[(1R,3S,4R,4aR,8aR)-3-acetyloxy-4-hydroxy-4,8a-dimethyl-6-propan-2-yl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl] acetate

Details

• Internal ID: b1ef7337-171f-48a7-8a4a-9c10f6318617
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1R,3S,4R,4aR,8aR)-3-acetyloxy-4-hydroxy-4,8a-dimethyl-6-propan-2-yl-1,2,3,4a,5,8-hexahydronaphthalen-1-yl] acetate
• SMILES (Canonical): CC(C)C1=CCC2(C(CC(C(C2C1)(C)O)OC(=O)C)OC(=O)C)C
• SMILES (Isomeric): CC(C)C1=CC[C@]2([C@@H](C[C@@H]([C@]([C@@H]2C1)(C)O)OC(=O)C)OC(=O)C)C
• InChI: InChI=1S/C19H30O5/c1-11(2)14-7-8-18(5)15(9-14)19(6,22)17(24-13(4)21)10-16(18)23-12(3)20/h7,11,15-17,22H,8-10H2,1-6H3/t15-,16-,17+,18-,19-/m1/s1
• InChI Key: CTASSTCAVUQMJI-UJWQCDCRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₃₀O₅
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.20932405 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.00
• H-Bond Acceptor: 5
• 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	+	0.9920	99.20%
Caco-2	-	0.5262	52.62%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8496	84.96%
OATP2B1 inhibitior	-	0.8576	85.76%
OATP1B1 inhibitior	+	0.9155	91.55%
OATP1B3 inhibitior	-	0.2610	26.10%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8393	83.93%
P-glycoprotein inhibitior	-	0.6277	62.77%
P-glycoprotein substrate	-	0.8363	83.63%
CYP3A4 substrate	+	0.6012	60.12%
CYP2C9 substrate	-	0.7912	79.12%
CYP2D6 substrate	-	0.8744	87.44%
CYP3A4 inhibition	-	0.6960	69.60%
CYP2C9 inhibition	-	0.8576	85.76%
CYP2C19 inhibition	-	0.7907	79.07%
CYP2D6 inhibition	-	0.9573	95.73%
CYP1A2 inhibition	-	0.7585	75.85%
CYP2C8 inhibition	-	0.8759	87.59%
CYP inhibitory promiscuity	-	0.9342	93.42%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9843	98.43%
Carcinogenicity (trinary)	Non-required	0.5858	58.58%
Eye corrosion	-	0.9922	99.22%
Eye irritation	-	0.8451	84.51%
Skin irritation	-	0.5262	52.62%
Skin corrosion	-	0.9655	96.55%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5257	52.57%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.5176	51.76%
skin sensitisation	-	0.6101	61.01%
Respiratory toxicity	-	0.6333	63.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4558	45.58%
Estrogen receptor binding	+	0.7831	78.31%
Androgen receptor binding	-	0.5746	57.46%
Thyroid receptor binding	+	0.5725	57.25%
Glucocorticoid receptor binding	-	0.5426	54.26%
Aromatase binding	-	0.6314	63.14%
PPAR gamma	+	0.7304	73.04%
Honey bee toxicity	-	0.8219	82.19%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	1.0000	100.00%

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	97.26%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.06%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.65%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	90.64%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.60%	97.25%
CHEMBL2581	P07339	Cathepsin D	86.67%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.53%	97.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.29%	93.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.82%	94.08%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.04%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.68%	100.00%

Plants that contains it

• Pallenis spinosa

Cross-Links

• PubChem: 14733709
• LOTUS: LTS0269529
• wikiData: Q104969676