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

Details

• Internal ID: 6f0e7503-145a-4b97-a6b7-89e6ed48f495
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aR,5R,8aS)-5-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)CCC2O)C(=C)C(=O)O
• SMILES (Isomeric): C[C@@]12CC[C@H](C[C@H]1C(=C)CC[C@H]2O)C(=C)C(=O)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/h11-13,16H,1-2,4-8H2,3H3,(H,17,18)/t11-,12+,13-,15-/m1/s1
• InChI Key: GQPJZGWMHPSVIQ-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	+	0.9959	99.59%
Caco-2	+	0.5662	56.62%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7986	79.86%
OATP2B1 inhibitior	-	0.8539	85.39%
OATP1B1 inhibitior	+	0.9113	91.13%
OATP1B3 inhibitior	+	0.9046	90.46%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5931	59.31%
BSEP inhibitior	-	0.8672	86.72%
P-glycoprotein inhibitior	-	0.9404	94.04%
P-glycoprotein substrate	-	0.8633	86.33%
CYP3A4 substrate	+	0.6171	61.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8817	88.17%
CYP3A4 inhibition	-	0.7834	78.34%
CYP2C9 inhibition	-	0.9308	93.08%
CYP2C19 inhibition	-	0.8515	85.15%
CYP2D6 inhibition	-	0.9456	94.56%
CYP1A2 inhibition	-	0.8542	85.42%
CYP2C8 inhibition	-	0.8595	85.95%
CYP inhibitory promiscuity	-	0.9407	94.07%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5246	52.46%
Eye corrosion	-	0.9928	99.28%
Eye irritation	-	0.4777	47.77%
Skin irritation	+	0.5904	59.04%
Skin corrosion	-	0.9369	93.69%
Ames mutagenesis	-	0.6437	64.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.5779	57.79%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	+	0.4909	49.09%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7318	73.18%
Acute Oral Toxicity (c)	III	0.7160	71.60%
Estrogen receptor binding	+	0.7732	77.32%
Androgen receptor binding	+	0.5920	59.20%
Thyroid receptor binding	-	0.5586	55.86%
Glucocorticoid receptor binding	+	0.6997	69.97%
Aromatase binding	-	0.5592	55.92%
PPAR gamma	+	0.6002	60.02%
Honey bee toxicity	-	0.9200	92.00%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9960	99.60%

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	94.36%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	94.01%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.11%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.66%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	85.33%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.74%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.81%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.29%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.73%	96.38%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.47%	99.23%

Plants that contains it

• Dittrichia graveolens
• Laggera alata
• Xanthium strumarium

Cross-Links

• PubChem: 14633051
• LOTUS: LTS0051024
• wikiData: Q105015517