2-[(2R,4aS,7S,8R)-7-hydroxy-4a,8-dimethyl-3,4,5,6,7,8-hexahydro-2H-naphthalen-2-yl]prop-2-enoic acid

Details

• Internal ID: ec4039f5-ca7c-4747-a234-c920b64605fc
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4aS,7S,8R)-7-hydroxy-4a,8-dimethyl-3,4,5,6,7,8-hexahydro-2H-naphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC1C(CCC2(C1=CC(CC2)C(=C)C(=O)O)C)O
• SMILES (Isomeric): C[C@H]1[C@H](CC[C@]2(C1=C[C@@H](CC2)C(=C)C(=O)O)C)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/h8,10-11,13,16H,1,4-7H2,2-3H3,(H,17,18)/t10-,11-,13+,15+/m1/s1
• InChI Key: BPFONPLOHQYTOT-ZSEWYUTFSA-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	+	0.9961	99.61%
Caco-2	+	0.7870	78.70%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8327	83.27%
OATP2B1 inhibitior	-	0.8528	85.28%
OATP1B1 inhibitior	+	0.8782	87.82%
OATP1B3 inhibitior	+	0.9306	93.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5581	55.81%
BSEP inhibitior	-	0.9478	94.78%
P-glycoprotein inhibitior	-	0.9059	90.59%
P-glycoprotein substrate	-	0.8423	84.23%
CYP3A4 substrate	+	0.5724	57.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8817	88.17%
CYP3A4 inhibition	-	0.7949	79.49%
CYP2C9 inhibition	-	0.9223	92.23%
CYP2C19 inhibition	-	0.8967	89.67%
CYP2D6 inhibition	-	0.9354	93.54%
CYP1A2 inhibition	-	0.8896	88.96%
CYP2C8 inhibition	-	0.8731	87.31%
CYP inhibitory promiscuity	-	0.9348	93.48%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5394	53.94%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.7680	76.80%
Skin irritation	+	0.5831	58.31%
Skin corrosion	-	0.9459	94.59%
Ames mutagenesis	-	0.7582	75.82%
Human Ether-a-go-go-Related Gene inhibition	-	0.6422	64.22%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.6125	61.25%
skin sensitisation	-	0.5368	53.68%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6289	62.89%
Acute Oral Toxicity (c)	III	0.7004	70.04%
Estrogen receptor binding	-	0.6989	69.89%
Androgen receptor binding	-	0.6722	67.22%
Thyroid receptor binding	-	0.5600	56.00%
Glucocorticoid receptor binding	-	0.5116	51.16%
Aromatase binding	+	0.6065	60.65%
PPAR gamma	-	0.5803	58.03%
Honey bee toxicity	-	0.9447	94.47%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7200	72.00%
Fish aquatic toxicity	+	0.9971	99.71%

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	95.21%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.44%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.92%	95.56%
CHEMBL2581	P07339	Cathepsin D	83.09%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	82.92%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.69%	97.25%

Plants that contains it

• Laggera crispata

Cross-Links

• PubChem: 162923341
• LOTUS: LTS0204834
• wikiData: Q104942121