(5aS,6S,7S,9aS,9bR)-7-hydroxy-6,9a-dimethyl-6-(4-methylpent-3-enyl)-5,5a,7,8,9,9b-hexahydro-1H-benzo[e][2]benzofuran-3-one

Details

• Internal ID: 2220ff50-88c6-425e-b3ba-bdceb9594878
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (5aS,6S,7S,9aS,9bR)-7-hydroxy-6,9a-dimethyl-6-(4-methylpent-3-enyl)-5,5a,7,8,9,9b-hexahydro-1H-benzo[e][2]benzofuran-3-one
• SMILES (Canonical): CC(=CCCC1(C(CCC2(C1CC=C3C2COC3=O)C)O)C)C
• SMILES (Isomeric): CC(=CCC[C@@]1([C@H](CC[C@]2([C@@H]1CC=C3[C@@H]2COC3=O)C)O)C)C
• InChI: InChI=1S/C20H30O3/c1-13(2)6-5-10-20(4)16-8-7-14-15(12-23-18(14)22)19(16,3)11-9-17(20)21/h6-7,15-17,21H,5,8-12H2,1-4H3/t15-,16-,17-,19+,20-/m0/s1
• InChI Key: VYTCTWUSWTXAEI-CAVMOMJPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₃
• Molecular Weight: 318.40 g/mol
• Exact Mass: 318.21949481 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.02
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9970	99.70%
Caco-2	+	0.8173	81.73%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8566	85.66%
OATP2B1 inhibitior	-	0.8654	86.54%
OATP1B1 inhibitior	+	0.9025	90.25%
OATP1B3 inhibitior	+	0.9729	97.29%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	+	0.8775	87.75%
P-glycoprotein inhibitior	-	0.6885	68.85%
P-glycoprotein substrate	-	0.7637	76.37%
CYP3A4 substrate	+	0.6511	65.11%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8757	87.57%
CYP3A4 inhibition	-	0.6042	60.42%
CYP2C9 inhibition	-	0.7660	76.60%
CYP2C19 inhibition	-	0.7917	79.17%
CYP2D6 inhibition	-	0.9246	92.46%
CYP1A2 inhibition	-	0.8661	86.61%
CYP2C8 inhibition	-	0.8346	83.46%
CYP inhibitory promiscuity	-	0.7880	78.80%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5726	57.26%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.8130	81.30%
Skin irritation	+	0.5174	51.74%
Skin corrosion	-	0.9435	94.35%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4103	41.03%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.5600	56.00%
skin sensitisation	-	0.7734	77.34%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.4945	49.45%
Acute Oral Toxicity (c)	III	0.6521	65.21%
Estrogen receptor binding	+	0.7564	75.64%
Androgen receptor binding	+	0.6408	64.08%
Thyroid receptor binding	+	0.6433	64.33%
Glucocorticoid receptor binding	+	0.7354	73.54%
Aromatase binding	+	0.5361	53.61%
PPAR gamma	+	0.7189	71.89%
Honey bee toxicity	-	0.8283	82.83%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9919	99.19%

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	97.51%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.81%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.95%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.34%	100.00%
CHEMBL1937	Q92769	Histone deacetylase 2	90.16%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.96%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.81%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	87.62%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.80%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.42%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.56%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.84%	95.89%

Plants that contains it

• Pellia endiviifolia

Cross-Links

• PubChem: 162875684
• LOTUS: LTS0112395
• wikiData: Q105299318