(4aR,8R,8aS)-8-[(E)-5-hydroxy-3-methylpent-3-enyl]-4,4,7,8a-tetramethyl-3,4a,5,8-tetrahydro-1H-naphthalen-2-one

Details

• Internal ID: bdac16a6-275e-45bc-9ca6-7f1408a9219c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (4aR,8R,8aS)-8-[(E)-5-hydroxy-3-methylpent-3-enyl]-4,4,7,8a-tetramethyl-3,4a,5,8-tetrahydro-1H-naphthalen-2-one
• SMILES (Canonical): CC1=CCC2C(CC(=O)CC2(C1CCC(=CCO)C)C)(C)C
• SMILES (Isomeric): CC1=CC[C@H]2[C@@]([C@@H]1CC/C(=C/CO)/C)(CC(=O)CC2(C)C)C
• InChI: InChI=1S/C20H32O2/c1-14(10-11-21)6-8-17-15(2)7-9-18-19(3,4)12-16(22)13-20(17,18)5/h7,10,17-18,21H,6,8-9,11-13H2,1-5H3/b14-10+/t17-,18-,20-/m1/s1
• InChI Key: SQQMOIGHDIGSOT-IKXMNWQYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₂
• Molecular Weight: 304.50 g/mol
• Exact Mass: 304.240230259 g/mol
• Topological Polar Surface Area (TPSA): 37.30 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.68
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	+	0.8150	81.50%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7340	73.40%
OATP2B1 inhibitior	-	0.8597	85.97%
OATP1B1 inhibitior	+	0.9005	90.05%
OATP1B3 inhibitior	+	0.9104	91.04%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5936	59.36%
BSEP inhibitior	+	0.6453	64.53%
P-glycoprotein inhibitior	-	0.6559	65.59%
P-glycoprotein substrate	-	0.8410	84.10%
CYP3A4 substrate	+	0.5979	59.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8045	80.45%
CYP3A4 inhibition	-	0.8089	80.89%
CYP2C9 inhibition	-	0.8066	80.66%
CYP2C19 inhibition	-	0.7328	73.28%
CYP2D6 inhibition	-	0.9184	91.84%
CYP1A2 inhibition	-	0.7681	76.81%
CYP2C8 inhibition	-	0.7140	71.40%
CYP inhibitory promiscuity	-	0.7512	75.12%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6212	62.12%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9035	90.35%
Skin irritation	-	0.5634	56.34%
Skin corrosion	-	0.9771	97.71%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7661	76.61%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.6446	64.46%
skin sensitisation	-	0.5347	53.47%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.5211	52.11%
Acute Oral Toxicity (c)	III	0.8666	86.66%
Estrogen receptor binding	+	0.6136	61.36%
Androgen receptor binding	-	0.6322	63.22%
Thyroid receptor binding	+	0.5427	54.27%
Glucocorticoid receptor binding	+	0.6358	63.58%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.6035	60.35%
Honey bee toxicity	-	0.8999	89.99%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9766	97.66%

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	95.82%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.19%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.67%	97.25%
CHEMBL2581	P07339	Cathepsin D	89.25%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	88.40%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.11%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.09%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.21%	96.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.69%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.57%	97.09%
CHEMBL4040	P28482	MAP kinase ERK2	81.71%	83.82%
CHEMBL1871	P10275	Androgen Receptor	81.21%	96.43%

Plants that contains it

• Baccharis gnidiifolia

Cross-Links

• PubChem: 163106020
• LOTUS: LTS0198412
• wikiData: Q105258396