Details of the Drug

General Information of Drug (ID: DMS6IJ0)

Drug Name
RHEIN
Synonyms
Rhein; 478-43-3; Monorhein; Rheic acid; Rhubarb Yellow; Cassic acid; 4,5-Dihydroxyanthraquinone-2-carboxylic acid; Chrysazin-3-carboxylic acid; 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid; NSC 38629; Rheinic acid; 1,8-Dihydroxyanthraquinone-3-carboxylic acid; dipropionyl rhein; 1,8-Dihydroxy-3-carboxyanthraquinone; UNII-YM64C2P6UX; Rhein(Monorhein); 2-Anthracenecarboxylic acid, 9,10-dihydro-4,5-dihydroxy-9,10-dioxo-; CCRIS 5129; 9,10-Dihydro-4,5-dihydroxy-9,10-dioxo-2-anthracenecarboxylic acid; C15H8O6
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Affected Organisms
Staphylococcus aureusHelicobacter pylori
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 284.22
Logarithm of the Partition Coefficient (xlogp) 2.2
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1.6-2.6 h [2]
Clearance
The renal clearance of drug is 0.1 L/h [2]
Elimination
37% of drug is excreted in urine and 53% of drug in feces as estimated in rats [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 4 - 10 hours [2]
Vd
The volume of distribution (Vd) of drug is 15-60 L [2]
Chemical Identifiers
Formula
C15H8O6
IUPAC Name
4,5-dihydroxy-9,10-dioxoanthracene-2-carboxylic acid
Canonical SMILES
C1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)C(=O)O
InChI
InChI=1S/C15H8O6/c16-9-3-1-2-7-11(9)14(19)12-8(13(7)18)4-6(15(20)21)5-10(12)17/h1-5,16-17H,(H,20,21)
InChIKey
FCDLCPWAQCPTKC-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
10168
ChEBI ID
CHEMBL8825
CAS Number
478-43-3
UNII
YM64C2P6UX
DrugBank ID
DB13174
TTD ID
D0M2TY
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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
Heat shock protein 90 alpha (HSP90A) TT78R5H HS90A_HUMAN Inhibitor [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [4]
DNA oxidative demethylase ALKBH2 (ALKBH2) OTSQW0BG ALKB2_HUMAN Gene/Protein Processing [5]
Nuclear factor NF-kappa-B p105 subunit (NFKB1) OTNRRD8I NFKB1_HUMAN Gene/Protein Processing [6]
Receptor tyrosine-protein kinase erbB-2 (ERBB2) OTOAUNCK ERBB2_HUMAN Gene/Protein Processing [6]
TNF receptor-associated factor 1 (TRAF1) OTTLM5RU TRAF1_HUMAN Gene/Protein Processing [7]
Transcription factor p65 (RELA) OTUJP9CN TF65_HUMAN Gene/Protein Processing [6]
Tumor necrosis factor receptor type 1-associated DEATH domain protein (TRADD) OTBOSJHO TRADD_HUMAN Gene/Protein Processing [7]
Vascular endothelial growth factor A, long form OTIM9MZ3 VEGFA_HUMAN Gene/Protein Processing [6]
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
Heat shock protein 90 alpha (HSP90A) DTT HSP90AA1 3.96E-01 0.18 0.48
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 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.
2 Clinical pharmacokinetics of diacerein. Clin Pharmacokinet. 1998 Nov;35(5):347-59.
3 De Witte P, Lemli J: Excretion and distribution of [14C]rhein and [14C]rhein anthrone in rat. J Pharm Pharmacol. 1988 Sep;40(9):652-5.
4 Anthraquinones inhibit cytochromes P450 enzyme activity in silico and in vitro. J Appl Toxicol. 2021 Sep;41(9):1438-1445. doi: 10.1002/jat.4134. Epub 2021 Jan 12.
5 Hydrolyzable Tannins Are Iron Chelators That Inhibit DNA Repair Enzyme ALKBH2. Chem Res Toxicol. 2019 Jun 17;32(6):1082-1086. doi: 10.1021/acs.chemrestox.8b00398. Epub 2019 May 28.
6 Rhein inhibits angiogenesis and the viability of hormone-dependent and -independent cancer cells under normoxic or hypoxic conditions in vitro. Chem Biol Interact. 2011 Jul 15;192(3):220-32. doi: 10.1016/j.cbi.2011.03.013. Epub 2011 Mar 30.
7 Apoptotic effects of rhein through the mitochondrial pathways, two death receptor pathways, and reducing autophagy in human liver L02 cells. Environ Toxicol. 2019 Dec;34(12):1292-1302. doi: 10.1002/tox.22830. Epub 2019 Aug 21.