Gambogoic acid A

Details

• Internal ID: a0e76586-c01f-415a-89c7-a79d72b9af67
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones > Pyranoxanthones
• IUPAC Name: (Z)-4-[(1S,2S,8R,15S,16S,17S,19R)-12-hydroxy-16-methoxy-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-tetraen-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)OC)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@@H]([C@@H]4C3=O)OC)C(=O)[C@@]5(OC6(C)C)C/C=C(/C)\C(=O)O)O)C)C
• InChI: InChI=1S/C39H48O9/c1-20(2)11-10-16-37(8)17-15-23-29(40)27-30(41)28-33(45-9)25-19-26-36(6,7)48-38(34(25)42,18-14-22(5)35(43)44)39(26,28)47-32(27)24(31(23)46-37)13-12-21(3)4/h11-12,14-15,17,25-26,28,33,40H,10,13,16,18-19H2,1-9H3,(H,43,44)/b22-14-/t25-,26-,28-,33-,37+,38-,39-/m0/s1
• InChI Key: WRIWCDIPAFGNEY-AFXVHKFFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₄₈O₉
• Molecular Weight: 660.80 g/mol
• Exact Mass: 660.32983310 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 6.90
• Atomic LogP (AlogP): 6.94
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• EX-A6188
• (Z)-2-Methyl-4-[(1R,14aS)-3,3,11-trimethyl-6alpha-methoxy-7,15-dioxo-8-hydroxy-11beta-(4-methyl-3-pentenyl)-13-(3-methyl-2-butenyl)-1alpha,5alpha-methano-3abeta,4,5,6,6abeta,7-hexahydro-3H,11H-furo[3,4-g]pyrano[3,2-b]xanthene-1-yl]-2-butenoic acid
• 887923-49-1

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9648	96.48%
Caco-2	-	0.8071	80.71%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7678	76.78%
OATP2B1 inhibitior	-	0.5739	57.39%
OATP1B1 inhibitior	-	0.5263	52.63%
OATP1B3 inhibitior	-	0.2448	24.48%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9968	99.68%
P-glycoprotein inhibitior	+	0.8341	83.41%
P-glycoprotein substrate	+	0.6405	64.05%
CYP3A4 substrate	+	0.7135	71.35%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8689	86.89%
CYP3A4 inhibition	-	0.7800	78.00%
CYP2C9 inhibition	-	0.6075	60.75%
CYP2C19 inhibition	-	0.5851	58.51%
CYP2D6 inhibition	-	0.8608	86.08%
CYP1A2 inhibition	-	0.5201	52.01%
CYP2C8 inhibition	+	0.7596	75.96%
CYP inhibitory promiscuity	-	0.6388	63.88%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4785	47.85%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9085	90.85%
Skin irritation	-	0.6903	69.03%
Skin corrosion	-	0.9211	92.11%
Ames mutagenesis	-	0.6237	62.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3770	37.70%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8219	82.19%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.9214	92.14%
Acute Oral Toxicity (c)	I	0.5599	55.99%
Estrogen receptor binding	+	0.8253	82.53%
Androgen receptor binding	+	0.7732	77.32%
Thyroid receptor binding	+	0.6334	63.34%
Glucocorticoid receptor binding	+	0.8507	85.07%
Aromatase binding	+	0.7529	75.29%
PPAR gamma	+	0.7527	75.27%
Honey bee toxicity	-	0.7007	70.07%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9916	99.16%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	300 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	99.72%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.21%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.39%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.35%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.08%	97.09%
CHEMBL2581	P07339	Cathepsin D	92.45%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.76%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.23%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.66%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	89.86%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.86%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.35%	95.89%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.00%	89.34%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.99%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.93%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.28%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	86.17%	96.00%
CHEMBL1929	P47989	Xanthine dehydrogenase	85.94%	96.12%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.75%	97.28%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	83.79%	85.30%
CHEMBL1937	Q92769	Histone deacetylase 2	82.84%	94.75%
CHEMBL1951	P21397	Monoamine oxidase A	80.86%	91.49%
CHEMBL284	P27487	Dipeptidyl peptidase IV	80.29%	95.69%

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: 101377134
• NPASS: NPC280547
• LOTUS: LTS0240864
• wikiData: Q105311330