Malonylgenistin

Details

• Internal ID: 40167ead-266c-4961-9892-91cf15af3009
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]propanoic acid
• SMILES (Canonical): C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)OC4C(C(C(C(O4)COC(=O)CC(=O)O)O)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)COC(=O)CC(=O)O)O)O)O)O
• InChI: InChI=1S/C24H22O13/c25-11-3-1-10(2-4-11)13-8-34-15-6-12(5-14(26)19(15)20(13)30)36-24-23(33)22(32)21(31)16(37-24)9-35-18(29)7-17(27)28/h1-6,8,16,21-26,31-33H,7,9H2,(H,27,28)/t16-,21-,22+,23-,24-/m1/s1
• InChI Key: FRAUJUKWSKMNJY-RSEYPYQYSA-N
• Popularity: 13 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₂O₁₃
• Molecular Weight: 518.40 g/mol
• Exact Mass: 518.10604075 g/mol
• Topological Polar Surface Area (TPSA): 210.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.08
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• 6''-O-MALONYLGENISTIN
• 51011-05-3
• Genistin Malonate
• Genistin 6''-O-Malonate
• 6-O-Malonylgenistin"
• 7-O-Glucosyl-6''-malonyl Genistein
• 2AUB85VT2K
• CHEBI:80372
• 3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]propanoic acid
• Malonyl genistin (constituent of soy isoflavones) [DSC]
• malonyl genistin
• 6''-Malonylgenistin
• 5-Hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl 6-O-(carboxylatoacetyl)hexopyranoside
• Malonyl-genistin
• 6-O-Malonylgenistin
• UNII-2AUB85VT2K
• MEGxp0_000226
• CHEMBL3426722
• ACon0_001356
• 6"-O-Malonylgenistin, Free Acid
• FRAUJUKWSKMNJY-RSEYPYQYSA-N
• DTXSID201316854
• HY-N0917
• CS-4241
• MS-29612
• Genistein-7-o-beta-D-glucosyl-6''-o-malonate
• genistein 7-O-beta-D-glucoside 6''-O-malonate
• Genistein 7-O-beta-d-glucoside-6''-O-malonate
• Q27149379
• GENISTEIN-7-O-.BETA.-D-GLUCOSYL-6''-O-MALONATE
• 5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 6-O-(carboxyacetyl)-beta-D-glucopyranoside
• PROPANEDIOIC ACID, 6'-ESTER WITH 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-5-HYDROXY-3-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
• Propanedioic acid, 6'-ester with 7-(beta-D-glucopyranosyloxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5156	51.56%
Caco-2	-	0.9140	91.40%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5919	59.19%
OATP2B1 inhibitior	-	0.5543	55.43%
OATP1B1 inhibitior	+	0.9309	93.09%
OATP1B3 inhibitior	+	0.9243	92.43%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.6137	61.37%
P-glycoprotein inhibitior	-	0.4533	45.33%
P-glycoprotein substrate	-	0.8004	80.04%
CYP3A4 substrate	+	0.6262	62.62%
CYP2C9 substrate	+	0.5675	56.75%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	-	0.8731	87.31%
CYP2C9 inhibition	-	0.9393	93.93%
CYP2C19 inhibition	-	0.9222	92.22%
CYP2D6 inhibition	-	0.9352	93.52%
CYP1A2 inhibition	-	0.9262	92.62%
CYP2C8 inhibition	+	0.7393	73.93%
CYP inhibitory promiscuity	-	0.9340	93.40%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6855	68.55%
Eye corrosion	-	0.9925	99.25%
Eye irritation	-	0.8858	88.58%
Skin irritation	-	0.8213	82.13%
Skin corrosion	-	0.9590	95.90%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5116	51.16%
Micronuclear	+	0.7118	71.18%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.9103	91.03%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.7619	76.19%
Acute Oral Toxicity (c)	III	0.4846	48.46%
Estrogen receptor binding	+	0.8193	81.93%
Androgen receptor binding	+	0.6667	66.67%
Thyroid receptor binding	+	0.5213	52.13%
Glucocorticoid receptor binding	+	0.6215	62.15%
Aromatase binding	+	0.6254	62.54%
PPAR gamma	+	0.7532	75.32%
Honey bee toxicity	-	0.8193	81.93%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6650	66.50%
Fish aquatic toxicity	+	0.9497	94.97%

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	99.00%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.88%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.63%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.15%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.17%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.70%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.44%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	88.44%	86.92%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.38%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.81%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.41%	85.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.13%	95.83%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.66%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.05%	97.09%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.44%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.36%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	81.24%	92.50%
CHEMBL3194	P02766	Transthyretin	81.18%	90.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.75%	91.71%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.45%	95.78%
CHEMBL226	P30542	Adenosine A1 receptor	80.29%	95.93%

Plants that contains it

• Glycine max
• Maackia amurensis
• Murraya exotica
• Murraya paniculata
• Pueraria montana var. lobata
• Trifolium pratense
• Trifolium subterraneum

Cross-Links

• PubChem: 15934091
• NPASS: NPC176259
• LOTUS: LTS0050574
• wikiData: Q27149379