Details of the Drug

General Information of Drug (ID: DMYA50U)

Drug Name
phloretin
Synonyms
phloretin; 60-82-2; 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one; Dihydronaringenin; Phloretol; 3-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-1-propanone; NSC 407292; UNII-S5J5OE47MK; 1-Propanone, 3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)-; CCRIS 7459; beta-(p-Hydroxyphenyl)phloropropiophenone; 2',4',6'-Trihydroxy-3-(p-hydroxyphenyl)propiophenone; 2',4',6'-Trihydroxy-3-(4-Hydroxyphenyl)propiophenone; EINECS 200-488-7; NSC407292; S5J5OE47MK; beta-(p-Hydroxyphenyl)-2,4,6-trihydroxypropiophenone
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 274.27
Logarithm of the Partition Coefficient (xlogp) 2.6
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 4
Hydrogen Bond Acceptor Count (hbondacc) 5
Chemical Identifiers
Formula
C15H14O5
IUPAC Name
3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one
Canonical SMILES
C1=CC(=CC=C1CCC(=O)C2=C(C=C(C=C2O)O)O)O
InChI
InChI=1S/C15H14O5/c16-10-4-1-9(2-5-10)3-6-12(18)15-13(19)7-11(17)8-14(15)20/h1-2,4-5,7-8,16-17,19-20H,3,6H2
InChIKey
VGEREEWJJVICBM-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
4788
ChEBI ID
CHEBI:17276
CAS Number
60-82-2
DrugBank ID
DB07810
TTD ID
D0HD2G
VARIDT ID
DR00911
INTEDE ID
DR1943

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Aquaporin-9 (AQP9) TTQEI32 AQP9_HUMAN Inhibitor [2]
Chloride channel protein 3 (CLC-3) TT8XNZ7 CLCN3_HUMAN Blocker (channel blocker) [3]
Solute carrier family 23 member 1 (SLC23A1) TT6XAGK S23A1_HUMAN Inhibitor [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [5]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DE85D2P UD19_HUMAN Substrate [5]
UDP-glucuronosyltransferase 1A8 (UGT1A8) DE2GB8N UD18_HUMAN Substrate [5]
UDP-glucuronosyltransferase 1A7 (UGT1A7) DEZO4N3 UD17_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Estrogen receptor beta (ESR2) OTXNR2WQ ESR2_HUMAN Protein Interaction/Cellular Processes [6]
Glycogen synthase kinase-3 beta (GSK3B) OTL3L14B GSK3B_HUMAN Gene/Protein Processing [7]
Nitric oxide synthase 3 (NOS3) OTLDT7NR NOS3_HUMAN Gene/Protein Processing [8]
Sex hormone-binding globulin (SHBG) OTPWU5IW SHBG_HUMAN Protein Interaction/Cellular Processes [9]
Sodium/hydrogen exchanger 1 (SLC9A1) OT6HNHFV SL9A1_HUMAN Gene/Protein Processing [10]
Sodium/hydrogen exchanger 9B2 (SLC9B2) OTZVOY8T SL9B2_HUMAN Gene/Protein Processing [11]
Solute carrier family 2, facilitated glucose transporter member 1 (SLC2A1) OTA675TJ GTR1_HUMAN Gene/Protein Processing [12]
Solute carrier family 2, facilitated glucose transporter member 2 (SLC2A2) OTBL2W7R GTR2_HUMAN Gene/Protein Processing [13]
UDP-glucuronosyltransferase 1-6 OTGTQ2C9 UD16_HUMAN Gene/Protein Processing [14]
UDP-glucuronosyltransferase 1A1 OTH1C8OJ UD11_HUMAN Gene/Protein Processing [14]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction 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: 4285).
2 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. (Target id: 696).
3 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. (Target id: 702).
4 A family of mammalian Na+-dependent L-ascorbic acid transporters. Nature. 1999 May 6;399(6731):70-5.
5 Differential and special properties of the major human UGT1-encoded gastrointestinal UDP-glucuronosyltransferases enhance potential to control chemical uptake. J Biol Chem. 2004 Jan 9;279(2):1429-41.
6 Relationship between estrogen receptor-binding and estrogenic activities of environmental estrogens and suppression by flavonoids. Biosci Biotechnol Biochem. 2002 Jul;66(7):1479-87. doi: 10.1271/bbb.66.1479.
7 Modulation of key elements of the Wnt pathway by apple polyphenols. J Agric Food Chem. 2006 Sep 20;54(19):7041-6. doi: 10.1021/jf0606611.
8 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.
9 Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and -fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27.
10 Alternative splicing of NHE-1 mediates Na-Li countertransport and associates with activity rate. Diabetes. 2003 Jun;52(6):1511-8. doi: 10.2337/diabetes.52.6.1511.
11 A human Na+/H+ antiporter sharing evolutionary origins with bacterial NhaA may be a candidate gene for essential hypertension. Proc Natl Acad Sci U S A. 2007 Nov 20;104(47):18677-81. doi: 10.1073/pnas.0707120104. Epub 2007 Nov 13.
12 The inhibitory effects of flavonoids and antiestrogens on the Glut1 glucose transporter in human erythrocytes. Chem Biol Interact. 2003 Dec 15;146(3):225-35. doi: 10.1016/j.cbi.2003.06.001.
13 Involvement of pregnane X receptor in the impaired glucose utilization induced by atorvastatin in hepatocytes. Biochem Pharmacol. 2016 Jan 15;100:98-111.
14 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.