(2R,4S)-2-(4-hydroxy-3-methylphenyl)-3,4-dihydro-2H-chromene-4,5,7-triol

Details

• Internal ID: e87adadb-9c7d-4a7b-94cc-ede62b94aa87
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavan-4-ols
• IUPAC Name: (2R,4S)-2-(4-hydroxy-3-methylphenyl)-3,4-dihydro-2H-chromene-4,5,7-triol
• SMILES (Canonical): CC1=C(C=CC(=C1)C2CC(C3=C(C=C(C=C3O2)O)O)O)O
• SMILES (Isomeric): CC1=C(C=CC(=C1)[C@H]2C[C@@H](C3=C(C=C(C=C3O2)O)O)O)O
• InChI: InChI=1S/C16H16O5/c1-8-4-9(2-3-11(8)18)14-7-13(20)16-12(19)5-10(17)6-15(16)21-14/h2-6,13-14,17-20H,7H2,1H3/t13-,14+/m0/s1
• InChI Key: VSTNKEFYHIVZJZ-UONOGXRCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₆O₅
• Molecular Weight: 288.29 g/mol
• Exact Mass: 288.09977361 g/mol
• Topological Polar Surface Area (TPSA): 90.20 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.67
• H-Bond Acceptor: 5
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9388	93.88%
Caco-2	+	0.5479	54.79%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6312	63.12%
OATP2B1 inhibitior	-	0.5915	59.15%
OATP1B1 inhibitior	+	0.9343	93.43%
OATP1B3 inhibitior	+	0.9339	93.39%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.8154	81.54%
P-glycoprotein inhibitior	-	0.9453	94.53%
P-glycoprotein substrate	-	0.9053	90.53%
CYP3A4 substrate	+	0.5087	50.87%
CYP2C9 substrate	-	0.7786	77.86%
CYP2D6 substrate	+	0.5594	55.94%
CYP3A4 inhibition	+	0.6107	61.07%
CYP2C9 inhibition	+	0.6864	68.64%
CYP2C19 inhibition	+	0.6969	69.69%
CYP2D6 inhibition	-	0.7537	75.37%
CYP1A2 inhibition	+	0.7078	70.78%
CYP2C8 inhibition	-	0.5619	56.19%
CYP inhibitory promiscuity	+	0.6381	63.81%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5417	54.17%
Eye corrosion	-	0.9923	99.23%
Eye irritation	-	0.5240	52.40%
Skin irritation	-	0.6123	61.23%
Skin corrosion	-	0.8723	87.23%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3969	39.69%
Micronuclear	+	0.7359	73.59%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8725	87.25%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.6119	61.19%
Acute Oral Toxicity (c)	III	0.3763	37.63%
Estrogen receptor binding	-	0.4755	47.55%
Androgen receptor binding	+	0.6555	65.55%
Thyroid receptor binding	+	0.7690	76.90%
Glucocorticoid receptor binding	+	0.6679	66.79%
Aromatase binding	+	0.6483	64.83%
PPAR gamma	+	0.7242	72.42%
Honey bee toxicity	-	0.9300	93.00%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.7598	75.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.41%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	92.77%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.31%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.99%	99.15%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.84%	93.40%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.23%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.36%	95.56%
CHEMBL4208	P20618	Proteasome component C5	87.01%	90.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.25%	96.09%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	85.09%	91.79%
CHEMBL1929	P47989	Xanthine dehydrogenase	83.91%	96.12%

Plants that contains it

• Limonium bicolor

Cross-Links

• PubChem: 162980072
• LOTUS: LTS0088235
• wikiData: Q105292494