[(4aS,5R,8S,8aR)-8-hydroxy-5-methyl-8-propan-2-yl-4,4a,5,6,7,8a-hexahydro-3H-naphthalen-2-yl]methyl 2-phenylacetate

Details

• Internal ID: b5353d0e-d3c8-4b97-b079-bff26348f65e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(4aS,5R,8S,8aR)-8-hydroxy-5-methyl-8-propan-2-yl-4,4a,5,6,7,8a-hexahydro-3H-naphthalen-2-yl]methyl 2-phenylacetate
• SMILES (Canonical): CC1CCC(C2C1CCC(=C2)COC(=O)CC3=CC=CC=C3)(C(C)C)O
• SMILES (Isomeric): C[C@@H]1CC[C@@]([C@@H]2[C@H]1CCC(=C2)COC(=O)CC3=CC=CC=C3)(C(C)C)O
• InChI: InChI=1S/C23H32O3/c1-16(2)23(25)12-11-17(3)20-10-9-19(13-21(20)23)15-26-22(24)14-18-7-5-4-6-8-18/h4-8,13,16-17,20-21,25H,9-12,14-15H2,1-3H3/t17-,20+,21+,23+/m1/s1
• InChI Key: AXHPCMJFAOEIJI-NPWUYRIISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₂O₃
• Molecular Weight: 356.50 g/mol
• Exact Mass: 356.23514488 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 4.60
• Atomic LogP (AlogP): 4.54
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	1.0000	100.00%
Caco-2	+	0.5408	54.08%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8811	88.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9005	90.05%
OATP1B3 inhibitior	+	0.9384	93.84%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.9682	96.82%
P-glycoprotein inhibitior	-	0.4506	45.06%
P-glycoprotein substrate	-	0.6575	65.75%
CYP3A4 substrate	+	0.6318	63.18%
CYP2C9 substrate	-	0.6124	61.24%
CYP2D6 substrate	-	0.8370	83.70%
CYP3A4 inhibition	-	0.7391	73.91%
CYP2C9 inhibition	+	0.5863	58.63%
CYP2C19 inhibition	+	0.5887	58.87%
CYP2D6 inhibition	-	0.8844	88.44%
CYP1A2 inhibition	-	0.7112	71.12%
CYP2C8 inhibition	-	0.5572	55.72%
CYP inhibitory promiscuity	-	0.7375	73.75%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5983	59.83%
Eye corrosion	-	0.9945	99.45%
Eye irritation	-	0.9323	93.23%
Skin irritation	-	0.7061	70.61%
Skin corrosion	-	0.9800	98.00%
Ames mutagenesis	-	0.8270	82.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7946	79.46%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5209	52.09%
skin sensitisation	-	0.6325	63.25%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.9255	92.55%
Acute Oral Toxicity (c)	III	0.7399	73.99%
Estrogen receptor binding	+	0.8947	89.47%
Androgen receptor binding	+	0.5652	56.52%
Thyroid receptor binding	+	0.6667	66.67%
Glucocorticoid receptor binding	+	0.6683	66.83%
Aromatase binding	+	0.6036	60.36%
PPAR gamma	+	0.6898	68.98%
Honey bee toxicity	-	0.8871	88.71%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5545	55.45%
Fish aquatic toxicity	+	0.9968	99.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.88%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	97.78%	90.17%
CHEMBL2581	P07339	Cathepsin D	96.90%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.21%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.94%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.22%	97.25%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.59%	100.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.33%	94.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.61%	95.89%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.64%	97.09%
CHEMBL5028	O14672	ADAM10	80.42%	97.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.01%	94.08%

Plants that contains it

• Fabiana imbricata

Cross-Links

• PubChem: 162951566
• LOTUS: LTS0212458
• wikiData: Q104920547