Details of the Drug

General Information of Drug (ID: DMEHRAJ)

Drug Name
Rutin
Synonyms
RUTIN; 153-18-4; rutoside; Phytomelin; Quercetin 3-rutinoside; Birutan; Eldrin; Rutin trihydrate; Myrticolorin; Venoruton; Bioflavonoid; Paliuroside; Tanrutin; Osyritrin; Rutine; Rutozyd; 3-Rutinosyl quercetin; 3-Rhamnoglucosylquercetin; Quercetin 3-O-rutinoside; Rutosido; Rutosidum; Rutinum; Globularicitrin; Quercetin-3-rutinoside; Rutabion; Violaquercitrin; Globulariacitrin; Melin; Rutinic acid; Birutan Forte; Birutin; Quercetin rhamnoglucosine; Quercetin-3beta-rutinoside; UNII-5G06TVY3R7; Oxyritin; Rutosid; Ilixanthin; Rutinion acid
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): 3 Molecular Weight (mw) 610.5
Logarithm of the Partition Coefficient (xlogp) -1.3
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 10
Hydrogen Bond Acceptor Count (hbondacc) 16
Chemical Identifiers
Formula
C27H30O16
IUPAC Name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(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]oxychromen-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=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
InChI
InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
InChIKey
IKGXIBQEEMLURG-NVPNHPEKSA-N
Cross-matching ID
PubChem CID
5280805
ChEBI ID
CHEBI:28527
CAS Number
153-18-4
DrugBank ID
DB01698
TTD ID
D09ALJ
VARIDT ID
DR01181
INTEDE ID
DR2149

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Dihydrodiol dehydrogenase type I (AKR1C3) TT5ZWB6 AK1C3_HUMAN Inhibitor [1]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Alpha-L-rhamnosidase (lrA) DEC389G A0A385NJR4_9BACI Substrate [2]
Alpha-L-rhamnosidase (lrA) DEBI82Z A0A1V8Q7P3_9BIF Substrate [3]
Alpha-L-rhamnosidase (lrA) DE7BILX A0A1H8EBM0_9BACE Substrate [2]
Alpha-L-rhamnosidase (lrA) DE13AYF A0A179YH30_LACRH Substrate [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
60 kDa heat shock protein, mitochondrial (HSPD1) OTTO1Y11 CH60_HUMAN Gene/Protein Processing [4]
Acetylcholinesterase (ACHE) OT2H8HG6 ACES_HUMAN Gene/Protein Processing [5]
Activated CDC42 kinase 1 (TNK2) OTRGG0T8 ACK1_HUMAN Gene/Protein Processing [4]
Aldehyde dehydrogenase, mitochondrial (ALDH2) OTKJ9I3N ALDH2_HUMAN Gene/Protein Processing [5]
Amine oxidase A (MAOA) OT8NIWMQ AOFA_HUMAN Gene/Protein Processing [5]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [6]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [7]
Arginase-1 (ARG1) OTHZITAM ARGI1_HUMAN Gene/Protein Processing [5]
Aromatase (CYP19A1) OTZ6XF74 CP19A_HUMAN Gene/Protein Processing [8]
Aryl hydrocarbon receptor (AHR) OTFE4EYE AHR_HUMAN Protein Interaction/Cellular Processes [9]
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
Dihydrodiol dehydrogenase type I (AKR1C3) DTT AKR1C3 4.06E-01 1.39 0.74
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
2 Identification of rutin deglycosylated metabolites produced by human intestinal bacteria using UPLC-Q-TOF/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jun 1;898:95-100.
3 Metabolism of rutin and poncirin by human intestinal microbiota and cloning of their metabolizing alpha-L-rhamnosidase from Bifidobacterium dentium. J Microbiol Biotechnol. 2015 Jan;25(1):18-25.
4 Epicatechin and a cocoa polyphenolic extract modulate gene expression in human Caco-2 cells. J Nutr. 2004 Oct;134(10):2509-16.
5 Combination of metabolomics and network pharmacology analysis to decipher the mechanisms of total flavonoids of Litchi seed against prostate cancer. J Pharm Pharmacol. 2023 Jul 5;75(7):951-968. doi: 10.1093/jpp/rgad035.
6 Herbacetin induces apoptosis in HepG2 cells: Involvements of ROS and PI3K/Akt pathway. Food Chem Toxicol. 2013 Jan;51:426-33. doi: 10.1016/j.fct.2012.09.036. Epub 2012 Oct 12.
7 Chemical composition of total flavonoids from Salvia chinensia Benth and their pro-apoptotic effect on hepatocellular carcinoma cells: potential roles of suppressing cellular NF-B signaling. Food Chem Toxicol. 2013 Dec;62:420-6. doi: 10.1016/j.fct.2013.09.008. Epub 2013 Sep 12.
8 Induction and inhibition of aromatase (CYP19) activity by natural and synthetic flavonoid compounds in H295R human adrenocortical carcinoma cells. Toxicol Sci. 2004 Nov;82(1):70-9.
9 Plant polyphenols differentially modulate inflammatory responses of human keratinocytes by interfering with activation of transcription factors NFB and AhR and EGFR-ERK pathway. Toxicol Appl Pharmacol. 2011 Sep 1;255(2):138-49.