(4S)-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-6-oxocyclohexene-1-carboxylic acid

Details

• Internal ID: 533388e8-1905-4eeb-8774-674feb499260
• Taxonomy: Benzenoids > Phenols > 1-hydroxy-2-unsubstituted benzenoids
• IUPAC Name: (4S)-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-6-oxocyclohexene-1-carboxylic acid
• SMILES (Canonical): C1C(CC(=O)C(=C1CCC2=CC=C(C=C2)O)C(=O)O)O
• SMILES (Isomeric): C1[C@@H](CC(=O)C(=C1CCC2=CC=C(C=C2)O)C(=O)O)O
• InChI: InChI=1S/C15H16O5/c16-11-5-2-9(3-6-11)1-4-10-7-12(17)8-13(18)14(10)15(19)20/h2-3,5-6,12,16-17H,1,4,7-8H2,(H,19,20)/t12-/m0/s1
• InChI Key: DWEBKCDBKMCKDE-LBPRGKRZSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28 g/mol
• Exact Mass: 276.09977361 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.43
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9558	95.58%
Caco-2	+	0.5290	52.90%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.9133	91.33%
OATP2B1 inhibitior	-	0.7165	71.65%
OATP1B1 inhibitior	+	0.8907	89.07%
OATP1B3 inhibitior	+	0.9421	94.21%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5300	53.00%
P-glycoprotein inhibitior	-	0.9487	94.87%
P-glycoprotein substrate	-	0.7616	76.16%
CYP3A4 substrate	-	0.5664	56.64%
CYP2C9 substrate	-	0.7656	76.56%
CYP2D6 substrate	-	0.8565	85.65%
CYP3A4 inhibition	-	0.5190	51.90%
CYP2C9 inhibition	-	0.7632	76.32%
CYP2C19 inhibition	-	0.6672	66.72%
CYP2D6 inhibition	-	0.9093	90.93%
CYP1A2 inhibition	-	0.8753	87.53%
CYP2C8 inhibition	-	0.6695	66.95%
CYP inhibitory promiscuity	-	0.8015	80.15%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8039	80.39%
Carcinogenicity (trinary)	Non-required	0.6485	64.85%
Eye corrosion	-	0.9887	98.87%
Eye irritation	+	0.8604	86.04%
Skin irritation	-	0.7009	70.09%
Skin corrosion	-	0.9698	96.98%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5637	56.37%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.6689	66.89%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6257	62.57%
Acute Oral Toxicity (c)	III	0.5499	54.99%
Estrogen receptor binding	+	0.7693	76.93%
Androgen receptor binding	+	0.6709	67.09%
Thyroid receptor binding	-	0.6725	67.25%
Glucocorticoid receptor binding	+	0.5408	54.08%
Aromatase binding	+	0.6872	68.72%
PPAR gamma	+	0.7540	75.40%
Honey bee toxicity	-	0.8273	82.73%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.7217	72.17%
Fish aquatic toxicity	+	0.9922	99.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.31%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.70%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.90%	91.11%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.42%	93.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	87.80%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.37%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.38%	95.56%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.27%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.22%	94.45%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.94%	91.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.66%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.22%	95.89%

Plants that contains it

• Conocephalum conicum
• Marchantia polymorpha

Cross-Links

• PubChem: 100988753
• NPASS: NPC195583
• LOTUS: LTS0093898
• wikiData: Q104393498