Details of the Drug

General Information of Drug (ID: DMI5DW1)

Drug Name
Hesperidin
Synonyms
hesperidin; 520-26-3; Cirantin; Hesperidoside; Hesper bitabs; Hesperetin-rutinosid; Hesperidine; UNII-E750O06Y6O; CCRIS 3940; (S)-(-)-Hesperidin; EINECS 208-288-1; NSC 44184; BRN 0075140; Hesperidin, (2S)-; Hesperetin 7-rutinoside; MLS001304066; (2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one; CHEBI:28775; USAF CF-3; Hesperidin, (S)-(-)-; Hesperitin-7-rhamnoglucoside; E750O06Y6O; C28H34O15; HESPERIDINE
Indication
Disease Entry ICD 11 Status REF
Vascular purpura 3B60 Approved [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 610.6
Logarithm of the Partition Coefficient (xlogp) -1.1
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 8
Hydrogen Bond Acceptor Count (hbondacc) 15
Chemical Identifiers
Formula
C28H34O15
IUPAC Name
(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Canonical SMILES
C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC(=C(C=C5)OC)O)O)O)O)O)O)O)O
InChI
InChI=1S/C28H34O15/c1-10-21(32)23(34)25(36)27(40-10)39-9-19-22(33)24(35)26(37)28(43-19)41-12-6-14(30)20-15(31)8-17(42-18(20)7-12)11-3-4-16(38-2)13(29)5-11/h3-7,10,17,19,21-30,32-37H,8-9H2,1-2H3/t10-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
InChIKey
QUQPHWDTPGMPEX-QJBIFVCTSA-N
Cross-matching ID
PubChem CID
10621
ChEBI ID
CHEMBL449317
CAS Number
520-26-3
UNII
E750O06Y6O
DrugBank ID
DB04703
TTD ID
D0I9HF
VARIDT ID
DR00632
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Voltage-gated calcium channel alpha Cav2.2 (CACNA1B) TT4FDG6 CAC1B_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cyclin-dependent kinase inhibitor 1 (CDKN1A) OTQWHCZE CDN1A_HUMAN Gene/Protein Processing [3]
Cyclin-dependent kinase inhibitor 1B (CDKN1B) OTNY5LLZ CDN1B_HUMAN Gene/Protein Processing [3]
Dual specificity mitogen-activated protein kinase kinase 5 (MAP2K5) OT6T408U MP2K5_HUMAN Post-Translational Modifications [3]
Tumor necrosis factor receptor superfamily member 25 (TNFRSF25) OTVZ7I3A TNR25_HUMAN Gene/Protein Processing [4]
Tumor necrosis factor receptor type 1-associated DEATH domain protein (TRADD) OTBOSJHO TRADD_HUMAN Gene/Protein Processing [4]
Vascular cell adhesion protein 1 OTP74K37 VCAM1_HUMAN Gene/Protein Processing [5]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Vascular purpura
ICD Disease Classification 3B60
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Voltage-gated calcium channel alpha Cav2.2 (CACNA1B) DTT CACNA1B 9.07E-01 7.11E-03 0.06
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2 In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Bioorg Med Chem Lett. 2010 Dec 15;20(24):7331-6.
3 Hesperidin delays cell cycle progression into the G0/G1 phase via suspension of MAPK signaling pathway in intrahepatic cholangiocarcinoma. J Biochem Mol Toxicol. 2022 Apr;36(4):e22981. doi: 10.1002/jbt.22981. Epub 2022 Jan 4.
4 Mangiferin has an additive effect on the apoptotic properties of hesperidin in Cyclopia sp. tea extracts. PLoS One. 2014 Mar 14;9(3):e92128. doi: 10.1371/journal.pone.0092128. eCollection 2014.
5 The effect of hesperidin supplementation on inflammatory markers in human adults: A systematic review and meta-analysis of randomized controlled clinical trials. Chem Biol Interact. 2019 Jul 1;307:8-15. doi: 10.1016/j.cbi.2019.04.016. Epub 2019 Apr 13.