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

Details

• Internal ID: 5249b635-22cd-490b-a905-bffbafa5c40a
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (5aR,6S,7S,9aS,9bR)-7-hydroxy-6-(hydroxymethyl)-6,9a-dimethyl-5,5a,7,8,9,9b-hexahydro-1H-benzo[e][2]benzofuran-3-one
• SMILES (Canonical): CC12CCC(C(C1CC=C3C2COC3=O)(C)CO)O
• SMILES (Isomeric): C[C@]12CC[C@@H]([C@]([C@@H]1CC=C3[C@@H]2COC3=O)(C)CO)O
• InChI: InChI=1S/C15H22O4/c1-14-6-5-12(17)15(2,8-16)11(14)4-3-9-10(14)7-19-13(9)18/h3,10-12,16-17H,4-8H2,1-2H3/t10-,11+,12-,14+,15+/m0/s1
• InChI Key: KGNKJLSLHCPWOB-SZWZKDINSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.27
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9700	97.00%
Caco-2	+	0.8211	82.11%
Blood Brain Barrier	+	0.5763	57.63%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7621	76.21%
OATP2B1 inhibitior	-	0.8538	85.38%
OATP1B1 inhibitior	+	0.9300	93.00%
OATP1B3 inhibitior	+	0.9453	94.53%
MATE1 inhibitior	-	0.8212	82.12%
OCT2 inhibitior	+	0.5662	56.62%
BSEP inhibitior	-	0.6663	66.63%
P-glycoprotein inhibitior	-	0.9401	94.01%
P-glycoprotein substrate	-	0.8038	80.38%
CYP3A4 substrate	+	0.6318	63.18%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.8794	87.94%
CYP3A4 inhibition	-	0.7979	79.79%
CYP2C9 inhibition	-	0.9284	92.84%
CYP2C19 inhibition	-	0.9217	92.17%
CYP2D6 inhibition	-	0.9276	92.76%
CYP1A2 inhibition	-	0.8957	89.57%
CYP2C8 inhibition	-	0.9030	90.30%
CYP inhibitory promiscuity	-	0.8716	87.16%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5199	51.99%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.8426	84.26%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.7370	73.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.5780	57.80%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.6165	61.65%
skin sensitisation	-	0.9113	91.13%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.5269	52.69%
Acute Oral Toxicity (c)	III	0.6161	61.61%
Estrogen receptor binding	+	0.5294	52.94%
Androgen receptor binding	+	0.7254	72.54%
Thyroid receptor binding	+	0.5478	54.78%
Glucocorticoid receptor binding	+	0.5543	55.43%
Aromatase binding	-	0.6026	60.26%
PPAR gamma	-	0.4908	49.08%
Honey bee toxicity	-	0.8944	89.44%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9737	97.37%

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	95.82%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	93.17%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.57%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.89%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.29%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.36%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.33%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.46%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	85.73%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.81%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.90%	95.89%

Plants that contains it

• Iresine diffusa

Cross-Links

• PubChem: 163074387
• LOTUS: LTS0157825
• wikiData: Q105140865