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]
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
CHEBI:8825
CAS Number
478-43-3
DrugBank ID
DB13174
TTD ID
D0M2TY

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
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [4]
Beclin-1 (BECN1) OT4X293M BECN1_HUMAN Gene/Protein Processing [4]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [4]
Caspase-8 (CASP8) OTA8TVI8 CASP8_HUMAN Protein Interaction/Cellular Processes [4]
Caspase-9 (CASP9) OTD4RFFG CASP9_HUMAN Gene/Protein Processing [4]
Cytochrome P450 1A1 (CYP1A1) OTE4EFH8 CP1A1_HUMAN Gene/Protein Processing [5]
Cytochrome P450 1A2 (CYP1A2) OTLLBX48 CP1A2_HUMAN Gene/Protein Processing [5]
Cytochrome P450 2C19 (CYP2C19) OTFMJYYE CP2CJ_HUMAN Gene/Protein Processing [6]
Cytochrome P450 2C9 (CYP2C9) OTGLBN29 CP2C9_HUMAN Gene/Protein Processing [5]
Cytochrome P450 2D6 (CYP2D6) OTZJC802 CP2D6_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 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.
5 The natural anthraquinones from Rheum palmatum induced the metabolic disorder of melatonin by inhibiting human CYP and SULT enzymes. Toxicol Lett. 2016 Nov 16;262:27-38.
6 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.