General Information of Drug (ID: DMR5GSB)

Drug Name
Tetrahydrouridine
Synonyms
3,4,5,6-Tetrahydrouridine; NSC-112907; NSC 112907; CHEMBL2311128; 18771-50-1; U 23284; NSC-112907-D; BRN 0752319; 2(1H)-pyrimidinone, tetrahydro-4-hydroxy-1-beta-D-ribofuranosyl-; NSC112907; AC1L1H1G; SCHEMBL587704; 3,4,5, 6-Tetrahydrouridine; 2(1H)-Pyrimidinone, tetrahydro-4-hydroxy-1-.beta.-D-ribofuranosyl-; UCKYOOZPSJFJIZ-XVKVHKPRSA-N; MolPort-044-561-340; BDBM50421666; AKOS032953792; DB12484; LS-7719; CS-7633; HY-15345; 3,4,5,6-Tetrahydrouridine (> 80% by HPLC); J-012078
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Phase 2 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 248.23
Logarithm of the Partition Coefficient (xlogp) -2.4
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C9H16N2O6
IUPAC Name
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one
Canonical SMILES
C1CN(C(=O)NC1O)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
InChI
InChI=1S/C9H16N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h4-8,12-15H,1-3H2,(H,10,16)/t4-,5?,6-,7-,8-/m1/s1
InChIKey
UCKYOOZPSJFJIZ-XVKVHKPRSA-N
Cross-matching ID
PubChem CID
29243
CAS Number
18771-50-1
DrugBank ID
DB12484
TTD ID
D0I5OR
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Cytidine deaminase (CDA) TTQ12RK CDD_HUMAN Modulator [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Cytidine deaminase (CDA) OT3HXP6N CDD_HUMAN Gene/Protein Processing [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Quantitative determination of the cytidine deaminase inhibitor tetrahydrouridine (THU) in mouse plasma by liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun Mass Spectrom. 2007;21(13):1991-7.
2 Tetrahydrouridine inhibits cell proliferation through cell cycle regulation regardless of cytidine deaminase expression levels. PLoS One. 2012;7(5):e37424.
3 Comparison of in vitro metabolic conversion of capecitabine to 5-FU in rats, mice, monkeys and humans--toxicological implications. J Toxicol Sci. 2011 Aug;36(4):411-22.