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

Details

• Internal ID: ca0ce141-1f4f-472e-b9ff-e655d8e3089c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aS,7R,8aR)-7-hydroxy-4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC12CCC(CC1C(=C)C(CC2)O)C(=C)C(=O)O
• SMILES (Isomeric): C[C@@]12CC[C@H](C[C@H]1C(=C)[C@@H](CC2)O)C(=C)C(=O)O
• InChI: InChI=1S/C15H22O3/c1-9(14(17)18)11-4-6-15(3)7-5-13(16)10(2)12(15)8-11/h11-13,16H,1-2,4-8H2,3H3,(H,17,18)/t11-,12+,13-,15+/m1/s1
• InChI Key: GQDFYCPPHMEHJL-COMQUAJESA-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: 2.70
• 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	+	0.9964	99.64%
Caco-2	+	0.5557	55.57%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8072	80.72%
OATP2B1 inhibitior	-	0.8511	85.11%
OATP1B1 inhibitior	+	0.9288	92.88%
OATP1B3 inhibitior	+	0.9181	91.81%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5181	51.81%
BSEP inhibitior	-	0.9023	90.23%
P-glycoprotein inhibitior	-	0.9235	92.35%
P-glycoprotein substrate	-	0.8605	86.05%
CYP3A4 substrate	+	0.5569	55.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8817	88.17%
CYP3A4 inhibition	-	0.8014	80.14%
CYP2C9 inhibition	-	0.9210	92.10%
CYP2C19 inhibition	-	0.8161	81.61%
CYP2D6 inhibition	-	0.9294	92.94%
CYP1A2 inhibition	-	0.8678	86.78%
CYP2C8 inhibition	-	0.8586	85.86%
CYP inhibitory promiscuity	-	0.9327	93.27%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5391	53.91%
Eye corrosion	-	0.9902	99.02%
Eye irritation	+	0.6834	68.34%
Skin irritation	+	0.5285	52.85%
Skin corrosion	-	0.9321	93.21%
Ames mutagenesis	-	0.6537	65.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5513	55.13%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.4786	47.86%
Acute Oral Toxicity (c)	III	0.6963	69.63%
Estrogen receptor binding	+	0.5880	58.80%
Androgen receptor binding	-	0.5065	50.65%
Thyroid receptor binding	-	0.5756	57.56%
Glucocorticoid receptor binding	+	0.7167	71.67%
Aromatase binding	-	0.5811	58.11%
PPAR gamma	-	0.5394	53.94%
Honey bee toxicity	-	0.9037	90.37%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9956	99.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	94.95%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.37%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.26%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.40%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	81.89%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.36%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	81.15%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.99%	100.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.28%	93.03%

Plants that contains it

• Aster himalaicus
• Dittrichia graveolens
• Dittrichia viscosa subsp. viscosa

Cross-Links

• PubChem: 38348725
• LOTUS: LTS0159641
• wikiData: Q104398831