Details of the Drug

General Information of Drug (ID: DMNARGO)

Drug Name
Phlorizin
Synonyms
Phlorizin; Phloridzin; 60-81-1; Phlorhizin; Phlorizoside; Floridzin; Phlorrhizin; Phloretin 2'-glucoside; Phlorrhizen; Phloridzosid; Phlorizine; UNII-CU9S17279X; Phloretin-2'-O-beta-glucoside; AI3-19835; NSC 2833; Phloridzin dihydrate; EINECS 200-487-1; Phloretin-2'-beta-glucoside; CHEBI:8113; CHEMBL245067; IOUVKUPGCMBWBT-QNDFHXLGSA-N; CU9S17279X; 2'-(beta-D-Glucopyranosyloxy)-4',6'-dihydroxy-3-(4-hydroxyphenyl)propiophenone; 1-[2-(beta-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)-1-propanone; 1-Propanone, 1-(2-(b
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 436.4
Logarithm of the Partition Coefficient (xlogp) 1.2
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 7
Hydrogen Bond Acceptor Count (hbondacc) 10
Chemical Identifiers
Formula
C21H24O10
IUPAC Name
1-[2,4-dihydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-3-(4-hydroxyphenyl)propan-1-one
Canonical SMILES
C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)O
InChI
InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-15-8-12(24)7-14(26)17(15)13(25)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-24,26-29H,3,6,9H2/t16-,18-,19+,20-,21-/m1/s1
InChIKey
IOUVKUPGCMBWBT-QNDFHXLGSA-N
Cross-matching ID
PubChem CID
6072
ChEBI ID
CHEBI:8113
CAS Number
60-81-1
TTD ID
D06WAL
VARIDT ID
DR00950
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Sodium/glucose cotransporter 1 (SGLT1) TT2UE56 SC5A1_HUMAN Inhibitor [2]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 2 (ABCC2) DTFI42L MRP2_HUMAN Substrate [3]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Nitric oxide synthase 3 (NOS3) OTLDT7NR NOS3_HUMAN Gene/Protein Processing [4]
Sodium/glucose cotransporter 1 (SLC5A1) OT0T78JI SC5A1_HUMAN Drug Response [5]
Sodium/glucose cotransporter 2 (SLC5A2) OT93UUDI SC5A2_HUMAN Gene/Protein Processing [6]
UDP-glucuronosyltransferase 1A1 OTH1C8OJ UD11_HUMAN Gene/Protein Processing [7]
UDP-glucuronosyltransferase 1A10 OTOTZVEY UD110_HUMAN Gene/Protein Processing [7]
UDP-glucuronosyltransferase 1A3 OTUEOER3 UD13_HUMAN Gene/Protein Processing [7]
UDP-glucuronosyltransferase 1A7 OTY4JJ32 UD17_HUMAN Gene/Protein Processing [7]
UDP-glucuronosyltransferase 1A8 OTTMABBG UD18_HUMAN Gene/Protein Processing [7]
UDP-glucuronosyltransferase 1A9 OTPCHAFX UD19_HUMAN Gene/Protein Processing [7]
UDP-glucuronosyltransferase 2B15 OTABTFU2 UDB15_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Discovery agent
ICD Disease Classification N.A.
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Sodium/glucose cotransporter 1 (SGLT1) DTT SLC5A1 9.67E-01 0.08 0.42
Multidrug resistance-associated protein 2 (ABCC2) DTP MRP2 7.65E-01 -2.63E-02 -1.32E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4757).
2 J Biol Chem. 1988 Jan 5;263(1):187-92.High affinity phlorizin binding to the LLC-PK1 cells exhibits a sodium:phlorizin stoichiometry of 2:1.
3 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
4 Physiological concentrations of dietary polyphenols regulate vascular endothelial cell expression of genes important in cardiovascular health. Br J Nutr. 2010 May;103(10):1398-403.
5 D-Glucose-recognition and phlorizin-binding sites in human sodium/D-glucose cotransporter 1 (hSGLT1): a tryptophan scanning study. Biochemistry. 2007 Nov 27;46(47):13616-28. doi: 10.1021/bi701193x. Epub 2007 Nov 6.
6 Discovery of novel N--D-xylosylindole derivatives as sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the management of hyperglycemia in diabetes. J Med Chem. 2011 Jan 13;54(1):166-78. doi: 10.1021/jm101072y. Epub 2010 Dec 3.
7 Phloretin exhibits potential food-drug interactions by inhibiting human UDP-glucuronosyltransferases in vitro. Toxicol In Vitro. 2022 Oct;84:105447. doi: 10.1016/j.tiv.2022.105447. Epub 2022 Jul 19.