2-[(2R,4aS,7R,8S,8aR)-7-acetyloxy-8-hydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: 88ee6070-e7b7-43be-8649-6e8ae3aa03a6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aS,7R,8S,8aR)-7-acetyloxy-8-hydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC(=O)OC1CCC2(CCC(CC2C1(C)O)C(=C)C(=O)O)C
• SMILES (Isomeric): CC(=O)O[C@@H]1CC[C@@]2(CC[C@H](C[C@H]2[C@]1(C)O)C(=C)C(=O)O)C
• InChI: InChI=1S/C17H26O5/c1-10(15(19)20)12-5-7-16(3)8-6-14(22-11(2)18)17(4,21)13(16)9-12/h12-14,21H,1,5-9H2,2-4H3,(H,19,20)/t12-,13-,14-,16+,17+/m1/s1
• InChI Key: POZYOVPQCDLBIQ-VJDWVQAOSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₆O₅
• Molecular Weight: 310.40 g/mol
• Exact Mass: 310.17802393 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 2.53
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9798	97.98%
Caco-2	+	0.6130	61.30%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8526	85.26%
OATP2B1 inhibitior	-	0.8580	85.80%
OATP1B1 inhibitior	+	0.9271	92.71%
OATP1B3 inhibitior	-	0.3386	33.86%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.6842	68.42%
BSEP inhibitior	-	0.9308	93.08%
P-glycoprotein inhibitior	-	0.8414	84.14%
P-glycoprotein substrate	-	0.8790	87.90%
CYP3A4 substrate	+	0.6239	62.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	-	0.6920	69.20%
CYP2C9 inhibition	-	0.9167	91.67%
CYP2C19 inhibition	-	0.9017	90.17%
CYP2D6 inhibition	-	0.9393	93.93%
CYP1A2 inhibition	-	0.7396	73.96%
CYP2C8 inhibition	-	0.7113	71.13%
CYP inhibitory promiscuity	-	0.9455	94.55%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9743	97.43%
Carcinogenicity (trinary)	Non-required	0.6580	65.80%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.8508	85.08%
Skin irritation	+	0.5996	59.96%
Skin corrosion	-	0.9575	95.75%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5228	52.28%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.5342	53.42%
skin sensitisation	-	0.6662	66.62%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.5832	58.32%
Acute Oral Toxicity (c)	III	0.5899	58.99%
Estrogen receptor binding	+	0.8069	80.69%
Androgen receptor binding	-	0.5074	50.74%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7616	76.16%
Aromatase binding	+	0.6411	64.11%
PPAR gamma	+	0.7023	70.23%
Honey bee toxicity	-	0.7314	73.14%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5755	57.55%
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	94.51%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.92%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	90.36%	91.19%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.11%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.38%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.10%	97.09%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.20%	82.69%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.37%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.18%	92.94%

Plants that contains it

• Haeckeria punctulata
• Ozothamnus pholidotus

Cross-Links

• PubChem: 15699303
• LOTUS: LTS0020670
• wikiData: Q105212776