4-hydroxy-6-(3-hydroxypropyl)-5,7-dimethyl-3-methylidene-4,5,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one

Details

• Internal ID: ba9737b1-3684-4410-8138-e8c072285fd2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: 4-hydroxy-6-(3-hydroxypropyl)-5,7-dimethyl-3-methylidene-4,5,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
• SMILES (Canonical): CC1C(C2C(CC(=C1CCCO)C)OC(=O)C2=C)O
• SMILES (Isomeric): CC1C(C2C(CC(=C1CCCO)C)OC(=O)C2=C)O
• InChI: InChI=1S/C15H22O4/c1-8-7-12-13(10(3)15(18)19-12)14(17)9(2)11(8)5-4-6-16/h9,12-14,16-17H,3-7H2,1-2H3
• InChI Key: SAAUSGDGZGFSKS-UHFFFAOYSA-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: 0.90
• Atomic LogP (AlogP): 1.57
• 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	+	0.9792	97.92%
Caco-2	+	0.7064	70.64%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6161	61.61%
OATP2B1 inhibitior	-	0.8532	85.32%
OATP1B1 inhibitior	+	0.8863	88.63%
OATP1B3 inhibitior	+	0.9599	95.99%
MATE1 inhibitior	-	0.9212	92.12%
OCT2 inhibitior	-	0.6781	67.81%
BSEP inhibitior	-	0.9383	93.83%
P-glycoprotein inhibitior	-	0.8735	87.35%
P-glycoprotein substrate	-	0.6898	68.98%
CYP3A4 substrate	+	0.5656	56.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8359	83.59%
CYP3A4 inhibition	-	0.5562	55.62%
CYP2C9 inhibition	-	0.8778	87.78%
CYP2C19 inhibition	-	0.8535	85.35%
CYP2D6 inhibition	-	0.9132	91.32%
CYP1A2 inhibition	-	0.5968	59.68%
CYP2C8 inhibition	-	0.8638	86.38%
CYP inhibitory promiscuity	-	0.9153	91.53%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6833	68.33%
Eye corrosion	-	0.9865	98.65%
Eye irritation	-	0.6890	68.90%
Skin irritation	-	0.6152	61.52%
Skin corrosion	-	0.9427	94.27%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5567	55.67%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.5797	57.97%
skin sensitisation	-	0.8680	86.80%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.7404	74.04%
Acute Oral Toxicity (c)	III	0.3967	39.67%
Estrogen receptor binding	-	0.5728	57.28%
Androgen receptor binding	-	0.5568	55.68%
Thyroid receptor binding	-	0.5339	53.39%
Glucocorticoid receptor binding	+	0.6796	67.96%
Aromatase binding	-	0.6883	68.83%
PPAR gamma	-	0.7245	72.45%
Honey bee toxicity	-	0.8710	87.10%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9757	97.57%

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	90.61%	91.11%
CHEMBL2581	P07339	Cathepsin D	89.75%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.77%	95.56%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	87.65%	96.37%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	87.58%	86.00%
CHEMBL3401	O75469	Pregnane X receptor	86.08%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.68%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.83%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.53%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.03%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.53%	89.00%

Plants that contains it

• Inula japonica

Cross-Links

• PubChem: 46397417
• LOTUS: LTS0104145
• wikiData: Q105248728