CALYCOSIN 7-O-beta-D-GLUCOSIDE

Details

• Internal ID: cc799888-8b03-4e02-848a-e89dc34f4011
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 3-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=COC3=C(C2=O)C=CC(=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C22H22O10/c1-29-15-5-2-10(6-14(15)24)13-9-30-16-7-11(3-4-12(16)18(13)25)31-22-21(28)20(27)19(26)17(8-23)32-22/h2-7,9,17,19-24,26-28H,8H2,1H3/t17-,19-,20+,21-,22-/m1/s1
• InChI Key: WACBUPFEGWUGPB-MIUGBVLSSA-N
• Popularity: 83 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₁₀
• Molecular Weight: 446.40 g/mol
• Exact Mass: 446.12129689 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.35
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• Calycosin-7-O-beta-D-glucoside
• Calycosin 7-O-glucoside
• calycosin-7-O-beta-D-glucopyranoside
• Calycosin 7-o-beta-D-glucoside
• Calycosin 7-O-glucopyranoside
• Calycosin-7-O-|A-D-glucoside
• UNII-247AW3A88C
• 247AW3A88C
• Calycosin 7-beta-D-glucopyranoside
• CALYCOSIN 7-O-BETA-D-GLUCOPYRANOSIDE
• CHEMBL3289608
• CHEBI:86512
• CALYCOSIN-7-O-B-D-GLUCOSIDE
• 3-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• 7,3'-Dihydroxy-4'-methoxyisoflavone-7-o-beta-D-glucoside
• 3',7-Dihydroxy-4'-methoxyisoflavone-7-beta-D-glucopyranoside
• Calycosin 7-O-glucopyranoside (constituent of astragalus) [DSC]
• Isoflavone, 3',7-dihydroxy-4'-methoxy-, 7-beta-D-glucopyranoside
• 4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-3-(3-hydroxy-4-methoxyphenyl)-
• CALYCOSIN 7-O-BETA-D-GLUCOPYRANOSIDE (USP-RS)
• CALYCOSIN 7-O-BETA-D-GLUCOPYRANOSIDE [USP-RS]
• Calycosin 7-glucoside
• 3'-Hydroxy-4'-methoxyisoflavone-7-O-beta-D-glucoside
• GLXC-13147
• HMS3886F16
• HY-N0520
• BDBM50021397
• MFCD08061493
• s9088
• AKOS015897094
• CCG-269192
• CS-3716
• AC-34486
• CALYCOSIN 7-O-.BETA.-D-GLUCOSIDE
• MS-28052
• CALYCOSIN 7-.BETA.-D-GLUCOPYRANOSIDE
• FT-0688328
• CALYCOSIN-7-O-.BETA.-D-GLUCOPYRANOSIDE
• Q-100930
• Q27159206
• Calycosin 7-O-glucopyranoside (constituent of astragalus)
• 7,3'-DIHYDROXY-4'-METHOXYISOFLAVONE-7-O-.BETA.-D-GLUCOSIDE
• 3',7-DIHYDROXY-4'-METHOXYISOFLAVONE-7-.BETA.-D-GLUCOPYRANOSIDE
• ISOFLAVONE, 3',7-DIHYDROXY-4'-METHOXY-, 7-.BETA.-D-GLUCOPYRANOSIDE
• 3-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-1-benzopyran-7-yl beta-D-glucopyranoside
• 3-(3-hydroxy-4-methoxy-phenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
• 3-(3-hydroxy-4-methoxyphenyl)-7-(((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-4h-chromen-4-one
• 4H-1-BENZOPYRAN-4-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-3-(3-HYDROXY-4-METHOXYPHENYL)-
• Calycosin-7-O-AfAE'A centa' notA inverted exclamation markAfasA'A|AfAE'Adaggeratrade markAfA centA centasA notA em leaderA inverted exclamation mark-D-glucoside

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4855	48.55%
Caco-2	-	0.8942	89.42%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	-	0.5540	55.40%
OATP1B1 inhibitior	+	0.9492	94.92%
OATP1B3 inhibitior	+	0.9740	97.40%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5190	51.90%
P-glycoprotein inhibitior	-	0.6836	68.36%
P-glycoprotein substrate	-	0.7649	76.49%
CYP3A4 substrate	+	0.6462	64.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8324	83.24%
CYP3A4 inhibition	-	0.9108	91.08%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9173	91.73%
CYP2D6 inhibition	-	0.9514	95.14%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.6591	65.91%
CYP inhibitory promiscuity	-	0.7292	72.92%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9162	91.62%
Skin irritation	-	0.8153	81.53%
Skin corrosion	-	0.9600	96.00%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5964	59.64%
Micronuclear	+	0.6633	66.33%
Hepatotoxicity	-	0.6823	68.23%
skin sensitisation	-	0.9373	93.73%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6613	66.13%
Acute Oral Toxicity (c)	III	0.6624	66.24%
Estrogen receptor binding	+	0.7761	77.61%
Androgen receptor binding	+	0.6838	68.38%
Thyroid receptor binding	+	0.5270	52.70%
Glucocorticoid receptor binding	+	0.6437	64.37%
Aromatase binding	+	0.5607	56.07%
PPAR gamma	+	0.7042	70.42%
Honey bee toxicity	-	0.7631	76.31%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6349	63.49%
Fish aquatic toxicity	+	0.7079	70.79%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5880	P60568	Interleukin-2	35.6 nM	Kd	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.62%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.70%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.53%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.35%	96.09%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	93.15%	86.92%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.99%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.98%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.56%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.33%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.17%	96.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	90.29%	96.21%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	88.75%	95.78%
CHEMBL1907	P15144	Aminopeptidase N	88.41%	93.31%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.02%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.88%	95.89%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	86.53%	95.53%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.52%	85.14%
CHEMBL1951	P21397	Monoamine oxidase A	84.68%	91.49%
CHEMBL4302	P08183	P-glycoprotein 1	83.19%	92.98%
CHEMBL3438	Q05513	Protein kinase C zeta	82.67%	88.48%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.25%	92.62%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	81.93%	80.78%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.76%	92.38%

Plants that contains it

• Amorpha fruticosa
• Astragalus mongholicus
• Astragalus trimestris
• Balanophora involucrata
• Dracaena cochinchinensis
• Glycyrrhiza glabra
• Glycyrrhiza pallidiflora
• Maackia amurensis
• Phyllolobium chinense
• Styphnolobium japonicum
• Trifolium pratense

Cross-Links

• PubChem: 5318267
• NPASS: NPC229729
• LOTUS: LTS0240351
• wikiData: Q27159206