(2S)-7-hydroxy-2-phenyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one

Details

• Internal ID: 668b093c-9e46-4b7b-8262-28e03eadbc8e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides
• IUPAC Name: (2S)-7-hydroxy-2-phenyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=C(C1=O)C(=CC(=C2)O)OC3C(C(C(C(O3)CO)O)O)O)C4=CC=CC=C4
• SMILES (Isomeric): C1[C@H](OC2=C(C1=O)C(=CC(=C2)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C4=CC=CC=C4
• InChI: InChI=1S/C21H22O9/c22-9-16-18(25)19(26)20(27)21(30-16)29-15-7-11(23)6-14-17(15)12(24)8-13(28-14)10-4-2-1-3-5-10/h1-7,13,16,18-23,25-27H,8-9H2/t13-,16+,18+,19-,20+,21+/m0/s1
• InChI Key: VFPGPPMQCHGMCT-ITSUVCJSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₉
• Molecular Weight: 418.40 g/mol
• Exact Mass: 418.12638228 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.28
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9215	92.15%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	-	0.6989	69.89%
OATP1B1 inhibitior	+	0.9323	93.23%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6026	60.26%
P-glycoprotein inhibitior	-	0.7023	70.23%
P-glycoprotein substrate	-	0.9052	90.52%
CYP3A4 substrate	+	0.5569	55.69%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8143	81.43%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	+	0.5409	54.09%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.9003	90.03%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.5130	51.30%
Human Ether-a-go-go-Related Gene inhibition	-	0.5594	55.94%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.7500	75.00%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.6176	61.76%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7779	77.79%
Androgen receptor binding	-	0.5126	51.26%
Thyroid receptor binding	+	0.5186	51.86%
Glucocorticoid receptor binding	+	0.5990	59.90%
Aromatase binding	+	0.7136	71.36%
PPAR gamma	+	0.8050	80.50%
Honey bee toxicity	-	0.7687	76.87%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5749	57.49%
Fish aquatic toxicity	+	0.8218	82.18%

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	99.21%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.23%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.16%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.14%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.94%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.22%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.50%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.34%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	85.85%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.04%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.01%	96.21%

Plants that contains it

• Prunus leveilleana

Cross-Links

• PubChem: 163050534
• LOTUS: LTS0266114
• wikiData: Q105285495