Genistein 7-O-beta-D-glucoside

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

Top

Internal ID	1663f022-6c3d-4af8-ba11-6e91b07c7718
Taxonomy	Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
IUPAC Name	5-hydroxy-3-(4-hydroxyphenyl)-7-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
SMILES (Canonical)	C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)OC4C(C(C(C(O4)CO)O)O)O)O
SMILES (Isomeric)	C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)OC4C(C(C(C(O4)CO)O)O)O)O
InChI	InChI=1S/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-5-13(24)16-14(6-11)29-8-12(17(16)25)9-1-3-10(23)4-2-9/h1-6,8,15,18-24,26-28H,7H2
InChI Key	ZCOLJUOHXJRHDI-UHFFFAOYSA-N
Popularity	7 references in papers

Physical and Chemical Properties

Top

Molecular Formula	C₂₁H₂₀O₁₀
Molecular Weight	432.40 g/mol
Exact Mass	432.10564683 g/mol
Topological Polar Surface Area (TPSA)	166.00 Å²
XlogP	0.90
Atomic LogP (AlogP)	0.05
H-Bond Acceptor	10
H-Bond Donor	6
Rotatable Bonds	4

Synonyms

Top

Genistein glucoside

Genistein-7-glucoside

NSC5112

Genistein 7-O-.beta.-D-glucoside

Genistein, 7-.beta.-D-glucopyranoside

5-hydroxy-3-(4-hydroxyphenyl)-7-[[3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-1-benzopyran-4-one

NSC-5112

4H-1-Benzopyran-4-one, 7-(.beta.-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-

4',5,7-Trihydroxyisoflavone 7-glucoside

Genistin (8CI)

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

Top

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9370	93.70%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.5888	58.88%
OATP1B1 inhibitior	+	0.9521	95.21%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5394	53.94%
P-glycoprotein inhibitior	-	0.8277	82.77%
P-glycoprotein substrate	-	0.9175	91.75%
CYP3A4 substrate	+	0.5951	59.51%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
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	+	0.6652	66.52%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.8281	82.81%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5316	53.16%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6946	69.46%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	+	0.4741	47.41%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7238	72.38%
Androgen receptor binding	+	0.7130	71.30%
Thyroid receptor binding	+	0.6096	60.96%
Glucocorticoid receptor binding	+	0.6300	63.00%
Aromatase binding	+	0.6456	64.56%
PPAR gamma	+	0.8322	83.22%
Honey bee toxicity	-	0.7440	74.40%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.8218	82.18%

Targets

Top

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	39810.7 nM	Potency	via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	5623.4 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	31622.8 nM	Potency	via CMAUP
CHEMBL1293294	P51151	Ras-related protein Rab-9A	5623.4 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	25118.9 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.95%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.10%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.38%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.51%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.25%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	91.75%	86.92%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.01%	96.21%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.86%	97.09%
CHEMBL242	Q92731	Estrogen receptor beta	88.57%	98.35%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.49%	95.78%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.85%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	87.34%	95.64%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.04%	99.17%
CHEMBL3194	P02766	Transthyretin	85.31%	90.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	84.58%	91.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.09%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.45%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.95%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.32%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	80.87%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.63%	95.83%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.12%	90.71%

Plants that contains it

Top

Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Flemingia macrophylla

Flemingia paniculata

Genista ephedroides

Genista pichisermolliana

Genista sessilifolia

Glycine max

Iris spuria