3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]furan-2-one

Details

• Internal ID: 03c6c5d3-f1a5-48fe-85df-689d830a0f91
• Taxonomy: Organoheterocyclic compounds > Dihydrofurans > Furanones > Butenolides
• IUPAC Name: 3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]furan-2-one
• SMILES (Canonical): CC12CCC(C(C1CCC(=C)C2CC=C3C=COC3=O)(C)CO)O
• SMILES (Isomeric): C[C@@]12CC[C@H]([C@@]([C@H]1CCC(=C)[C@H]2CC=C3C=COC3=O)(C)CO)O
• InChI: InChI=1S/C20H28O4/c1-13-4-7-16-19(2,10-8-17(22)20(16,3)12-21)15(13)6-5-14-9-11-24-18(14)23/h5,9,11,15-17,21-22H,1,4,6-8,10,12H2,2-3H3/t15-,16+,17-,19+,20+/m1/s1
• InChI Key: YIIRVUDGRKEWBV-YSDSKTICSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.12
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9712	97.12%
Caco-2	+	0.6299	62.99%
Blood Brain Barrier	+	0.5777	57.77%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.6820	68.20%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9165	91.65%
OATP1B3 inhibitior	+	0.9400	94.00%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.5381	53.81%
BSEP inhibitior	+	0.6384	63.84%
P-glycoprotein inhibitior	-	0.8127	81.27%
P-glycoprotein substrate	-	0.7704	77.04%
CYP3A4 substrate	+	0.6950	69.50%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8781	87.81%
CYP3A4 inhibition	-	0.6598	65.98%
CYP2C9 inhibition	-	0.9001	90.01%
CYP2C19 inhibition	-	0.9135	91.35%
CYP2D6 inhibition	-	0.9350	93.50%
CYP1A2 inhibition	-	0.8782	87.82%
CYP2C8 inhibition	-	0.7234	72.34%
CYP inhibitory promiscuity	-	0.8360	83.60%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6138	61.38%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.9380	93.80%
Skin irritation	+	0.5462	54.62%
Skin corrosion	-	0.9376	93.76%
Ames mutagenesis	-	0.7370	73.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8067	80.67%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.8861	88.61%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.6376	63.76%
Acute Oral Toxicity (c)	III	0.4636	46.36%
Estrogen receptor binding	+	0.6903	69.03%
Androgen receptor binding	+	0.7150	71.50%
Thyroid receptor binding	+	0.6522	65.22%
Glucocorticoid receptor binding	+	0.7000	70.00%
Aromatase binding	+	0.7185	71.85%
PPAR gamma	-	0.5904	59.04%
Honey bee toxicity	-	0.8599	85.99%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9884	98.84%

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	94.42%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.73%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.43%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.99%	100.00%
CHEMBL2581	P07339	Cathepsin D	89.59%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.24%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.56%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.25%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.62%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.12%	94.45%
CHEMBL5028	O14672	ADAM10	80.66%	97.50%
CHEMBL4040	P28482	MAP kinase ERK2	80.34%	83.82%

Plants that contains it

• Andrographis paniculata

Cross-Links

• PubChem: 452936
• LOTUS: LTS0049783
• wikiData: Q105348860