Drug Information

General Information of This Drug
Drug ID DRG00030
Drug Name Gambogic acid
Synonyms
gambogic acid; 2752-65-0; (-)-Gambogic Acid; Gambogic-acid; R-gambogic acid; beta-Guttiferin; Cambogic acid; B''-Guttiferin; 8N585K83U2; .beta.-Guttiferin; GAMBOGICACID; (Z)-4-((1S,3aR,5S,11R,14aS)-8-hydroxy-2,2,11-trimethyl-13-(3-methylbut-2-en-1-yl)-11-(4-methylpent-3-en-1-yl)-4,7-dioxo-1,2,5,7-tetrahydro-11H-1,5-methanofuro[3,2-g]pyrano[3,2-b]xanthen-3a(4H)-yl)-2-methylbut-2-enoic acid; CHEBI:67521; UNII-8N585K83U2; GAMBOGIC ACID [MI]; CHEMBL555017; CHEMBL5305342; SCHEMBL16160279; GEZHEQNLKAOMCA-RRZNCOCZSA-N; DTXSID101029723; GLXC-02792; BCP21539; HY-N0087; BDBM50366237; MFCD16878985; s2448; AKOS024463359; CCG-270284; CS-1456; AC-34804; BP-22199; Gambogic acid, >=95% (HPLC), powder; H10129; Q5519727; (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; (Z)-4-[(1S,2S,8R,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoic acid; 1,5-Methano-1H,3H,11H-furo(3,4-g)pyrano(3,2-b)xanthene-1-crotonic acid, 3a,4,5,7-tetrahydro-8-hydroxy-alpha,3,3,11-tetramethyl-13-(3-methyl-2-butenyl)-11-(4-methyl-3-pentenyl)-7,15-dioxo-, (Z)-; 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)-
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Structure
Formula
C38H44O8
#Ro5 Violations (Lipinski): 2 Molecular Weight (mw) 628.7
Lipid-water partition coefficient (xlogp) 7.3
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 8
Rotatable Bond Count (rotbonds) 8
PubChem CID
9852185
Canonical smiles
CC(=CCCC1(C=CC2=C(C3=C(C(=C2O1)CC=C(C)C)OC45C6CC(C=C4C3=O)C(=O)C5(OC6(C)C)CC=C(C)C(=O)O)O)C)C
InChI
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
InChIKey
GEZHEQNLKAOMCA-RRZNCOCZSA-N
IUPAC Name
(Z)-4-[(1S,2S,8R,17S,19R)-12-hydroxy-8,21,21-trimethyl-5-(3-methylbut-2-enyl)-8-(4-methylpent-3-enyl)-14,18-dioxo-3,7,20-trioxahexacyclo[15.4.1.02,15.02,19.04,13.06,11]docosa-4(13),5,9,11,15-pentaen-19-yl]-2-methylbut-2-enoic acid
The activity data of This Drug
Standard Type Value Administration times Cell line Cell line ID Ref.
Half Maximal Inhibitory Concentration (IC50) 4.95 µM 24 h Bladder cancer cell N.A. [1]
Full Information of The Activity Data of The PDC(s) Related to This Drug
GA-TAT [Investigative]
 PDC Info 
Revealed Based on the Cell Line Data
Click To Hide/Show 2 Activity Data Related to This Level
Experiment 1 Reporting the Activity Data of This PDC [1]
Indication Bladder cancer
Efficacy Data Inhibition rate 46.4% ± 4.86%
Administration Time 24 h
Administration Dosage 1.0 µM
MOA of PDC
These findings suggest that GA-TAT-induced EJ cell apoptosis is mediated via ROS production. Our study demonstrated that GA-TAT enhanced the pro-apoptotic effect via increasing caspase-3 and caspase-9 processing and activities and decreasing the Bcl-2/Bax ratio, which were regulated by intracellular ROS.
Description
However, after treatment with GA-TAT, the percentage of apoptotic cells was greatly increased to 46.4%±4.86%.
In Vitro Model Bladder carcinoma EJ-1 cell CVCL_2893
Experiment 2 Reporting the Activity Data of This PDC [1]
Indication Bladder cancer
Efficacy Data Half Maximal Inhibitory Concentration (IC50) 1.24 µM
Evaluation Method MTT assay
Administration Time 24 h
MOA of PDC
These findings suggest that GA-TAT-induced EJ cell apoptosis is mediated via ROS production. Our study demonstrated that GA-TAT enhanced the pro-apoptotic effect via increasing caspase-3 and caspase-9 processing and activities and decreasing the Bcl-2/Bax ratio, which were regulated by intracellular ROS.
Description
The 50% inhibitory concentration (IC50) of GA-TAT at 24 h was 1.24 uM
In Vitro Model Bladder cancer Bladder cancer cell Homo sapiens
References
Ref 1 Cell-penetrating peptide conjugates of gambogic acid enhance the antitumor effect on human bladder cancer EJ cells through ROS-mediated apoptosis. Drug Des Devel Ther. 2018 Apr 5;12:743-756. doi: 10.2147/DDDT.S161821. eCollection 2018.