2-[(2R,4aR,5R,8aS)-5-hydroxy-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: e0d8dbae-bcb6-4f24-b902-6ba1eb4a3645
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aR,5R,8aS)-5-hydroxy-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC1=CCC(C2(C1CC(CC2)C(=C)C(=O)O)C)O
• SMILES (Isomeric): CC1=CC[C@H]([C@]2([C@H]1C[C@@H](CC2)C(=C)C(=O)O)C)O
• InChI: InChI=1S/C15H22O3/c1-9-4-5-13(16)15(3)7-6-11(8-12(9)15)10(2)14(17)18/h4,11-13,16H,2,5-8H2,1,3H3,(H,17,18)/t11-,12+,13-,15-/m1/s1
• InChI Key: CUDLWLJJPCDTLE-QVHKTLOISA-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: 2.60
• Atomic LogP (AlogP): 2.76
• 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	+	0.6378	63.78%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8131	81.31%
OATP2B1 inhibitior	-	0.8528	85.28%
OATP1B1 inhibitior	+	0.9170	91.70%
OATP1B3 inhibitior	+	0.9006	90.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5331	53.31%
BSEP inhibitior	-	0.8194	81.94%
P-glycoprotein inhibitior	-	0.9494	94.94%
P-glycoprotein substrate	-	0.8611	86.11%
CYP3A4 substrate	+	0.6214	62.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8817	88.17%
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	-	0.7911	79.11%
CYP inhibitory promiscuity	-	0.9359	93.59%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5465	54.65%
Eye corrosion	-	0.9939	99.39%
Eye irritation	-	0.6362	63.62%
Skin irritation	+	0.5902	59.02%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.6637	66.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5853	58.53%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	+	0.5333	53.33%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7896	78.96%
Acute Oral Toxicity (c)	III	0.7119	71.19%
Estrogen receptor binding	-	0.4813	48.13%
Androgen receptor binding	-	0.5274	52.74%
Thyroid receptor binding	-	0.5337	53.37%
Glucocorticoid receptor binding	+	0.5569	55.69%
Aromatase binding	-	0.6296	62.96%
PPAR gamma	+	0.6635	66.35%
Honey bee toxicity	-	0.9096	90.96%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.20%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.44%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	87.81%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.77%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.72%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.42%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.66%	93.04%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.00%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.83%	91.11%
CHEMBL2581	P07339	Cathepsin D	81.66%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	80.03%	91.19%

Plants that contains it

• Xanthium strumarium

Cross-Links

• PubChem: 14633048
• LOTUS: LTS0020654
• wikiData: Q104970190