(3aS,5R,6R,8aR)-5-hydroxy-6-methyl-3-methylidene-7-(3-oxobutyl)-4,5,6,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one

Details

• Internal ID: e013b1bd-8231-414b-88be-6f2953c63ca2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3aS,5R,6R,8aR)-5-hydroxy-6-methyl-3-methylidene-7-(3-oxobutyl)-4,5,6,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
• SMILES (Canonical): CC1C(CC2C(C=C1CCC(=O)C)OC(=O)C2=C)O
• SMILES (Isomeric): C[C@H]1[C@@H](C[C@@H]2[C@@H](C=C1CCC(=O)C)OC(=O)C2=C)O
• InChI: InChI=1S/C15H20O4/c1-8(16)4-5-11-6-14-12(7-13(17)9(11)2)10(3)15(18)19-14/h6,9,12-14,17H,3-5,7H2,1-2H3/t9-,12+,13-,14-/m1/s1
• InChI Key: RMNBDQLIVSJKBM-GJQVQUKXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 1.78
• H-Bond Acceptor: 4
• 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	+	0.9736	97.36%
Caco-2	+	0.6856	68.56%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5829	58.29%
OATP2B1 inhibitior	-	0.8577	85.77%
OATP1B1 inhibitior	+	0.8320	83.20%
OATP1B3 inhibitior	+	0.9299	92.99%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.8892	88.92%
P-glycoprotein inhibitior	-	0.9019	90.19%
P-glycoprotein substrate	-	0.7249	72.49%
CYP3A4 substrate	+	0.5364	53.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8706	87.06%
CYP3A4 inhibition	-	0.7233	72.33%
CYP2C9 inhibition	-	0.8880	88.80%
CYP2C19 inhibition	-	0.8760	87.60%
CYP2D6 inhibition	-	0.9159	91.59%
CYP1A2 inhibition	-	0.5394	53.94%
CYP2C8 inhibition	-	0.8577	85.77%
CYP inhibitory promiscuity	-	0.9443	94.43%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6690	66.90%
Eye corrosion	-	0.9770	97.70%
Eye irritation	-	0.8710	87.10%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8677	86.77%
Ames mutagenesis	-	0.7164	71.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.6524	65.24%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.8462	84.62%
skin sensitisation	-	0.7081	70.81%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8435	84.35%
Acute Oral Toxicity (c)	III	0.4560	45.60%
Estrogen receptor binding	-	0.6388	63.88%
Androgen receptor binding	-	0.6537	65.37%
Thyroid receptor binding	-	0.6494	64.94%
Glucocorticoid receptor binding	+	0.6228	62.28%
Aromatase binding	-	0.7810	78.10%
PPAR gamma	-	0.6964	69.64%
Honey bee toxicity	-	0.8238	82.38%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9779	97.79%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.58%	83.82%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.89%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.49%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.68%	85.14%
CHEMBL2581	P07339	Cathepsin D	92.57%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.74%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	89.29%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.03%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.21%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.99%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.94%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.60%	94.80%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.12%	95.50%

Plants that contains it

• Euphrosyne dealbata

Cross-Links

• PubChem: 162851674
• LOTUS: LTS0272726
• wikiData: Q105240905