(3S,4aS,8R,8aS)-3-hydroxy-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: 5ee97dac-f9af-4677-a6d0-73942f44ed83
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: (3S,4aS,8R,8aS)-3-hydroxy-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(C(C(=O)CC2(C1CCC(=CCO)C)C)O)(C)C
• SMILES (Isomeric): CC1=CC[C@H]2[C@]([C@@H]1CC/C(=C/CO)/C)(CC(=O)[C@H](C2(C)C)O)C
• InChI: InChI=1S/C20H32O3/c1-13(10-11-21)6-8-15-14(2)7-9-17-19(3,4)18(23)16(22)12-20(15,17)5/h7,10,15,17-18,21,23H,6,8-9,11-12H2,1-5H3/b13-10+/t15-,17-,18-,20+/m1/s1
• InChI Key: RMFOHDNAEOCEQV-OXXHCNNESA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.50 g/mol
• Exact Mass: 320.23514488 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.65
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9951	99.51%
Caco-2	+	0.7195	71.95%
Blood Brain Barrier	+	0.6885	68.85%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8756	87.56%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.8988	89.88%
OATP1B3 inhibitior	+	0.9285	92.85%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6302	63.02%
BSEP inhibitior	+	0.6891	68.91%
P-glycoprotein inhibitior	-	0.7580	75.80%
P-glycoprotein substrate	-	0.7912	79.12%
CYP3A4 substrate	+	0.6193	61.93%
CYP2C9 substrate	-	0.8407	84.07%
CYP2D6 substrate	-	0.7921	79.21%
CYP3A4 inhibition	-	0.7343	73.43%
CYP2C9 inhibition	-	0.7544	75.44%
CYP2C19 inhibition	-	0.8748	87.48%
CYP2D6 inhibition	-	0.9283	92.83%
CYP1A2 inhibition	-	0.8355	83.55%
CYP2C8 inhibition	-	0.7492	74.92%
CYP inhibitory promiscuity	-	0.7558	75.58%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6558	65.58%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.9308	93.08%
Skin irritation	-	0.6358	63.58%
Skin corrosion	-	0.9740	97.40%
Ames mutagenesis	-	0.6828	68.28%
Human Ether-a-go-go-Related Gene inhibition	+	0.7375	73.75%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.6571	65.71%
skin sensitisation	-	0.6990	69.90%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5555	55.55%
Acute Oral Toxicity (c)	III	0.7214	72.14%
Estrogen receptor binding	+	0.6523	65.23%
Androgen receptor binding	-	0.5224	52.24%
Thyroid receptor binding	+	0.6088	60.88%
Glucocorticoid receptor binding	+	0.7861	78.61%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.5434	54.34%
Honey bee toxicity	-	0.8627	86.27%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9831	98.31%

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	94.92%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.43%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.20%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	89.88%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.32%	97.25%
CHEMBL1937	Q92769	Histone deacetylase 2	86.83%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.20%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.16%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.85%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.55%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.27%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.23%	89.00%

Plants that contains it

• Baccharis boliviensis

Cross-Links

• PubChem: 14262584
• LOTUS: LTS0157506
• wikiData: Q105240747