Apigenin 7-(6''-malonylglucoside)

Details

• Internal ID: 605e6941-a8a7-4472-8762-4515e353f329
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]propanoic acid
• InChI: InChI=1S/C24H22O13/c25-11-3-1-10(2-4-11)15-7-14(27)20-13(26)5-12(6-16(20)36-15)35-24-23(33)22(32)21(31)17(37-24)9-34-19(30)8-18(28)29/h1-7,17,21-26,31-33H,8-9H2,(H,28,29)/t17-,21-,22+,23-,24-/m1/s1
• InChI Key: JXWAQRJFONLTSI-ASDZUOGYSA-N
• Popularity: 6 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: -0.30
• Atomic LogP (AlogP): 0.08
• H-Bond Acceptor: 12
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• Apigenin 7-O-malonylglucoside
• AOF5Z3UWMW
• Apigenin 7-O-(6''-O-malonylglucoside)
• Apigenin 7-O-(6-malonyl-beta-D-glucoside)
• C10020
• Apigenin 7-(6''-malonylglucoside)
• 3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]propanoic acid
• Apigenin 7-O-(6 inverted exclamation mark -O-malonyl)-|A-D-glucoside
• Apigenin 7-O-(6-O-malonylglucoside)
• AC1NQYPG
• UNII-AOF5Z3UWMW
• 7-MAG
• Malonyl apigenin 7-O-glucoside
• CHEBI:166640
• HY-N2496
• AKOS040760142
• FS-8271
• CS-0022767
• APIGENIN 7-O-(6''-MALONYL)-.BETA.-D-GLUCOPYRANOSIDE
• 3-oxo-3-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-yl]methoxy]propanoic acid
• 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(CARBOXYACETYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-5-HYDROXY-2-(4-HYDROXYPHENYL)-
• 7-((6-O-(CARBOXYACETYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
• PROPANEDIOIC ACID, 6'-ESTER WITH 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
• Propanedioic acid, 6'-ester with 7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5510	55.10%
Caco-2	-	0.9109	91.09%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6401	64.01%
OATP2B1 inhibitior	-	0.5498	54.98%
OATP1B1 inhibitior	+	0.9377	93.77%
OATP1B3 inhibitior	+	0.9409	94.09%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7187	71.87%
P-glycoprotein inhibitior	-	0.4611	46.11%
P-glycoprotein substrate	-	0.7145	71.45%
CYP3A4 substrate	+	0.5955	59.55%
CYP2C9 substrate	+	0.5675	56.75%
CYP2D6 substrate	-	0.8699	86.99%
CYP3A4 inhibition	-	0.8793	87.93%
CYP2C9 inhibition	-	0.9538	95.38%
CYP2C19 inhibition	-	0.9360	93.60%
CYP2D6 inhibition	-	0.9354	93.54%
CYP1A2 inhibition	-	0.9400	94.00%
CYP2C8 inhibition	+	0.7766	77.66%
CYP inhibitory promiscuity	-	0.9331	93.31%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6342	63.42%
Eye corrosion	-	0.9920	99.20%
Eye irritation	-	0.8735	87.35%
Skin irritation	-	0.8209	82.09%
Skin corrosion	-	0.9598	95.98%
Ames mutagenesis	+	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5158	51.58%
Micronuclear	+	0.6918	69.18%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.9230	92.30%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9149	91.49%
Acute Oral Toxicity (c)	III	0.5344	53.44%
Estrogen receptor binding	+	0.7848	78.48%
Androgen receptor binding	+	0.6905	69.05%
Thyroid receptor binding	-	0.5152	51.52%
Glucocorticoid receptor binding	+	0.6445	64.45%
Aromatase binding	+	0.5980	59.80%
PPAR gamma	+	0.7254	72.54%
Honey bee toxicity	-	0.7778	77.78%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.7150	71.50%
Fish aquatic toxicity	+	0.9354	93.54%

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	99.35%	91.11%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	95.70%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.69%	85.14%
CHEMBL2581	P07339	Cathepsin D	95.22%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.11%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.97%	94.00%
CHEMBL220	P22303	Acetylcholinesterase	92.92%	94.45%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.38%	95.64%
CHEMBL3194	P02766	Transthyretin	88.98%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.55%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.61%	90.71%
CHEMBL3401	O75469	Pregnane X receptor	86.39%	94.73%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	85.17%	89.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.85%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	84.16%	91.49%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.74%	86.92%
CHEMBL5255	O00206	Toll-like receptor 4	82.57%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.30%	97.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	81.28%	80.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.55%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.34%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.23%	96.09%

Plants that contains it

• Cynara cardunculus
• Monarda punctata
• Pueraria montana var. lobata

Cross-Links

• PubChem: 5281602
• LOTUS: LTS0057395
• wikiData: Q76285980