Isogambogenic acid

Details

• Internal ID: e3654597-ac02-4881-a0f7-4025084ad51f
• Taxonomy: Organoheterocyclic compounds > Benzopyrans > 1-benzopyrans > Xanthones
• IUPAC Name: (E)-4-[(1S,2S,13S,15R)-7-[(2E)-3,7-dimethylocta-2,6-dienyl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-enyl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid
• SMILES (Canonical): CC(=CCCC(=CCC1=C(C(=C2C(=C1O)C(=O)C3=CC4CC5C3(O2)C(C4=O)(OC5(C)C)CC=C(C)C(=O)O)CC=C(C)C)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC1=C(C(=C2C(=C1O)C(=O)C3=C[C@@H]4C[C@@H]5[C@@]3(O2)[C@](C4=O)(OC5(C)C)C/C=C(\C)/C(=O)O)CC=C(C)C)O)/C)C
• InChI: InChI=1S/C38H46O8/c1-20(2)10-9-11-22(5)13-15-25-30(39)26(14-12-21(3)4)33-29(31(25)40)32(41)27-18-24-19-28-36(7,8)46-37(34(24)42,38(27,28)45-33)17-16-23(6)35(43)44/h10,12-13,16,18,24,28,39-40H,9,11,14-15,17,19H2,1-8H3,(H,43,44)/b22-13+,23-16+/t24-,28+,37+,38-/m1/s1
• InChI Key: RCWNBHCZYXWDOV-SDNKGDDVSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₄₆O₈
• Molecular Weight: 630.80 g/mol
• Exact Mass: 630.31926842 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 7.90
• Atomic LogP (AlogP): 7.27
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 10

Synonyms

• (E)-4-[(1S,2S,13S,15R)-7-[(2E)-3,7-Dimethylocta-2,6-dienyl]-6,8-dihydroxy-17,17-dimethyl-5-(3-methylbut-2-enyl)-10,14-dioxo-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraen-15-yl]-2-methylbut-2-enoic acid
• Gambogenic Acid
• 887923-47-9
• CHEMBL4584357
• 173932-75-7
• HY-122948
• CS-0090638

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9702	97.02%
Caco-2	-	0.8025	80.25%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7790	77.90%
OATP2B1 inhibitior	+	0.5668	56.68%
OATP1B1 inhibitior	+	0.6847	68.47%
OATP1B3 inhibitior	-	0.3859	38.59%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	+	0.9971	99.71%
P-glycoprotein inhibitior	+	0.8259	82.59%
P-glycoprotein substrate	-	0.5134	51.34%
CYP3A4 substrate	+	0.6889	68.89%
CYP2C9 substrate	+	0.6017	60.17%
CYP2D6 substrate	-	0.8673	86.73%
CYP3A4 inhibition	-	0.7548	75.48%
CYP2C9 inhibition	-	0.6141	61.41%
CYP2C19 inhibition	-	0.7153	71.53%
CYP2D6 inhibition	-	0.9057	90.57%
CYP1A2 inhibition	-	0.5309	53.09%
CYP2C8 inhibition	+	0.7205	72.05%
CYP inhibitory promiscuity	-	0.7278	72.78%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5094	50.94%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.8949	89.49%
Skin irritation	-	0.6076	60.76%
Skin corrosion	-	0.9165	91.65%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4267	42.67%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.7250	72.50%
skin sensitisation	-	0.8329	83.29%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	-	0.8728	87.28%
Acute Oral Toxicity (c)	I	0.3753	37.53%
Estrogen receptor binding	+	0.8138	81.38%
Androgen receptor binding	+	0.7662	76.62%
Thyroid receptor binding	+	0.6445	64.45%
Glucocorticoid receptor binding	+	0.8366	83.66%
Aromatase binding	+	0.7586	75.86%
PPAR gamma	+	0.6941	69.41%
Honey bee toxicity	-	0.7199	71.99%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.65%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.29%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.97%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.33%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.56%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.79%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	89.47%	94.73%
CHEMBL284	P27487	Dipeptidyl peptidase IV	87.17%	95.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.09%	97.09%
CHEMBL221	P23219	Cyclooxygenase-1	84.98%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.73%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	84.29%	91.19%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.78%	95.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.76%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.03%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.70%	100.00%

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: 101389903
• NPASS: NPC176240
• LOTUS: LTS0124571
• wikiData: Q104400273