(4aR,5S,8aS,9aS)-8a-hydroxy-3,4a,5-trimethyl-5,6,7,8,9,9a-hexahydro-4H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: 060a6ca2-e0b9-463c-99ea-b211689156cb
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4aR,5S,8aS,9aS)-8a-hydroxy-3,4a,5-trimethyl-5,6,7,8,9,9a-hexahydro-4H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1CCCC2(C1(CC3=C(C(=O)OC3C2)C)C)O
• SMILES (Isomeric): C[C@H]1CCC[C@]2([C@@]1(CC3=C(C(=O)O[C@H]3C2)C)C)O
• InChI: InChI=1S/C15H22O3/c1-9-5-4-6-15(17)8-12-11(7-14(9,15)3)10(2)13(16)18-12/h9,12,17H,4-8H2,1-3H3/t9-,12-,14+,15-/m0/s1
• InChI Key: MVFHOCUIRUKOFG-GGZSPTBLSA-N
• Popularity: 1 reference 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: 2.20
• Atomic LogP (AlogP): 2.58
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9972	99.72%
Caco-2	+	0.8355	83.55%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7145	71.45%
OATP2B1 inhibitior	-	0.8521	85.21%
OATP1B1 inhibitior	+	0.9211	92.11%
OATP1B3 inhibitior	+	0.9639	96.39%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	+	0.6750	67.50%
BSEP inhibitior	-	0.8085	80.85%
P-glycoprotein inhibitior	-	0.9017	90.17%
P-glycoprotein substrate	-	0.9077	90.77%
CYP3A4 substrate	+	0.6362	63.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8914	89.14%
CYP3A4 inhibition	-	0.6751	67.51%
CYP2C9 inhibition	-	0.8667	86.67%
CYP2C19 inhibition	-	0.7461	74.61%
CYP2D6 inhibition	-	0.9598	95.98%
CYP1A2 inhibition	-	0.6329	63.29%
CYP2C8 inhibition	-	0.8590	85.90%
CYP inhibitory promiscuity	-	0.9129	91.29%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4468	44.68%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.8376	83.76%
Skin irritation	+	0.6745	67.45%
Skin corrosion	-	0.9149	91.49%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5396	53.96%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5292	52.92%
skin sensitisation	-	0.7618	76.18%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.5651	56.51%
Acute Oral Toxicity (c)	III	0.4125	41.25%
Estrogen receptor binding	-	0.5096	50.96%
Androgen receptor binding	+	0.5237	52.37%
Thyroid receptor binding	+	0.5738	57.38%
Glucocorticoid receptor binding	-	0.5098	50.98%
Aromatase binding	-	0.6133	61.33%
PPAR gamma	-	0.5780	57.80%
Honey bee toxicity	-	0.9290	92.90%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.9885	98.85%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.85%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.87%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.74%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.84%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.24%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.92%	82.69%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	84.52%	86.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.30%	97.14%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.20%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.82%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.69%	85.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.70%	93.04%

Plants that contains it

• Hertia cheirifolia
• Ligularia virgaurea
• Synotis erythropappa

Cross-Links

• PubChem: 14633017
• LOTUS: LTS0055548
• wikiData: Q105172965