(3S,3aS,5S,6S,7S,7aS)-6-ethenyl-5-hydroxy-3,6-dimethyl-7-prop-1-en-2-yl-3,3a,4,5,7,7a-hexahydro-1-benzofuran-2-one

Details

• Internal ID: d15be1a1-b69c-4402-8e0b-21ea09cf9d66
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (3S,3aS,5S,6S,7S,7aS)-6-ethenyl-5-hydroxy-3,6-dimethyl-7-prop-1-en-2-yl-3,3a,4,5,7,7a-hexahydro-1-benzofuran-2-one
• SMILES (Canonical): CC1C2CC(C(C(C2OC1=O)C(=C)C)(C)C=C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2C[C@@H]([C@@]([C@@H]([C@H]2OC1=O)C(=C)C)(C)C=C)O
• InChI: InChI=1S/C15H22O3/c1-6-15(5)11(16)7-10-9(4)14(17)18-13(10)12(15)8(2)3/h6,9-13,16H,1-2,7H2,3-5H3/t9-,10-,11-,12+,13-,15+/m0/s1
• InChI Key: CJANUBPCKSSOSU-QBOXMOKDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 2.31
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9969	99.69%
Caco-2	-	0.6598	65.98%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5635	56.35%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.9252	92.52%
OATP1B3 inhibitior	+	0.9406	94.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9818	98.18%
P-glycoprotein inhibitior	-	0.9317	93.17%
P-glycoprotein substrate	-	0.8019	80.19%
CYP3A4 substrate	+	0.5594	55.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8395	83.95%
CYP3A4 inhibition	-	0.7616	76.16%
CYP2C9 inhibition	-	0.9701	97.01%
CYP2C19 inhibition	-	0.9225	92.25%
CYP2D6 inhibition	-	0.9569	95.69%
CYP1A2 inhibition	-	0.7753	77.53%
CYP2C8 inhibition	-	0.9397	93.97%
CYP inhibitory promiscuity	-	0.9043	90.43%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9217	92.17%
Carcinogenicity (trinary)	Non-required	0.5198	51.98%
Eye corrosion	-	0.9600	96.00%
Eye irritation	-	0.5935	59.35%
Skin irritation	+	0.6262	62.62%
Skin corrosion	-	0.8461	84.61%
Ames mutagenesis	+	0.5146	51.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.5455	54.55%
Micronuclear	-	0.6741	67.41%
Hepatotoxicity	+	0.7283	72.83%
skin sensitisation	+	0.5922	59.22%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.7459	74.59%
Acute Oral Toxicity (c)	III	0.6248	62.48%
Estrogen receptor binding	+	0.6471	64.71%
Androgen receptor binding	+	0.5482	54.82%
Thyroid receptor binding	-	0.5354	53.54%
Glucocorticoid receptor binding	-	0.4677	46.77%
Aromatase binding	-	0.7478	74.78%
PPAR gamma	-	0.7204	72.04%
Honey bee toxicity	-	0.5915	59.15%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9193	91.93%

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	97.38%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.30%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.43%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.08%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.83%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.91%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.55%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.80%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.16%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	80.53%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.23%	99.23%

Plants that contains it

• Seriphidium fragrans

Cross-Links

• PubChem: 162984261
• LOTUS: LTS0215037
• wikiData: Q104960729