Malonyl-cis-shisonin

Details

• Internal ID: 88d5afb9-5f55-40b4-ae79-6cd0717591f9
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanidin 3-O-p-coumaroyl glycosides > Anthocyanidin 3-O-6-p-coumaroyl glycosides
• IUPAC Name: 3-[[(2R,3S,4S,5R,6S)-6-[2-(3,4-dihydroxyphenyl)-7-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[3-(4-hydroxyphenyl)prop-2-enoyloxymethyl]oxan-2-yl]oxychromenylium-5-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid
• SMILES (Canonical): C1=CC(=CC=C1C=CC(=O)OCC2C(C(C(C(O2)OC3=C([O+]=C4C=C(C=C(C4=C3)OC5C(C(C(C(O5)COC(=O)CC(=O)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C=CC(=O)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C([O+]=C4C=C(C=C(C4=C3)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)CC(=O)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O)O)O)O
• InChI: InChI=1S/C39H38O21/c40-18-5-1-16(2-6-18)3-8-29(46)54-14-26-31(48)34(51)36(53)39(60-26)58-25-12-20-23(56-37(25)17-4-7-21(42)22(43)9-17)10-19(41)11-24(20)57-38-35(52)33(50)32(49)27(59-38)15-55-30(47)13-28(44)45/h1-12,26-27,31-36,38-39,48-53H,13-15H2,(H4-,40,41,42,43,44,45,46)/p+1/t26-,27-,31-,32-,33+,34+,35-,36-,38-,39-/m1/s1
• InChI Key: HCZDGTUAMVKZNE-KMKFZPLVSA-O
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₃₉O₂₁+
• Molecular Weight: 843.70 g/mol
• Exact Mass: 843.19838325 g/mol
• Topological Polar Surface Area (TPSA): 330.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.15
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 13

Synonyms

• Malonyl-cis-shisonin
• 5-[[6-O-(Carboxyacetyl)-beta-D-glucopyranosyl]oxy]-7-hydroxy-2-(3,4-dihydroxyphenyl)-3-[[6-O-[3-(4-hydroxyphenyl)acryloyl]-beta-D-glucopyranosyl]oxy]-1-benzopyrylium

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6906	69.06%
Caco-2	-	0.8818	88.18%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Nucleus	0.4731	47.31%
OATP2B1 inhibitior	-	0.7088	70.88%
OATP1B1 inhibitior	+	0.8893	88.93%
OATP1B3 inhibitior	+	0.9503	95.03%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7955	79.55%
P-glycoprotein inhibitior	+	0.7195	71.95%
P-glycoprotein substrate	-	0.5671	56.71%
CYP3A4 substrate	+	0.6673	66.73%
CYP2C9 substrate	-	0.7946	79.46%
CYP2D6 substrate	-	0.8616	86.16%
CYP3A4 inhibition	-	0.9074	90.74%
CYP2C9 inhibition	-	0.9133	91.33%
CYP2C19 inhibition	-	0.8472	84.72%
CYP2D6 inhibition	-	0.9014	90.14%
CYP1A2 inhibition	-	0.9017	90.17%
CYP2C8 inhibition	+	0.8898	88.98%
CYP inhibitory promiscuity	-	0.9071	90.71%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6135	61.35%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9041	90.41%
Skin irritation	-	0.8197	81.97%
Skin corrosion	-	0.9482	94.82%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7775	77.75%
Micronuclear	+	0.6959	69.59%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.8681	86.81%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8695	86.95%
Acute Oral Toxicity (c)	III	0.4917	49.17%
Estrogen receptor binding	+	0.7549	75.49%
Androgen receptor binding	+	0.6845	68.45%
Thyroid receptor binding	+	0.5315	53.15%
Glucocorticoid receptor binding	+	0.5576	55.76%
Aromatase binding	+	0.5442	54.42%
PPAR gamma	+	0.6979	69.79%
Honey bee toxicity	-	0.7310	73.10%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9744	97.44%

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	99.55%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.23%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.97%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.45%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	95.20%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	94.45%	99.15%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.27%	99.17%
CHEMBL3194	P02766	Transthyretin	93.06%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.90%	96.09%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	88.81%	83.00%
CHEMBL2581	P07339	Cathepsin D	87.14%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.45%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.74%	91.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.57%	89.62%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.10%	95.83%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	84.05%	97.31%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.99%	95.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.53%	86.92%
CHEMBL3401	O75469	Pregnane X receptor	81.02%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.40%	97.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.20%	85.31%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.10%	94.33%

Plants that contains it

• Aconitum fischeri
• Apocynum androsaemifolium
• Espeletia grandiflora
• Huperzia yunnanensis
• Hyacinthus orientalis
• Lagascea mollis
• Perilla frutescens
• Pulmonaria mollis
• Rosa rugosa
• Rumex obtusifolius
• Tetracera alnifolia

Cross-Links

• PubChem: 101586992
• NPASS: NPC295990