6''-O-Malonylglycitin

Details

• Internal ID: 5d0e5c60-634e-4bb6-8ed1-4a2021439f60
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[3-(4-hydroxyphenyl)-6-methoxy-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]propanoic acid
• SMILES (Canonical): COC1=C(C=C2C(=C1)C(=O)C(=CO2)C3=CC=C(C=C3)O)OC4C(C(C(C(O4)COC(=O)CC(=O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C(=O)C(=CO2)C3=CC=C(C=C3)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)COC(=O)CC(=O)O)O)O)O
• InChI: InChI=1S/C25H24O13/c1-34-16-6-13-15(35-9-14(21(13)30)11-2-4-12(26)5-3-11)7-17(16)37-25-24(33)23(32)22(31)18(38-25)10-36-20(29)8-19(27)28/h2-7,9,18,22-26,31-33H,8,10H2,1H3,(H,27,28)/t18-,22-,23+,24-,25-/m1/s1
• InChI Key: OWMHCYFEIJPHFB-GOZZSVHWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₄O₁₃
• Molecular Weight: 532.40 g/mol
• Exact Mass: 532.12169082 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 0.38
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

• 6''-O-MALONYLGLYCITIN
• Glycitin 6''-O-Malonate
• Glycitein 6''-O-Malonylglucoside
• 7625LXB9M8
• UNII-7625LXB9M8
• 3-(4-Hydroxyphenyl)-6-methoxy-4-oxo-4H-chromen-8-yl 6-O-(carboxyacetyl)-beta-D-glucopyranoside
• 3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[3-(4-hydroxyphenyl)-6-methoxy-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]propanoic acid
• 4H-1-Benzopyran-4-one, 7-((6-O-(2-carboxyacetyl)-beta-D-glucopyranosyl)oxy)-3-(4-hydroxyphenyl)-6-methoxy-
• malonyl glycitin
• Malonyl-glycitin
• 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(2-CARBOXYACETYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-3-(4-HYDROXYPHENYL)-6-METHOXY-
• 4H-1-Benzopyran-4-one, 7-[[6-O-(2-carboxyacetyl)-.beta.-D-glucopyranosyl]oxy]-3-(4-hydroxyphenyl)-6-methoxy-
• CHEBI:80374
• DTXSID701314722
• Q27149386
• MALONYL GLYCITIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC]
• 3-(4-hydroxyphenyl)-6-methoxy-4-oxo-4H-1-benzopyran-7-yl 6-O-(carboxyacetyl)-beta-D-glucopyranoside
• 3-(4-HYDROXYPHENYL)-6-METHOXY-4-OXO-4H-CHROMEN-8-YL 6-O-(CARBOXYACETYL)-.BETA.-D-GLUCOPYRANOSIDE
• 3-oxo-3-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-6-methoxy-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl]methoxy}propanoic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4650	46.50%
Caco-2	-	0.8917	89.17%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6150	61.50%
OATP2B1 inhibitior	-	0.8382	83.82%
OATP1B1 inhibitior	+	0.8929	89.29%
OATP1B3 inhibitior	+	0.9628	96.28%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.6206	62.06%
P-glycoprotein inhibitior	+	0.6419	64.19%
P-glycoprotein substrate	-	0.5773	57.73%
CYP3A4 substrate	+	0.6529	65.29%
CYP2C9 substrate	-	0.6285	62.85%
CYP2D6 substrate	-	0.8563	85.63%
CYP3A4 inhibition	-	0.8782	87.82%
CYP2C9 inhibition	-	0.9310	93.10%
CYP2C19 inhibition	-	0.9222	92.22%
CYP2D6 inhibition	-	0.9310	93.10%
CYP1A2 inhibition	-	0.9104	91.04%
CYP2C8 inhibition	+	0.7675	76.75%
CYP inhibitory promiscuity	-	0.9238	92.38%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6500	65.00%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9342	93.42%
Skin irritation	-	0.8282	82.82%
Skin corrosion	-	0.9516	95.16%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4568	45.68%
Micronuclear	+	0.6918	69.18%
Hepatotoxicity	-	0.5497	54.97%
skin sensitisation	-	0.9297	92.97%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.8681	86.81%
Acute Oral Toxicity (c)	III	0.6607	66.07%
Estrogen receptor binding	+	0.8505	85.05%
Androgen receptor binding	+	0.7152	71.52%
Thyroid receptor binding	+	0.5485	54.85%
Glucocorticoid receptor binding	+	0.7543	75.43%
Aromatase binding	+	0.6152	61.52%
PPAR gamma	+	0.7282	72.82%
Honey bee toxicity	-	0.8412	84.12%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6749	67.49%
Fish aquatic toxicity	+	0.9093	90.93%

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	98.60%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.79%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.77%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.48%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.26%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.66%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.36%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.99%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.76%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.80%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	86.56%	92.50%
CHEMBL2535	P11166	Glucose transporter	84.58%	98.75%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.93%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.54%	95.83%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.25%	90.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.67%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	82.53%	95.64%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.52%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	82.39%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.80%	99.23%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	80.85%	86.92%

Plants that contains it

• Glycine max
• Murraya exotica
• Murraya paniculata

Cross-Links

• PubChem: 23724657
• NPASS: NPC273687
• LOTUS: LTS0261337
• wikiData: Q27149386