(E)-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

Details

• Internal ID: f584f95b-03b3-4c4f-8a53-9d5c66767247
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > Pyranoxanthones
• IUPAC Name: (E)-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-GXSDCXQCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• 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

• gambogic acid
• Cambogic acid
• beta-Guttiferin
• 149655-52-7
• B''-Guttiferin
• GAMBOGICACID
• (E)-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
• 2752-65-0
• CHEBI:67521
• C38H44O8
• C38-H44-O8
• AS-49327

2D Structure

ADMET Properties (via admetSAR 2)

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

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4361	Q07820	Induced myeloid leukemia cell differentiation protein Mcl-1	790 nM	IC50	via Super-PRED
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	190 nM	Ki	via Super-PRED

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%

Plants that contains it

• Callitriche stagnalis
• Croton discolor
• Eclipta prostrata
• Fragaria chiloensis
• Garcinia hanburyi
• Hemionitis glauca
• Millettia extensa
• Rhizomnium pseudopunctatum
• Ruscus hypoglossum
• Salix babylonica
• Scrophularia glabrata
• Toxicodendron radicans
• Vernonanthura discolor
• Wrightia coccinea

Cross-Links

• PubChem: 70697925
• NPASS: NPC53244
• LOTUS: LTS0257800
• wikiData: Q105007429