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

Details

• Internal ID: aa09550b-b9bf-4190-b920-92a1e1b44a93
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,3R,4aR,8aS)-3-acetyloxy-4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid
• InChI: InChI=1S/C17H24O4/c1-10-6-5-7-17(4)9-15(21-12(3)18)13(8-14(10)17)11(2)16(19)20/h13-15H,1-2,5-9H2,3-4H3,(H,19,20)/t13-,14+,15-,17-/m1/s1
• InChI Key: IXUSCHCZPPDBLM-JYYAWHABSA-N
• Popularity: 2 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	+	0.6022	60.22%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8455	84.55%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.8964	89.64%
OATP1B3 inhibitior	+	0.8587	85.87%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.7771	77.71%
BSEP inhibitior	-	0.9210	92.10%
P-glycoprotein inhibitior	-	0.8693	86.93%
P-glycoprotein substrate	-	0.8407	84.07%
CYP3A4 substrate	+	0.6241	62.41%
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	-	0.7878	78.78%
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	-	0.6828	68.28%
Skin irritation	+	0.6198	61.98%
Skin corrosion	-	0.9586	95.86%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5958	59.58%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.6245	62.45%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6198	61.98%
Acute Oral Toxicity (c)	III	0.8120	81.20%
Estrogen receptor binding	+	0.6696	66.96%
Androgen receptor binding	+	0.5559	55.59%
Thyroid receptor binding	+	0.5343	53.43%
Glucocorticoid receptor binding	+	0.6810	68.10%
Aromatase binding	-	0.5212	52.12%
PPAR gamma	-	0.5061	50.61%
Honey bee toxicity	-	0.7788	77.88%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6955	69.55%
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
CHEMBL221	P23219	Cyclooxygenase-1	95.51%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.03%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.48%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	91.36%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.63%	94.45%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	86.89%	95.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	86.15%	94.08%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.77%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.43%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.20%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.49%	86.33%

Plants that contains it

• Geigeria rigida

Cross-Links

• PubChem: 14414333
• LOTUS: LTS0181445
• wikiData: Q105122497