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

Details

• Internal ID: ef61a292-95ff-4f0f-b198-f5632fc54f6c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aR,8S,8aR)-8a-hydroxy-4a,8-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC1CCCC2(C1(CC(CC2)C(=C)C(=O)O)O)C
• SMILES (Isomeric): C[C@H]1CCC[C@]2([C@]1(C[C@@H](CC2)C(=C)C(=O)O)O)C
• InChI: InChI=1S/C15H24O3/c1-10-5-4-7-14(3)8-6-12(9-15(10,14)18)11(2)13(16)17/h10,12,18H,2,4-9H2,1,3H3,(H,16,17)/t10-,12+,14+,15+/m0/s1
• InChI Key: ITEOVFZKXCDRFX-QMGNLALYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.35 g/mol
• Exact Mass: 252.17254462 g/mol
• Topological Polar Surface Area (TPSA): 57.50 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.98
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9956	99.56%
Caco-2	+	0.7609	76.09%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8131	81.31%
OATP2B1 inhibitior	-	0.8501	85.01%
OATP1B1 inhibitior	+	0.9340	93.40%
OATP1B3 inhibitior	+	0.9006	90.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5331	53.31%
BSEP inhibitior	-	0.8986	89.86%
P-glycoprotein inhibitior	-	0.9398	93.98%
P-glycoprotein substrate	-	0.8515	85.15%
CYP3A4 substrate	+	0.5427	54.27%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9029	90.29%
CYP3A4 inhibition	-	0.7164	71.64%
CYP2C9 inhibition	-	0.9340	93.40%
CYP2C19 inhibition	-	0.9066	90.66%
CYP2D6 inhibition	-	0.9421	94.21%
CYP1A2 inhibition	-	0.8956	89.56%
CYP2C8 inhibition	-	0.8582	85.82%
CYP inhibitory promiscuity	-	0.9359	93.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5465	54.65%
Eye corrosion	-	0.9939	99.39%
Eye irritation	-	0.6005	60.05%
Skin irritation	+	0.5902	59.02%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.7237	72.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.7291	72.91%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5085	50.85%
skin sensitisation	+	0.5333	53.33%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.4559	45.59%
Acute Oral Toxicity (c)	III	0.7119	71.19%
Estrogen receptor binding	+	0.7566	75.66%
Androgen receptor binding	-	0.5849	58.49%
Thyroid receptor binding	-	0.6039	60.39%
Glucocorticoid receptor binding	+	0.6985	69.85%
Aromatase binding	+	0.6980	69.80%
PPAR gamma	+	0.5706	57.06%
Honey bee toxicity	-	0.9334	93.34%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9968	99.68%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.61%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.87%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	89.64%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.34%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.34%	96.61%
CHEMBL340	P08684	Cytochrome P450 3A4	87.21%	91.19%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.97%	96.38%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.16%	95.50%
CHEMBL206	P03372	Estrogen receptor alpha	83.74%	97.64%
CHEMBL221	P23219	Cyclooxygenase-1	82.96%	90.17%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.58%	82.69%

Plants that contains it

• Apalochlamys spectabilis
• Aster himalaicus
• Chiliadenus montanus

Cross-Links

• PubChem: 101589316
• LOTUS: LTS0069757
• wikiData: Q105119995