Gambogic Acid
Names
[ CAS No. ]:
2752-65-0
[ Name ]:
Gambogic Acid
[Synonym ]:
GUTTIC ACID
(2E)-4-[(2S,17S)-12-Hydroxy-8,21,21-trimethyl-5-(3-methyl-2-buten-1-yl)-8-(4-methyl-3-penten-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0.0.0.0]docosa-4(13),5,9,11,15-pent aen-19-yl]-2-methyl-2-butenoic acid
GUTTATIC ACID
cambogicacid
(2E)-4-[(5S,14aS)-8-hydroxy-3,3,11-trimethyl-13-(3-methylbut-2-en-1-yl)-11-(4-methylpent-3-en-1-yl)-7,15-dioxo-3a,4,5,7-tetrahydro-3H,11H-1,5-methanofuro[3,4-g]pyrano[3,2-b]xanthen-1-yl]-2-methylbut-2-enoic acid
2-Butenoic acid, 2-methyl-4-[(5S,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]-, (2E)-
Gambogic acid
(2E)-4-[(2S,17S)-12-Hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-en-1-yl)-8-(4-methylpent-3-en-1-yl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.0.0.0.0]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoic acid
Biological Activity
[Description]:
[Related Catalog]:
[Target]
Bcl-B:0.66 μM (IC50)
Mcl-1:0.79 μM (IC50)
Bfl-1:1.06 μM (IC50)
Bcl-2:1.21 μM (IC50)
Bcl-xL:1.47 μM (IC50)
Bcl-W:2.02 μM (IC50)
Autophagy
[In Vitro]
[In Vivo]
[Cell Assay]
[Animal admin]
[References]
[Related Small Molecules]
Chemical & Physical Properties
[ Density]:
1.3±0.1 g/cm3
[ Boiling Point ]:
808.9±65.0 °C at 760 mmHg
[ Melting Point ]:
88.5°C
[ Molecular Formula ]:
C38H44O8
[ Molecular Weight ]:
628.751
[ Flash Point ]:
251.4±27.8 °C
[ Exact Mass ]:
628.303589
[ PSA ]:
119.36000
[ LogP ]:
10.30
[ Vapour Pressure ]:
0.0±3.0 mmHg at 25°C
[ Index of Refraction ]:
1.627
MSDS
Toxicological Information
CHEMICAL IDENTIFICATION
- RTECS NUMBER :
- PB9268200
- CHEMICAL NAME :
- 1,5-Methano-1H,3H,11H-furo(3,4-g)pyrano(3,2-b)xanthen e-1-crotonic acid, 3a,4,5,7-tetrahydro- 8-hydroxy-alpha,3,3,11-tetramethyl-13-(3-methyl-2-but enyl)-11-(4-methyl-3- pentenyl)-7,15- dioxo-, (Z)-
- CAS REGISTRY NUMBER :
- 2752-65-0
- LAST UPDATED :
- 199503
- DATA ITEMS CITED :
- 4
- MOLECULAR FORMULA :
- C38-H44-O8
- MOLECULAR WEIGHT :
- 628.82
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 88 mg/kg
- TOXIC EFFECTS :
- Liver - other changes
- REFERENCE :
- IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 5,96,1967
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 107 mg/kg
- TOXIC EFFECTS :
- Liver - other changes
- REFERENCE :
- IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 5,96,1967
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Subcutaneous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 354 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(1),331,1982
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Unreported
- SPECIES OBSERVED :
- Mammal - species unspecified
- DOSE/DURATION :
- 55 mg/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- REFERENCE :
- 85PEAG "Zhongliu Yanjiu" Cancer Review, Yu, R., et al., eds., Shanghai Science/Technology Publisher, Peop. Rep. China, 1994 Volume(issue)/page/year: -,220,1994
Safety Information
[ Symbol ]:
GHS06
[ Signal Word ]:
Danger
[ Hazard Statements ]:
H301-H315-H319-H335
[ Precautionary Statements ]:
P261-P301 + P310-P305 + P351 + P338
[ Personal Protective Equipment ]:
Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
[ Hazard Codes ]:
T
[ Risk Phrases ]:
25-36/37/38
[ Safety Phrases ]:
26-45
[ RIDADR ]:
UN 2811 6.1 / PGIII
[ WGK Germany ]:
1.0
[ RTECS ]:
PB9268200
[ HS Code ]:
2942000000
Customs
[ HS Code ]: 2942000000
Articles
Cell Physiol. Biochem. 30(2) , 428-38, (2012)
Gambogic acid, a xanthone from Garcinia hanburyi, stimulates apoptosis and has thus anticancer potency. Similar to apoptosis of nucleated cells, erythrocytes may undergo apoptosis-like suicidal death ...
Gambogic acid as a non-competitive inhibitor of ATP-binding cassette transporter B1 reverses the multidrug resistance of human epithelial cancers by promoting ATP-binding cassette transporter B1 protein degradation.Basic Clin Pharmacol Toxicol. 112(1) , 25-33, (2013)
Gambogic acid (GA) is known for its anti-cancer activity in a phase II clinical trial. However, the detailed molecular mechanisms of its anti-multidrug resistance remain unclear. The present study was...
Subcellular localization and activity of gambogic acid.ChemBioChem. 13(8) , 1191-8, (2012)
The natural product gambogic acid (GA) has shown significant potential as an anticancer agent as it is able to induce apoptosis in multiple tumor cell lines, including multidrug-resistant cell lines, ...