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17876042	Inhibitor 8504	6.3 µM [IC50]
DNA topoisomerase 1 16 Target ID: CHEMBL5948 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17876042	Inhibitor 8504	50.0 µM [IC50]
Cannabinoid CB2 receptor 71 Target ID: CHEMBL253 Sources: http://www.fasebj.org/content/24/1_Supplement/769.1.short?cited-by=yes&legid=fasebj%3B24%2F1_Supplement%2F769.1&trendmd-shared=1	Partial Agonist 297	3.6 µM [Ki]
26S proteosome 7 Target ID: CHEMBL2364701 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23260670	Inhibitor 8504	25.0 µM [IC50]
P-glycoprotein 1 54 Target ID: CHEMBL4302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22759348	Inhibitor 8504
Transferrin receptor protein 1 1 Target ID: P02786 Gene ID: 7037.0 Gene Symbol: TFRC Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/16103367	Modulator 846	2.2 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27448303	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Gambogic acid sensitizes resistant breast cancer cells to doxorubicin through inhibiting P-glycoprotein and suppressing survivin expression.	2015-06-25	25824409
Calcium channel blocker verapamil accelerates gambogic acid-induced cytotoxicity via enhancing proteasome inhibition and ROS generation.	2014-04	24373880
The combination of proteasome inhibitors bortezomib and gambogic acid triggers synergistic cytotoxicity in vitro but not in vivo.	2014-01-30	24291039
Gambogic acid induces G0/G1 arrest and apoptosis involving inhibition of SRC-3 and inactivation of Akt pathway in K562 leukemia cells.	2009-08-03	19433130
Reactive oxygen species accumulation contributes to gambogic acid-induced apoptosis in human hepatoma SMMC-7721 cells.	2009-06-16	19464570
Synergistic effect of 5-fluorouracil with gambogic acid on BGC-823 human gastric carcinoma.	2009-02-04	19084572
Anticancer effect and apoptosis induction of gambogic acid in human gastric cancer line BGC-823.	2005-06-28	15968715

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 Created by `admin` on `Mon Mar 31 21:56:22 GMT 2025` Edited by `admin` on `Mon Mar 31 21:56:22 GMT 2025`
Record UNII	8N585K83U2
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

GAMBOGIC ACID

Common Name

English

(-)-GAMBOGIC ACID

Preferred Name

English

.BETA.-GUTTIFERIN

Common Name

English

GAMBOGIC ACID [MI]

Common Name

English

(2Z)-2-METHYL-4-((1R,3AS,5S,11R,14AS)-3A,4,5,7-TETRAHYDRO-8-HYDROXY-3,3,11-TRIMETHYL-13-(3-METHYL-2-BUTEN-1-YL)-11-(4-METHYL-3-PENTEN-1-YL)-7,15-DIOXO-1,5-METHANO-1H,3H,11H-FURO(3,4-G)PYRANO(3,2-B)XANTHEN-1-YL)-2-BUTENOIC ACID

Systematic Name

English

2-BUTENOIC ACID, 2-METHYL-4-((1R,3AS,5S,11R,14AS)-3A,4,5,7-TETRAHYDRO-8-HYDROXY-3,3,11-TRIMETHYL-13-(3-METHYL-2-BUTEN-1-YL)-11-(4-METHYL-3-PENTEN-1-YL)-7,15-DIOXO-1,5-METHANO-1H,3H,11H-FURO(3,4-G)PYRANO(3,2-B)XANTHEN-1-YL)-, (2Z)-

Systematic Name

English

R-GAMBOGIC ACID

Common Name

English

Code System Code Type Description

CAS

2752-65-0