(2S,4R,4aS,8aR)-4a,8,8-trimethyl-3-methylidene-4-[(2E)-3-methylpenta-2,4-dienyl]-2,4,5,6,7,8a-hexahydro-1H-naphthalen-2-ol

Details

• Internal ID: 3304bb41-fc61-4ad2-a89e-182a7d187ebe
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (2S,4R,4aS,8aR)-4a,8,8-trimethyl-3-methylidene-4-[(2E)-3-methylpenta-2,4-dienyl]-2,4,5,6,7,8a-hexahydro-1H-naphthalen-2-ol
• SMILES (Canonical): CC(=CCC1C(=C)C(CC2C1(CCCC2(C)C)C)O)C=C
• SMILES (Isomeric): C/C(=C\C[C@H]1C(=C)[C@H](C[C@H]2[C@@]1(CCCC2(C)C)C)O)/C=C
• InChI: InChI=1S/C20H32O/c1-7-14(2)9-10-16-15(3)17(21)13-18-19(4,5)11-8-12-20(16,18)6/h7,9,16-18,21H,1,3,8,10-13H2,2,4-6H3/b14-9+/t16-,17-,18+,20+/m0/s1
• InChI Key: UITXFWAOWQMNFN-FFDAWANBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O
• Molecular Weight: 288.50 g/mol
• Exact Mass: 288.245315640 g/mol
• Topological Polar Surface Area (TPSA): 20.20 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 5.28
• H-Bond Acceptor: 1
• 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	+	0.9952	99.52%
Caco-2	+	0.7518	75.18%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Lysosomes	0.5691	56.91%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.8442	84.42%
OATP1B3 inhibitior	+	0.8846	88.46%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6190	61.90%
P-glycoprotein inhibitior	-	0.8520	85.20%
P-glycoprotein substrate	-	0.7546	75.46%
CYP3A4 substrate	+	0.6148	61.48%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7337	73.37%
CYP3A4 inhibition	-	0.7309	73.09%
CYP2C9 inhibition	-	0.8506	85.06%
CYP2C19 inhibition	-	0.7237	72.37%
CYP2D6 inhibition	-	0.9485	94.85%
CYP1A2 inhibition	-	0.8619	86.19%
CYP2C8 inhibition	-	0.6101	61.01%
CYP inhibitory promiscuity	-	0.6913	69.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6775	67.75%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.8668	86.68%
Skin irritation	+	0.6083	60.83%
Skin corrosion	-	0.9411	94.11%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8501	85.01%
Micronuclear	-	0.9800	98.00%
Hepatotoxicity	-	0.5048	50.48%
skin sensitisation	+	0.6968	69.68%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.5833	58.33%
Acute Oral Toxicity (c)	III	0.9027	90.27%
Estrogen receptor binding	+	0.6136	61.36%
Androgen receptor binding	-	0.5062	50.62%
Thyroid receptor binding	-	0.4928	49.28%
Glucocorticoid receptor binding	+	0.5868	58.68%
Aromatase binding	-	0.5209	52.09%
PPAR gamma	+	0.6608	66.08%
Honey bee toxicity	-	0.7714	77.14%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9922	99.22%

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	95.91%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.40%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	91.32%	94.75%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	89.71%	82.69%
CHEMBL1977	P11473	Vitamin D receptor	87.01%	99.43%
CHEMBL221	P23219	Cyclooxygenase-1	86.51%	90.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.44%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.02%	96.09%
CHEMBL2581	P07339	Cathepsin D	83.64%	98.95%
CHEMBL233	P35372	Mu opioid receptor	82.92%	97.93%

Plants that contains it

• Nicotiana raimondii

Cross-Links

• PubChem: 163095284
• LOTUS: LTS0142801
• wikiData: Q105273577