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

Details

• Internal ID: 65947cda-5a08-4513-b6e2-b95486f4f657
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: 2-[(2R,4aS,8R,8aR)-8-hydroxy-4a,8-dimethyl-1,2,3,4,5,8a-hexahydronaphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC12CCC(CC1C(C=CC2)(C)O)C(=C)C(=O)O
• SMILES (Isomeric): C[C@@]12CC[C@H](C[C@H]1[C@](C=CC2)(C)O)C(=C)C(=O)O
• InChI: InChI=1S/C15H22O3/c1-10(13(16)17)11-5-8-14(2)6-4-7-15(3,18)12(14)9-11/h4,7,11-12,18H,1,5-6,8-9H2,2-3H3,(H,16,17)/t11-,12-,14-,15-/m1/s1
• InChI Key: PMMASMOTSKQUBU-QHSBEEBCSA-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: 2.80
• 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	+	0.9951	99.51%
Caco-2	+	0.7242	72.42%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7753	77.53%
OATP2B1 inhibitior	-	0.8520	85.20%
OATP1B1 inhibitior	+	0.9335	93.35%
OATP1B3 inhibitior	+	0.8470	84.70%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5069	50.69%
BSEP inhibitior	-	0.8515	85.15%
P-glycoprotein inhibitior	-	0.9399	93.99%
P-glycoprotein substrate	-	0.8503	85.03%
CYP3A4 substrate	+	0.5631	56.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9003	90.03%
CYP3A4 inhibition	-	0.7538	75.38%
CYP2C9 inhibition	-	0.7909	79.09%
CYP2C19 inhibition	-	0.8319	83.19%
CYP2D6 inhibition	-	0.9062	90.62%
CYP1A2 inhibition	-	0.7871	78.71%
CYP2C8 inhibition	-	0.7517	75.17%
CYP inhibitory promiscuity	-	0.8834	88.34%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5394	53.94%
Eye corrosion	-	0.9860	98.60%
Eye irritation	-	0.7165	71.65%
Skin irritation	-	0.5600	56.00%
Skin corrosion	-	0.9634	96.34%
Ames mutagenesis	-	0.6137	61.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6494	64.94%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.5014	50.14%
skin sensitisation	+	0.6449	64.49%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.7632	76.32%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.4672	46.72%
Acute Oral Toxicity (c)	III	0.7353	73.53%
Estrogen receptor binding	+	0.6015	60.15%
Androgen receptor binding	-	0.6445	64.45%
Thyroid receptor binding	+	0.5496	54.96%
Glucocorticoid receptor binding	+	0.7079	70.79%
Aromatase binding	+	0.5201	52.01%
PPAR gamma	+	0.5824	58.24%
Honey bee toxicity	-	0.8803	88.03%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.47%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.10%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	90.81%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.28%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	88.06%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.44%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	82.09%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.32%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.50%	100.00%

Plants that contains it

• Dittrichia graveolens

Cross-Links

• PubChem: 162842573
• LOTUS: LTS0173460
• wikiData: Q105211584