(E)-4-[(1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]but-3-en-2-one

Details

• Internal ID: 3924e0a4-1bed-44c4-9a6e-f911f863d364
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (E)-4-[(1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]but-3-en-2-one
• SMILES (Canonical): CC(=O)C=CC1C2(CCCC(C2CCC1(C)O)(C)C)C
• SMILES (Isomeric): CC(=O)/C=C/[C@@H]1[C@]2(CCCC([C@@H]2CC[C@@]1(C)O)(C)C)C
• InChI: InChI=1S/C18H30O2/c1-13(19)7-8-15-17(4)11-6-10-16(2,3)14(17)9-12-18(15,5)20/h7-8,14-15,20H,6,9-12H2,1-5H3/b8-7+/t14-,15+,17-,18+/m0/s1
• InChI Key: SNUHZNCSBAQVJV-JIDYTCFASA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₀O₂
• Molecular Weight: 278.40 g/mol
• Exact Mass: 278.224580195 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 4.13
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• SCHEMBL20640825

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.7533	75.33%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7424	74.24%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.9263	92.63%
OATP1B3 inhibitior	+	0.9765	97.65%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	-	0.6610	66.10%
P-glycoprotein inhibitior	-	0.9001	90.01%
P-glycoprotein substrate	-	0.9180	91.80%
CYP3A4 substrate	+	0.5965	59.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9031	90.31%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8322	83.22%
CYP2C19 inhibition	-	0.6996	69.96%
CYP2D6 inhibition	-	0.9639	96.39%
CYP1A2 inhibition	-	0.7190	71.90%
CYP2C8 inhibition	-	0.7938	79.38%
CYP inhibitory promiscuity	-	0.9362	93.62%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6227	62.27%
Eye corrosion	-	0.9844	98.44%
Eye irritation	-	0.9100	91.00%
Skin irritation	+	0.6731	67.31%
Skin corrosion	-	0.9586	95.86%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5627	56.27%
Micronuclear	-	1.0000	100.00%
Hepatotoxicity	-	0.6315	63.15%
skin sensitisation	+	0.6338	63.38%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5185	51.85%
Acute Oral Toxicity (c)	III	0.8050	80.50%
Estrogen receptor binding	+	0.6224	62.24%
Androgen receptor binding	-	0.6650	66.50%
Thyroid receptor binding	+	0.6962	69.62%
Glucocorticoid receptor binding	+	0.6819	68.19%
Aromatase binding	-	0.6284	62.84%
PPAR gamma	-	0.5618	56.18%
Honey bee toxicity	-	0.8662	86.62%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9814	98.14%

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	96.80%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.38%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.02%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	86.74%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.12%	100.00%
CHEMBL4370	P16662	UDP-glucuronosyltransferase 2B7	85.71%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.90%	95.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.27%	92.94%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.23%	82.69%
CHEMBL5255	O00206	Toll-like receptor 4	80.58%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.39%	91.24%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.38%	96.38%

Plants that contains it

• Lindheimera texana

Cross-Links

• PubChem: 11892087
• LOTUS: LTS0138004
• wikiData: Q105256685