(2R,3S)-2-(3,4-dihydroxyphenyl)-3,7,8-trihydroxy-2,3-dihydrochromen-4-one

Details

• Internal ID: 2e8a2df3-7ebc-4a35-83a9-0dbf5621d4fc
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones > Flavanonols
• IUPAC Name: (2R,3S)-2-(3,4-dihydroxyphenyl)-3,7,8-trihydroxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2C(C(=O)C3=C(O2)C(=C(C=C3)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1[C@@H]2[C@@H](C(=O)C3=C(O2)C(=C(C=C3)O)O)O)O)O
• InChI: InChI=1S/C15H12O7/c16-8-3-1-6(5-10(8)18)14-13(21)11(19)7-2-4-9(17)12(20)15(7)22-14/h1-5,13-14,16-18,20-21H/t13-,14-/m1/s1
• InChI Key: MBLFTUVXKRACOC-ZIAGYGMSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₇
• Molecular Weight: 304.25 g/mol
• Exact Mass: 304.05830272 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.19
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9569	95.69%
Caco-2	-	0.9385	93.85%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7742	77.42%
OATP2B1 inhibitior	-	0.6865	68.65%
OATP1B1 inhibitior	+	0.9121	91.21%
OATP1B3 inhibitior	+	0.9902	99.02%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9231	92.31%
P-glycoprotein inhibitior	-	0.9078	90.78%
P-glycoprotein substrate	-	0.9637	96.37%
CYP3A4 substrate	-	0.5434	54.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7351	73.51%
CYP3A4 inhibition	-	0.7054	70.54%
CYP2C9 inhibition	+	0.8949	89.49%
CYP2C19 inhibition	-	0.6965	69.65%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	+	0.9249	92.49%
CYP2C8 inhibition	-	0.7851	78.51%
CYP inhibitory promiscuity	-	0.5409	54.09%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5926	59.26%
Eye corrosion	-	0.9890	98.90%
Eye irritation	+	0.9564	95.64%
Skin irritation	+	0.6100	61.00%
Skin corrosion	-	0.9613	96.13%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8192	81.92%
Micronuclear	+	0.9400	94.00%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8006	80.06%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6297	62.97%
Acute Oral Toxicity (c)	II	0.7187	71.87%
Estrogen receptor binding	+	0.5363	53.63%
Androgen receptor binding	+	0.7043	70.43%
Thyroid receptor binding	+	0.6561	65.61%
Glucocorticoid receptor binding	+	0.8052	80.52%
Aromatase binding	+	0.6352	63.52%
PPAR gamma	+	0.5563	55.63%
Honey bee toxicity	-	0.8756	87.56%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9311	93.11%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.86%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.76%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.63%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.53%	89.00%
CHEMBL2581	P07339	Cathepsin D	88.15%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.70%	99.15%
CHEMBL3194	P02766	Transthyretin	83.66%	90.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.08%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	81.10%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.86%	97.09%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.10%	93.40%

Plants that contains it

• Acacia melanoxylon

Cross-Links

• PubChem: 163083455
• LOTUS: LTS0078404
• wikiData: Q105160835