Pueraria glycoside

Details

• Internal ID: 643b0d5d-241d-4383-85de-c846b9cf18c2
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid C-glycosides
• IUPAC Name: 3-(3,4-dihydroxyphenyl)-7-hydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• SMILES (Canonical): C1=CC(=C(C=C1C2=COC3=C(C2=O)C=CC(=C3C4C(C(C(C(O4)CO)O)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C2=COC3=C(C2=O)C=CC(=C3[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)O
• InChI: InChI=1S/C21H20O10/c22-6-14-17(27)18(28)19(29)21(31-14)15-12(24)4-2-9-16(26)10(7-30-20(9)15)8-1-3-11(23)13(25)5-8/h1-5,7,14,17-19,21-25,27-29H,6H2/t14-,17-,18+,19-,21+/m1/s1
• InChI Key: GARZMRVWLORUSR-VPRICQMDSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₀
• Molecular Weight: 432.40 g/mol
• Exact Mass: 432.10564683 g/mol
• Topological Polar Surface Area (TPSA): 177.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): 0.09
• H-Bond Acceptor: 10
• H-Bond Donor: 7
• Rotatable Bonds: 3

Synonyms

• 117060-54-5
• Pueraria glycoside
• M7KVR1LSN0
• 3-(3,4-dihydroxyphenyl)-7-hydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• DTXSID20151700
• 3-(3,4-dihydroxyphenyl)-7-hydroxy-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)chromen-4-one
• RefChem:910473
• DTXCID9074191
• 3'-hydroxy Puerarin
• MFCD20133902
• 3-(3,4-dihydroxyphenyl)-7-hydroxy-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one
• 4H-1-Benzopyran-4-one, 3-(3,4-dihydroxyphenyl)-8-ss-D-glucopyranosyl-7-hydroxy-; 3-(3,4-Dihydroxyphenyl)-8-ss-D-glucopyranosyl-7-hydroxy-4H-1-benzopyran-4-one; 3'-Hydroxypuerarin; 8-C-Glucosyl-7,3',4'-trihydroxyisoflavone; NPI 031H; PG 1
• UNII-M7KVR1LSN0
• 3'-Hydroxypuerarin (Standard)
• orb1303762
• SCHEMBL2399617
• SCHEMBL29461995
• SCHEMBL29461996
• HY-N1980R
• GLXC-13714
• HMS6019E05
• HY-N1980
• MSK40255
• s3260
• ZB1874
• AKOS030573623
• 3-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-7-hydroxy-4H-benzopyran-4-one
• AC-34570
• DA-60264
• MS-27710
• PD087341
• CS-0018300
• (8-beta-d-glucopyranosyl-7-hydroxy-3-(3,4-dihydroxyphenyl)-4h-1-benzopyran-4-one)
• 3-(3,4-DIHYDROXYPHENYL)-8-.BETA.-D-GLUCOPYRANOSYL-7-HYDROXY-4H-1-BENZOPYRAN-4-ONE
• 4H-Benzopyran-4-one, 3-(3,4-dihydroxyphenyl)-8-beta-D-glucopyranosyl-7-hydroxy-
• 3-(3,4-dihydroxyphenyl)-7-hydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one
• 4H-1-BENZOPYRAN-4-ONE, 3-(3,4-DIHYDROXYPHENYL)-8-.BETA.-D-GLUCOPYRANOSYL-7-HYDROXY-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6665	66.65%
Caco-2	-	0.9407	94.07%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5728	57.28%
OATP2B1 inhibitior	+	0.5839	58.39%
OATP1B1 inhibitior	+	0.8938	89.38%
OATP1B3 inhibitior	+	0.9709	97.09%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.6894	68.94%
P-glycoprotein substrate	-	0.9093	90.93%
CYP3A4 substrate	+	0.5744	57.44%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8193	81.93%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9240	92.40%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.8355	83.55%
CYP2C8 inhibition	+	0.6069	60.69%
CYP inhibitory promiscuity	-	0.7806	78.06%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7252	72.52%
Eye corrosion	-	0.9936	99.36%
Eye irritation	-	0.7983	79.83%
Skin irritation	-	0.7691	76.91%
Skin corrosion	-	0.9606	96.06%
Ames mutagenesis	+	0.5935	59.35%
Human Ether-a-go-go-Related Gene inhibition	-	0.4869	48.69%
Micronuclear	+	0.6559	65.59%
Hepatotoxicity	+	0.6554	65.54%
skin sensitisation	-	0.8683	86.83%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.5790	57.90%
Acute Oral Toxicity (c)	IV	0.3746	37.46%
Estrogen receptor binding	+	0.5912	59.12%
Androgen receptor binding	+	0.7412	74.12%
Thyroid receptor binding	+	0.5608	56.08%
Glucocorticoid receptor binding	+	0.6244	62.44%
Aromatase binding	-	0.5556	55.56%
PPAR gamma	+	0.6522	65.22%
Honey bee toxicity	-	0.7958	79.58%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.6921	69.21%

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	99.60%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.36%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.84%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.15%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.26%	95.56%
CHEMBL4040	P28482	MAP kinase ERK2	86.71%	83.82%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.61%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.86%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.66%	86.92%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.49%	80.78%
CHEMBL3401	O75469	Pregnane X receptor	84.33%	94.73%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.44%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.36%	99.23%

Plants that contains it

• Pueraria montana var. lobata

Cross-Links

• PubChem: 5748205
• NPASS: NPC23137
• LOTUS: LTS0004022
• wikiData: Q72481523