Malonylapiin

Details

• Internal ID: f44cb253-eb66-4607-bf49-a4e62eeace7d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 3-[[(2R,3S,4S,5R,6S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,4-dihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]-3-oxopropanoic acid
• InChI: InChI=1S/C29H30O17/c30-10-29(40)11-42-28(26(29)39)46-25-24(38)23(37)19(9-41-21(36)8-20(34)35)45-27(25)43-14-5-15(32)22-16(33)7-17(44-18(22)6-14)12-1-3-13(31)4-2-12/h1-7,19,23-28,30-32,37-40H,8-11H2,(H,34,35)/t19-,23-,24+,25-,26+,27-,28+,29-/m1/s1
• InChI Key: JNAHTYWPEQLJRT-CQRLEKJLSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₀O₁₇
• Molecular Weight: 650.50 g/mol
• Exact Mass: 650.14829948 g/mol
• Topological Polar Surface Area (TPSA): 268.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.46
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

• CHEBI:6664
• 3-[[(2R,3S,4S,5R,6S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,4-dihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyoxan-2-yl]methoxy]-3-oxopropanoic acid
• 3-(((2R,3S,4S,5R,6S)-5-((2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl)oxy-3,4-dihydroxy-6-(5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl)oxyoxan-2-yl)methoxy)-3-oxopropanoic acid
• 3-(((2R,3S,4S,5R,6S)-5-((2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl)oxy-3,4-dihydroxy-6-(5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-chromen-7-yl)oxy-tetrahydropyran-2-yl)methoxy)-3-oxo-propanoic acid
• 3-[[(2R,3S,4S,5R,6S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)tetrahydrofuran-2-yl]oxy-3,4-dihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-chromen-7-yl]oxy-tetrahydropyran-2-yl]methoxy]-3-oxo-propanoic acid
• RefChem:1088780
• C05622
• 6''-Malonylapiin
• 7-O-[beta-D-apiosyl-(1->2)-(6-malonyl-beta-D-glucoside)]
• AC1NQXM8
• Q27107294
• Apigenin 7-O-[beta-D-apiosyl-(1->2)-(6-malonyl-beta-D-glucoside)]
• 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7-yl 6-O-(carboxyacetyl)-2-O-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]-beta-D-glucopyranoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4604	46.04%
Caco-2	-	0.9047	90.47%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6537	65.37%
OATP2B1 inhibitior	-	0.7075	70.75%
OATP1B1 inhibitior	+	0.9198	91.98%
OATP1B3 inhibitior	+	0.9654	96.54%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8466	84.66%
P-glycoprotein inhibitior	+	0.6118	61.18%
P-glycoprotein substrate	+	0.5323	53.23%
CYP3A4 substrate	+	0.6874	68.74%
CYP2C9 substrate	-	0.6163	61.63%
CYP2D6 substrate	-	0.8706	87.06%
CYP3A4 inhibition	-	0.8388	83.88%
CYP2C9 inhibition	-	0.9233	92.33%
CYP2C19 inhibition	-	0.8624	86.24%
CYP2D6 inhibition	-	0.9192	91.92%
CYP1A2 inhibition	-	0.9244	92.44%
CYP2C8 inhibition	+	0.7618	76.18%
CYP inhibitory promiscuity	-	0.8837	88.37%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5247	52.47%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9060	90.60%
Skin irritation	-	0.8145	81.45%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6799	67.99%
Micronuclear	+	0.6359	63.59%
Hepatotoxicity	-	0.6875	68.75%
skin sensitisation	-	0.8937	89.37%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.9013	90.13%
Acute Oral Toxicity (c)	III	0.5334	53.34%
Estrogen receptor binding	+	0.8421	84.21%
Androgen receptor binding	+	0.6924	69.24%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5781	57.81%
Aromatase binding	+	0.6994	69.94%
PPAR gamma	+	0.7393	73.93%
Honey bee toxicity	-	0.7135	71.35%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6750	67.50%
Fish aquatic toxicity	+	0.8988	89.88%

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	99.75%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.78%	89.00%
CHEMBL220	P22303	Acetylcholinesterase	95.58%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.37%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.84%	99.15%
CHEMBL226	P30542	Adenosine A1 receptor	94.50%	95.93%
CHEMBL2581	P07339	Cathepsin D	94.12%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.09%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.76%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.21%	95.56%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.91%	86.92%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	88.77%	95.83%
CHEMBL340	P08684	Cytochrome P450 3A4	88.47%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.00%	95.89%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.79%	94.33%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	87.31%	89.23%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.17%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.96%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.08%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	85.24%	92.50%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	85.20%	80.33%
CHEMBL1951	P21397	Monoamine oxidase A	84.93%	91.49%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	84.18%	83.57%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.69%	97.28%
CHEMBL4530	P00488	Coagulation factor XIII	80.61%	96.00%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.54%	97.53%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.31%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.05%	99.17%

Plants that contains it

• Atroxima liberica
• Bergenia crassifolia
• Christisonia bicolor
• Convallaria majalis
• Corynanthe pachyceras
• Crotalaria orixensis
• Isodon angustifolius
• Lawsonia inermis
• Licaria brasiliensis
• Linum salsoloides
• Palafoxia texana
• Petroselinum crispum
• Sanguisorba officinalis
• Scutellaria sieberi
• Smilax bracteata
• Tynanthus panurensis
• Vepris nobilis

Cross-Links

• PubChem: 5280803
• NPASS: NPC72335
• LOTUS: LTS0121233
• wikiData: Q27107294