2-[(2R,4aR)-8-(hydroxymethyl)-4a-methyl-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: a5eec109-adc2-42f9-8556-ee43b5c14844
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aR)-8-(hydroxymethyl)-4a-methyl-2,3,4,5,6,7-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC12CCCC(=C1CC(CC2)C(=C)C(=O)O)CO
• SMILES (Isomeric): C[C@]12CCCC(=C1C[C@@H](CC2)C(=C)C(=O)O)CO
• InChI: InChI=1S/C15H22O3/c1-10(14(17)18)11-5-7-15(2)6-3-4-12(9-16)13(15)8-11/h11,16H,1,3-9H2,2H3,(H,17,18)/t11-,15-/m1/s1
• InChI Key: AZBXHHKPJVBKTN-IAQYHMDHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.33 g/mol
• Exact Mass: 250.15689456 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.91
• H-Bond Acceptor: 2
• 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	+	0.9909	99.09%
Caco-2	+	0.6854	68.54%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6244	62.44%
OATP2B1 inhibitior	-	0.8496	84.96%
OATP1B1 inhibitior	+	0.8859	88.59%
OATP1B3 inhibitior	+	0.8376	83.76%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5422	54.22%
BSEP inhibitior	-	0.7771	77.71%
P-glycoprotein inhibitior	-	0.9391	93.91%
P-glycoprotein substrate	-	0.8448	84.48%
CYP3A4 substrate	+	0.5391	53.91%
CYP2C9 substrate	-	0.8129	81.29%
CYP2D6 substrate	-	0.8957	89.57%
CYP3A4 inhibition	-	0.7546	75.46%
CYP2C9 inhibition	-	0.5610	56.10%
CYP2C19 inhibition	-	0.7057	70.57%
CYP2D6 inhibition	-	0.8934	89.34%
CYP1A2 inhibition	-	0.7274	72.74%
CYP2C8 inhibition	-	0.8019	80.19%
CYP inhibitory promiscuity	-	0.7730	77.30%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6205	62.05%
Eye corrosion	-	0.9651	96.51%
Eye irritation	+	0.8072	80.72%
Skin irritation	-	0.7924	79.24%
Skin corrosion	-	0.9718	97.18%
Ames mutagenesis	-	0.5137	51.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5476	54.76%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.5993	59.93%
skin sensitisation	-	0.5744	57.44%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.5672	56.72%
Acute Oral Toxicity (c)	III	0.5891	58.91%
Estrogen receptor binding	-	0.6626	66.26%
Androgen receptor binding	-	0.5583	55.83%
Thyroid receptor binding	-	0.5834	58.34%
Glucocorticoid receptor binding	+	0.5641	56.41%
Aromatase binding	+	0.5458	54.58%
PPAR gamma	-	0.5159	51.59%
Honey bee toxicity	-	0.9394	93.94%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.6300	63.00%
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	95.52%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.69%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.98%	97.25%
CHEMBL233	P35372	Mu opioid receptor	91.30%	97.93%
CHEMBL2581	P07339	Cathepsin D	90.66%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.30%	97.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.45%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.41%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.64%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	80.88%	91.19%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.07%	100.00%

Plants that contains it

• Pluchea dioscoridis

Cross-Links

• PubChem: 163059403
• LOTUS: LTS0116667
• wikiData: Q104921596