Istanbulin A

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	2a0a0783-681c-4ec1-bf9f-f9d3cc98dc4e
Taxonomy	Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
IUPAC Name	(4aS,5R,8aR,9aS)-9a-hydroxy-3,4a,5-trimethyl-4,5,6,7,8a,9-hexahydrobenzo[f][1]benzofuran-2,8-dione
SMILES (Canonical)	CC1CCC(=O)C2C1(CC3=C(C(=O)OC3(C2)O)C)C
SMILES (Isomeric)	C[C@@H]1CCC(=O)[C@H]2[C@]1(CC3=C(C(=O)O[C@]3(C2)O)C)C
InChI	InChI=1S/C15H20O4/c1-8-4-5-12(16)11-7-15(18)10(6-14(8,11)3)9(2)13(17)19-15/h8,11,18H,4-7H2,1-3H3/t8-,11+,14+,15+/m1/s1
InChI Key	HYBIDSYXKTYHCM-BXLXJPJESA-N
Popularity	15 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₅H₂₀O₄
Molecular Weight	264.32 g/mol
Exact Mass	264.13615911 g/mol
Topological Polar Surface Area (TPSA)	63.60 Å²
XlogP	1.10
Atomic LogP (AlogP)	1.96
H-Bond Acceptor	4
H-Bond Donor	1
Rotatable Bonds	0

Synonyms

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Istanbulin-A

35481-83-5

(4aS,5R,8aR,9aS)-9a-hydroxy-3,4a,5-trimethyl-4,5,6,7,8a,9-hexahydrobenzo[f][1]benzofuran-2,8-dione

Naphtho(2,3-b)furan-2,8(4H,5H)-dione, 4a,6,7,8a,9,9a-hexahydro-9a-hydroxy-3,4a,5-trimethyl-, (4aS-(4aalpha,5alpha,8abeta,9abeta))-

(-)-Istanbulin A

DTXSID90956885

CHEBI:174481

(4aS,5R,8aR,9aS)-9a-hydroxy-3,4a,5-trimethyl-4,5,6,7,8a,9-hexahydrobenzo[][1]benzouran-2,8-dione

9a-hydroxy-3,4a,5-trimethyl-4a,6,7,8a,9,9a-hexahydro-4H,5H- naphtho[2,3-b]furan-2,8-dione

9a-Hydroxy-3,4a,5-trimethyl-4a,6,7,8a,9,9a-hexahydronaphtho[2,3-b]furan-2,8(4H,5H)-dione

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9959	99.59%
Caco-2	+	0.8920	89.20%
Blood Brain Barrier	+	0.7750	77.50%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7738	77.38%
OATP2B1 inhibitior	-	0.8529	85.29%
OATP1B1 inhibitior	+	0.9182	91.82%
OATP1B3 inhibitior	+	0.9197	91.97%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.5553	55.53%
BSEP inhibitior	-	0.8408	84.08%
P-glycoprotein inhibitior	-	0.8988	89.88%
P-glycoprotein substrate	-	0.8523	85.23%
CYP3A4 substrate	+	0.6021	60.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8883	88.83%
CYP3A4 inhibition	-	0.6740	67.40%
CYP2C9 inhibition	-	0.8981	89.81%
CYP2C19 inhibition	-	0.9528	95.28%
CYP2D6 inhibition	-	0.9701	97.01%
CYP1A2 inhibition	-	0.7637	76.37%
CYP2C8 inhibition	-	0.9269	92.69%
CYP inhibitory promiscuity	-	0.9713	97.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5047	50.47%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.7942	79.42%
Skin irritation	+	0.6806	68.06%
Skin corrosion	-	0.8845	88.45%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5216	52.16%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8066	80.66%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.5809	58.09%
Acute Oral Toxicity (c)	I	0.3148	31.48%
Estrogen receptor binding	-	0.7722	77.22%
Androgen receptor binding	+	0.5332	53.32%
Thyroid receptor binding	+	0.6072	60.72%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	-	0.6911	69.11%
PPAR gamma	-	0.6384	63.84%
Honey bee toxicity	-	0.8509	85.09%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9926	99.26%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
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	95.00%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.97%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.18%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.09%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.54%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.41%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.93%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.92%	96.09%
CHEMBL1871	P10275	Androgen Receptor	85.12%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.99%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.21%	92.94%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.28%	97.14%
CHEMBL1902	P62942	FK506-binding protein 1A	81.24%	97.05%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.