Gambogic Acid

Details

Top
Internal ID e2361846-9032-4d1f-a61c-bfb6c57a3e18
Taxonomy Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > Pyranoxanthones
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
SMILES (Canonical) 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
SMILES (Isomeric) CC(=CCC[C@@]1(C=CC2=C(C3=C(C(=C2O1)CC=C(C)C)O[C@@]45[C@H]6C[C@@H](C=C4C3=O)C(=O)[C@@]5(OC6(C)C)C/C=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
InChI Key GEZHEQNLKAOMCA-RRZNCOCZSA-N
Popularity 370 references in papers

Physical and Chemical Properties

Top
Molecular Formula C38H44O8
Molecular Weight 628.70 g/mol
Exact Mass 628.30361836 g/mol
Topological Polar Surface Area (TPSA) 119.00 Ų
XlogP 7.30
Atomic LogP (AlogP) 7.24
H-Bond Acceptor 7
H-Bond Donor 2
Rotatable Bonds 8

Synonyms

Top
2752-65-0
(-)-Gambogic Acid
Gambogic-acid
Guttatic acid
R-gambogic acid
Guttic acid
beta-Guttiferin
Cambogic acid
UNII-8N585K83U2
B''-Guttiferin
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top
2D Structure of Gambogic Acid

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9738 97.38%
Caco-2 - 0.8041 80.41%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.8241 82.41%
OATP2B1 inhibitior - 0.5729 57.29%
OATP1B1 inhibitior - 0.6641 66.41%
OATP1B3 inhibitior + 0.9448 94.48%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.6000 60.00%
BSEP inhibitior + 0.9974 99.74%
P-glycoprotein inhibitior + 0.8501 85.01%
P-glycoprotein substrate + 0.6126 61.26%
CYP3A4 substrate + 0.7023 70.23%
CYP2C9 substrate - 0.6000 60.00%
CYP2D6 substrate - 0.8689 86.89%
CYP3A4 inhibition - 0.8288 82.88%
CYP2C9 inhibition - 0.5757 57.57%
CYP2C19 inhibition - 0.6867 68.67%
CYP2D6 inhibition - 0.8818 88.18%
CYP1A2 inhibition + 0.5364 53.64%
CYP2C8 inhibition + 0.7439 74.39%
CYP inhibitory promiscuity - 0.7130 71.30%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9300 93.00%
Carcinogenicity (trinary) Danger 0.4577 45.77%
Eye corrosion - 0.9916 99.16%
Eye irritation - 0.8984 89.84%
Skin irritation - 0.5828 58.28%
Skin corrosion - 0.8964 89.64%
Ames mutagenesis + 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4490 44.90%
Micronuclear - 0.6800 68.00%
Hepatotoxicity - 0.6750 67.50%
skin sensitisation - 0.7964 79.64%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.9333 93.33%
Mitochondrial toxicity + 0.8375 83.75%
Nephrotoxicity - 0.9468 94.68%
Acute Oral Toxicity (c) I 0.4789 47.89%
Estrogen receptor binding + 0.8225 82.25%
Androgen receptor binding + 0.7585 75.85%
Thyroid receptor binding + 0.6575 65.75%
Glucocorticoid receptor binding + 0.8569 85.69%
Aromatase binding + 0.7599 75.99%
PPAR gamma + 0.7339 73.39%
Honey bee toxicity - 0.7178 71.78%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5200 52.00%
Fish aquatic toxicity + 0.9955 99.55%

Targets

Top

Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL4361 Q07820 Induced myeloid leukemia cell differentiation protein Mcl-1 790 nM
790 nM
IC50
IC50
DOI: 10.1039/C5MD00582E
via Super-PRED
CHEMBL1991 O14920 Inhibitor of nuclear factor kappa B kinase beta subunit 3070 nM
IC50
PMID: 22472167
CHEMBL335 P18031 Protein-tyrosine phosphatase 1B 190 nM
Ki
via Super-PRED
CHEMBL2010624 P10599 Thioredoxin 3110 nM
Ki
PMID: 22663155
CHEMBL2189153 Q99757 Thioredoxin, mitochondrial 1310 nM
Ki
PMID: 22663155

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.54% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 96.96% 94.45%
CHEMBL1806 P11388 DNA topoisomerase II alpha 96.85% 89.00%
CHEMBL2581 P07339 Cathepsin D 95.42% 98.95%
CHEMBL284 P27487 Dipeptidyl peptidase IV 94.19% 95.69%
CHEMBL3401 O75469 Pregnane X receptor 92.26% 94.73%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.07% 96.09%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 90.29% 96.38%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.47% 99.23%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.25% 85.14%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.20% 97.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.65% 95.56%
CHEMBL340 P08684 Cytochrome P450 3A4 84.74% 91.19%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.34% 86.33%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 83.14% 96.90%
CHEMBL226 P30542 Adenosine A1 receptor 82.82% 95.93%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.64% 100.00%
CHEMBL1937 Q92769 Histone deacetylase 2 82.25% 94.75%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.69% 96.00%
CHEMBL1293267 Q9HC97 G-protein coupled receptor 35 81.32% 89.34%
CHEMBL3060 Q9Y345 Glycine transporter 2 81.32% 99.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.89% 95.89%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.82% 95.50%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 80.58% 90.71%

Cross-Links

Top
PubChem 9852185
NPASS NPC158329
ChEMBL CHEMBL555017
LOTUS LTS0038445
wikiData Q5519727