2-(4-acetyloxy-8a-hydroxy-4a-methyl-8-methylidene-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl)prop-2-enoic acid

Details

• Internal ID: 551cf712-2db8-43ef-adf1-256b6d05b0de
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-(4-acetyloxy-8a-hydroxy-4a-methyl-8-methylidene-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl)prop-2-enoic acid
• SMILES (Canonical): CC(=O)OC1CC(CC2(C1(CCCC2=C)C)O)C(=C)C(=O)O
• SMILES (Isomeric): CC(=O)OC1CC(CC2(C1(CCCC2=C)C)O)C(=C)C(=O)O
• InChI: InChI=1S/C17H24O5/c1-10-6-5-7-16(4)14(22-12(3)18)8-13(9-17(10,16)21)11(2)15(19)20/h13-14,21H,1-2,5-9H2,3-4H3,(H,19,20)
• InChI Key: GRAPHCHSEGTYRN-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₅
• Molecular Weight: 308.40 g/mol
• Exact Mass: 308.16237386 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.45
• 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	+	0.9871	98.71%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8425	84.25%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.8851	88.51%
OATP1B3 inhibitior	-	0.2316	23.16%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7137	71.37%
BSEP inhibitior	-	0.9228	92.28%
P-glycoprotein inhibitior	-	0.8641	86.41%
P-glycoprotein substrate	-	0.8645	86.45%
CYP3A4 substrate	+	0.6142	61.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9071	90.71%
CYP3A4 inhibition	-	0.6740	67.40%
CYP2C9 inhibition	-	0.9029	90.29%
CYP2C19 inhibition	-	0.9106	91.06%
CYP2D6 inhibition	-	0.9482	94.82%
CYP1A2 inhibition	-	0.7906	79.06%
CYP2C8 inhibition	-	0.6345	63.45%
CYP inhibitory promiscuity	-	0.9587	95.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9543	95.43%
Carcinogenicity (trinary)	Non-required	0.5998	59.98%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.7720	77.20%
Skin irritation	+	0.5823	58.23%
Skin corrosion	-	0.9381	93.81%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5120	51.20%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.7020	70.20%
Respiratory toxicity	-	0.7222	72.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.5947	59.47%
Acute Oral Toxicity (c)	I	0.4889	48.89%
Estrogen receptor binding	+	0.7509	75.09%
Androgen receptor binding	+	0.5577	55.77%
Thyroid receptor binding	-	0.5591	55.91%
Glucocorticoid receptor binding	+	0.7347	73.47%
Aromatase binding	+	0.5500	55.00%
PPAR gamma	+	0.5615	56.15%
Honey bee toxicity	-	0.8255	82.55%
Biodegradation	-	0.6250	62.50%
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	95.62%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.17%	91.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.13%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	89.83%	91.19%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.21%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.68%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.64%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.09%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.31%	94.45%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.61%	82.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.38%	100.00%

Plants that contains it

• Artemisia biennis

Cross-Links

• PubChem: 162854247
• LOTUS: LTS0017642
• wikiData: Q105015664