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

Details

• Internal ID: 7e02d03d-63fe-4eba-85da-85b4211aa35a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aS,6S,8aR)-6-hydroxy-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC1=CC(CC2(C1CC(CC2)C(=C)C(=O)O)C)O
• SMILES (Isomeric): CC1=C[C@H](C[C@]2([C@H]1C[C@@H](CC2)C(=C)C(=O)O)C)O
• InChI: InChI=1S/C15H22O3/c1-9-6-12(16)8-15(3)5-4-11(7-13(9)15)10(2)14(17)18/h6,11-13,16H,2,4-5,7-8H2,1,3H3,(H,17,18)/t11-,12-,13+,15+/m1/s1
• InChI Key: SKQMBUGVSOITND-CXTNEJHOSA-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	+	0.9944	99.44%
Caco-2	+	0.7291	72.91%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7037	70.37%
OATP2B1 inhibitior	-	0.8533	85.33%
OATP1B1 inhibitior	+	0.9102	91.02%
OATP1B3 inhibitior	+	0.9251	92.51%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5081	50.81%
BSEP inhibitior	-	0.9333	93.33%
P-glycoprotein inhibitior	-	0.9285	92.85%
P-glycoprotein substrate	-	0.8579	85.79%
CYP3A4 substrate	+	0.5694	56.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8817	88.17%
CYP3A4 inhibition	-	0.7192	71.92%
CYP2C9 inhibition	-	0.9031	90.31%
CYP2C19 inhibition	-	0.8916	89.16%
CYP2D6 inhibition	-	0.9300	93.00%
CYP1A2 inhibition	-	0.8235	82.35%
CYP2C8 inhibition	-	0.8381	83.81%
CYP inhibitory promiscuity	-	0.9309	93.09%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5559	55.59%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.8371	83.71%
Skin irritation	+	0.5377	53.77%
Skin corrosion	-	0.9536	95.36%
Ames mutagenesis	-	0.6137	61.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5279	52.79%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	+	0.5585	55.85%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.8299	82.99%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7555	75.55%
Acute Oral Toxicity (c)	III	0.8068	80.68%
Estrogen receptor binding	+	0.6395	63.95%
Androgen receptor binding	-	0.6326	63.26%
Thyroid receptor binding	-	0.5301	53.01%
Glucocorticoid receptor binding	+	0.5889	58.89%
Aromatase binding	-	0.5322	53.22%
PPAR gamma	+	0.6085	60.85%
Honey bee toxicity	-	0.9068	90.68%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9932	99.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.38%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.38%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.32%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.74%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.68%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.23%	97.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.02%	93.03%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.62%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.91%	100.00%
CHEMBL4208	P20618	Proteasome component C5	81.13%	90.00%

Plants that contains it

• Dittrichia graveolens

Cross-Links

• PubChem: 101607193
• LOTUS: LTS0222991
• wikiData: Q105254993