2-[(2S,4S,4aS,8aS)-4-acetyloxy-4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: f195ff96-164e-4d5d-8b90-728f386e2fcd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2S,4S,4aS,8aS)-4-acetyloxy-4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC(=O)OC1CC(CC2C1(CCCC2=C)C)C(=C)C(=O)O
• SMILES (Isomeric): CC(=O)O[C@H]1C[C@H](C[C@@H]2[C@@]1(CCCC2=C)C)C(=C)C(=O)O
• InChI: InChI=1S/C17H24O4/c1-10-6-5-7-17(4)14(10)8-13(11(2)16(19)20)9-15(17)21-12(3)18/h13-15H,1-2,5-9H2,3-4H3,(H,19,20)/t13-,14-,15-,17-/m0/s1
• InChI Key: XWMQVMSNUBGDNJ-JKQORVJESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₄
• Molecular Weight: 292.40 g/mol
• Exact Mass: 292.16745924 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.33
• H-Bond Acceptor: 3
• 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	+	0.9844	98.44%
Caco-2	+	0.6688	66.88%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.8455	84.55%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.8451	84.51%
OATP1B3 inhibitior	+	0.8587	85.87%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.7771	77.71%
BSEP inhibitior	-	0.9301	93.01%
P-glycoprotein inhibitior	-	0.8096	80.96%
P-glycoprotein substrate	-	0.8847	88.47%
CYP3A4 substrate	+	0.6033	60.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9014	90.14%
CYP3A4 inhibition	-	0.6397	63.97%
CYP2C9 inhibition	-	0.9412	94.12%
CYP2C19 inhibition	-	0.9375	93.75%
CYP2D6 inhibition	-	0.9333	93.33%
CYP1A2 inhibition	-	0.6098	60.98%
CYP2C8 inhibition	-	0.7342	73.42%
CYP inhibitory promiscuity	-	0.9334	93.34%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.6272	62.72%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.7241	72.41%
Skin irritation	+	0.6198	61.98%
Skin corrosion	-	0.9586	95.86%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3896	38.96%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.6245	62.45%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.4767	47.67%
Acute Oral Toxicity (c)	III	0.8120	81.20%
Estrogen receptor binding	+	0.7856	78.56%
Androgen receptor binding	+	0.5413	54.13%
Thyroid receptor binding	-	0.5698	56.98%
Glucocorticoid receptor binding	+	0.6853	68.53%
Aromatase binding	-	0.5546	55.46%
PPAR gamma	+	0.6044	60.44%
Honey bee toxicity	-	0.8068	80.68%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6155	61.55%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.82%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.68%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.29%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	91.04%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.82%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.58%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.26%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.81%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.99%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	80.78%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.05%	97.09%

Plants that contains it

• Artemisia biennis

Cross-Links

• PubChem: 162909456
• LOTUS: LTS0197065
• wikiData: Q105343613