[2,3-Dihydroxy-3,4a,8,8-tetramethyl-4-(3-oxobut-1-enyl)-2,4,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate

Details

• Internal ID: d6ea02c0-5ed1-4611-8a28-90b0647dd337
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [2,3-dihydroxy-3,4a,8,8-tetramethyl-4-(3-oxobut-1-enyl)-2,4,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate
• SMILES (Canonical): CC(=O)C=CC1C2(CCCC(C2C(C(C1(C)O)O)OC(=O)C)(C)C)C
• SMILES (Isomeric): CC(=O)C=CC1C2(CCCC(C2C(C(C1(C)O)O)OC(=O)C)(C)C)C
• InChI: InChI=1S/C20H32O5/c1-12(21)8-9-14-19(5)11-7-10-18(3,4)16(19)15(25-13(2)22)17(23)20(14,6)24/h8-9,14-17,23-24H,7,10-11H2,1-6H3
• InChI Key: BNOWPELKBYSHKU-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.50 g/mol
• Exact Mass: 352.22497412 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.64
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• [2,3-Dihydroxy-3,4a,8,8-tetramethyl-4-(3-oxobut-1-enyl)-2,4,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9528	95.28%
Caco-2	-	0.5283	52.83%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7972	79.72%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8666	86.66%
OATP1B3 inhibitior	+	0.8839	88.39%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.7629	76.29%
P-glycoprotein inhibitior	-	0.7313	73.13%
P-glycoprotein substrate	-	0.8459	84.59%
CYP3A4 substrate	+	0.6257	62.57%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9120	91.20%
CYP3A4 inhibition	-	0.8592	85.92%
CYP2C9 inhibition	-	0.8467	84.67%
CYP2C19 inhibition	-	0.8672	86.72%
CYP2D6 inhibition	-	0.9519	95.19%
CYP1A2 inhibition	-	0.6412	64.12%
CYP2C8 inhibition	-	0.7932	79.32%
CYP inhibitory promiscuity	-	0.9589	95.89%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.6159	61.59%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9695	96.95%
Skin irritation	-	0.5218	52.18%
Skin corrosion	-	0.9227	92.27%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6066	60.66%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5635	56.35%
skin sensitisation	-	0.6653	66.53%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5216	52.16%
Acute Oral Toxicity (c)	III	0.6157	61.57%
Estrogen receptor binding	+	0.6546	65.46%
Androgen receptor binding	-	0.6014	60.14%
Thyroid receptor binding	+	0.6088	60.88%
Glucocorticoid receptor binding	+	0.7297	72.97%
Aromatase binding	-	0.5273	52.73%
PPAR gamma	-	0.4900	49.00%
Honey bee toxicity	-	0.7897	78.97%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7055	70.55%
Fish aquatic toxicity	+	0.9960	99.60%

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	94.64%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.34%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.87%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	87.67%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.99%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.64%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	83.27%	94.75%
CHEMBL2581	P07339	Cathepsin D	83.12%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.52%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.89%	86.33%

Plants that contains it

• Stevia rebaudiana

Cross-Links

• PubChem: 73823951
• LOTUS: LTS0193982
• wikiData: Q104938953