Genistein 7,4'-di-O-beta-D-glucopyranoside

Details

• Internal ID: ad8d9577-535b-4c6a-b8b5-490c09d57c75
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)OC4C(C(C(C(O4)CO)O)O)O)OC5C(C(C(C(O5)CO)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O
• InChI: InChI=1S/C27H30O15/c28-7-16-20(32)22(34)24(36)26(41-16)39-11-3-1-10(2-4-11)13-9-38-15-6-12(5-14(30)18(15)19(13)31)40-27-25(37)23(35)21(33)17(8-29)42-27/h1-6,9,16-17,20-30,32-37H,7-8H2/t16-,17-,20-,21-,22+,23+,24-,25-,26-,27-/m1/s1
• InChI Key: OUJDQONJYHNTDX-UMUUNPGWSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₅
• Molecular Weight: 594.50 g/mol
• Exact Mass: 594.15847025 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -2.48
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

• Genistein 7,4'-di-O-beta-D-glucopyranoside
• Genistein 7,4'-di-O-|A-D-glucoside
• Genistein 7,4'-di-O-glucoside
• 5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• Genistein 4'-O,7-diglucoside
• HY-N5103
• AKOS040760419
• Genistein 7,4'-di-O-??-D-glucoside
• Genistein 7,4'-di-O-beta-D-glucoside
• CS-0032369
• E88672
• 5-hydroxy-7-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-3-(4-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)phenyl)-4h-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5736	57.36%
Caco-2	-	0.9122	91.22%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5848	58.48%
OATP2B1 inhibitior	+	0.5820	58.20%
OATP1B1 inhibitior	+	0.9598	95.98%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6512	65.12%
P-glycoprotein inhibitior	-	0.5141	51.41%
P-glycoprotein substrate	-	0.9265	92.65%
CYP3A4 substrate	+	0.5952	59.52%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9390	93.90%
CYP2C9 inhibition	-	0.9315	93.15%
CYP2C19 inhibition	-	0.9047	90.47%
CYP2D6 inhibition	-	0.9458	94.58%
CYP1A2 inhibition	-	0.9180	91.80%
CYP2C8 inhibition	+	0.6109	61.09%
CYP inhibitory promiscuity	-	0.7526	75.26%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6848	68.48%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8836	88.36%
Skin irritation	-	0.8255	82.55%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7133	71.33%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9132	91.32%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.5904	59.04%
Acute Oral Toxicity (c)	IV	0.4763	47.63%
Estrogen receptor binding	+	0.8279	82.79%
Androgen receptor binding	+	0.6256	62.56%
Thyroid receptor binding	+	0.5666	56.66%
Glucocorticoid receptor binding	-	0.4793	47.93%
Aromatase binding	+	0.5883	58.83%
PPAR gamma	+	0.7962	79.62%
Honey bee toxicity	-	0.7540	75.40%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.7958	79.58%

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	99.14%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.78%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.54%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.26%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.69%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	92.40%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.19%	97.09%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.95%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.00%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.64%	99.17%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.52%	95.78%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.54%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.32%	96.09%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.71%	97.28%
CHEMBL3194	P02766	Transthyretin	81.77%	90.71%
CHEMBL4208	P20618	Proteasome component C5	81.54%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.93%	95.89%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.26%	90.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.24%	91.71%

Plants that contains it

• Calicotome villosa
• Genista pichisermolliana
• Ipomoea muricata
• Lupinus luteus
• Lupinus polyphyllus
• Maackia amurensis
• Magnolia coco
• Ocimum basilicum
• Pinus hartwegii
• Styphnolobium japonicum

Cross-Links

• PubChem: 91431845
• NPASS: NPC79765
• LOTUS: LTS0269579
• wikiData: Q104667515