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

Details

• Internal ID: 8680eecd-6ba0-40c8-ac73-347216436e16
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids
• IUPAC Name: 2-[(2R,4S,4aR,5R,8S)-4,5-dihydroxy-4a,8-dimethyl-3,4,5,6,7,8-hexahydro-2H-naphthalen-2-yl]prop-2-enoic acid
• SMILES (Canonical): CC1CCC(C2(C1=CC(CC2O)C(=C)C(=O)O)C)O
• SMILES (Isomeric): C[C@H]1CC[C@H]([C@]2(C1=C[C@@H](C[C@@H]2O)C(=C)C(=O)O)C)O
• InChI: InChI=1S/C15H22O4/c1-8-4-5-12(16)15(3)11(8)6-10(7-13(15)17)9(2)14(18)19/h6,8,10,12-13,16-17H,2,4-5,7H2,1,3H3,(H,18,19)/t8-,10-,12+,13-,15+/m0/s1
• InChI Key: FLFLTGYDHAHKPY-UHVKOZFHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.73
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9848	98.48%
Caco-2	+	0.6009	60.09%
Blood Brain Barrier	-	0.5473	54.73%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7080	70.80%
OATP2B1 inhibitior	-	0.8566	85.66%
OATP1B1 inhibitior	+	0.9057	90.57%
OATP1B3 inhibitior	-	0.2902	29.02%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6327	63.27%
BSEP inhibitior	-	0.9716	97.16%
P-glycoprotein inhibitior	-	0.9405	94.05%
P-glycoprotein substrate	-	0.7853	78.53%
CYP3A4 substrate	+	0.5922	59.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8817	88.17%
CYP3A4 inhibition	-	0.7966	79.66%
CYP2C9 inhibition	-	0.8692	86.92%
CYP2C19 inhibition	-	0.9098	90.98%
CYP2D6 inhibition	-	0.9289	92.89%
CYP1A2 inhibition	-	0.8359	83.59%
CYP2C8 inhibition	-	0.8045	80.45%
CYP inhibitory promiscuity	-	0.9334	93.34%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6033	60.33%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9038	90.38%
Skin irritation	+	0.5798	57.98%
Skin corrosion	-	0.9055	90.55%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7082	70.82%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.6125	61.25%
skin sensitisation	-	0.6677	66.77%
Respiratory toxicity	-	0.5778	57.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.5999	59.99%
Acute Oral Toxicity (c)	I	0.5000	50.00%
Estrogen receptor binding	+	0.6823	68.23%
Androgen receptor binding	-	0.6716	67.16%
Thyroid receptor binding	-	0.5108	51.08%
Glucocorticoid receptor binding	+	0.5427	54.27%
Aromatase binding	+	0.6381	63.81%
PPAR gamma	-	0.5392	53.92%
Honey bee toxicity	-	0.8519	85.19%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6074	60.74%
Fish aquatic toxicity	+	0.9915	99.15%

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	95.87%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.23%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.81%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	85.39%	91.19%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	84.50%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.91%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.78%	92.94%

Plants that contains it

• Laggera crispata

Cross-Links

• PubChem: 10849383
• LOTUS: LTS0162536
• wikiData: Q104997027