4-[(1R,3R,4aS,8aS)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]butan-2-one

Details

• Internal ID: 14bf8d01-bca8-40e8-90c9-85fab5ae585a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 4-[(1R,3R,4aS,8aS)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]butan-2-one
• SMILES (Canonical): CC(=O)CCC1C(=C)C(CC2C1(CCCC2(C)C)C)O
• SMILES (Isomeric): CC(=O)CC[C@H]1C(=C)[C@@H](C[C@@H]2[C@@]1(CCCC2(C)C)C)O
• InChI: InChI=1S/C18H30O2/c1-12(19)7-8-14-13(2)15(20)11-16-17(3,4)9-6-10-18(14,16)5/h14-16,20H,2,6-11H2,1,3-5H3/t14-,15+,16-,18+/m0/s1
• InChI Key: ZLALDYHBEJYUAT-UIBIWLFHSA-N
• Popularity: 0 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: 3.50
• Atomic LogP (AlogP): 4.13
• H-Bond Acceptor: 2
• 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	+	0.9973	99.73%
Caco-2	+	0.8080	80.80%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6310	63.10%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.8602	86.02%
OATP1B3 inhibitior	+	0.9247	92.47%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.6781	67.81%
P-glycoprotein inhibitior	-	0.7932	79.32%
P-glycoprotein substrate	-	0.8414	84.14%
CYP3A4 substrate	+	0.5919	59.19%
CYP2C9 substrate	-	0.8495	84.95%
CYP2D6 substrate	-	0.7671	76.71%
CYP3A4 inhibition	-	0.7186	71.86%
CYP2C9 inhibition	-	0.8789	87.89%
CYP2C19 inhibition	-	0.7045	70.45%
CYP2D6 inhibition	-	0.9493	94.93%
CYP1A2 inhibition	-	0.8729	87.29%
CYP2C8 inhibition	-	0.7898	78.98%
CYP inhibitory promiscuity	-	0.7922	79.22%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6555	65.55%
Eye corrosion	-	0.9910	99.10%
Eye irritation	+	0.5420	54.20%
Skin irritation	+	0.6127	61.27%
Skin corrosion	-	0.9643	96.43%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4782	47.82%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.5351	53.51%
skin sensitisation	+	0.6361	63.61%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6251	62.51%
Acute Oral Toxicity (c)	III	0.9056	90.56%
Estrogen receptor binding	+	0.5855	58.55%
Androgen receptor binding	-	0.5754	57.54%
Thyroid receptor binding	+	0.5429	54.29%
Glucocorticoid receptor binding	+	0.6432	64.32%
Aromatase binding	-	0.6141	61.41%
PPAR gamma	-	0.5704	57.04%
Honey bee toxicity	-	0.8086	80.86%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9927	99.27%

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	94.36%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	93.82%	82.69%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.87%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.38%	96.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.16%	96.38%
CHEMBL2581	P07339	Cathepsin D	89.18%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	88.08%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.47%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.87%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.30%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.44%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	80.82%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.47%	100.00%

Plants that contains it

• Aristeguietia salvia

Cross-Links

• PubChem: 162878409
• LOTUS: LTS0191350
• wikiData: Q105378830