Summary

Full nameuridine-5'-monophosphate
IUPAC name[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
Short namepU
MODOMICS code551U
Synonyms
2j4k
2qaf
2qcd
2qcn
[(2R,3S,4R,5R)-5-[2,4-bis(oxidanylidene)pyrimidin-1-yl]-3,4-bis(oxidanyl)oxolan-2-yl]methyl phosphate
[(2R,3S,4R,5R)-5-(2,4-dioxo-1-pyrimidinyl)-3,4-dihydroxy-2-oxolanyl]methyl phosphate
[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
2zz6
3387-36-8
3bar
3dxg
3ex3
58-97-9
5'-O-phosphonatouridine
5'-UMP
5'-UMP disodium
5'-uridylate
5'-uridylic acid (8CI)(9CI)
5'-URIDYLIC ACID, DISODIUM SALT
A832094
AC1LWL1G
C9-H11-N2-O9-P.2Na
C9H11N2O9P.2Na
C9H13N2O9P.2Na
CCRIS 6562
CHEBI:57865
CID1778309
cis-2,2-Dimethyl-3-hexene
Disodium 5'-UMP
Disodium 5'-uridylate
Disodium UMP
Disodium uridine 5'-monophosphate
Disodium uridine 5'-phosphate
Disodium uridine-5'-monophosphate
EINECS 222-211-9
NSC 20257
Q27125012
UMP
UMP dianion
UMP(2-)
UNII-KD8E20071T
Uridine, 5'-dihydrogen phosphate, disodium salt
Uridine 5'-monophosphate
uridine 5'-monophosphate(2-)
Uridine 5'MP, disodium salt
Uridine 5'-phosphate
Uridine monophosphate
Uridine monophosphate disodium
Uridine-5-monophosphate disodium salt
uridylate

Nature of the modified residueNatural
Residue unique ID255
Found in RNAYes
Related nucleosides60
RCSB ligands

U5P


Chemical information

Sum formulaC9H11N2O9P
Type of moietynucleotide
Degeneracynot aplicable
SMILESO=c1cc[n]([C@@H]2O[C@H](COP(=O)([O-])[O-])[C@@H](O)[C@H]2O)c(=O)[nH]1
logP-1.8585
TPSA186.78
Number of atoms21
Number of Hydrogen Bond Acceptors 1 (HBA1)7
Number of Hydrogen Bond Acceptors 2 (HBA2)10
Number of Hydrogen Bond Donors (HBD)3
InChIInChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/p-2/t4-,6-,7-,8-/m1/s1
InChIKeyDJJCXFVJDGTHFX-XVFCMESISA-L
Search the molecule in external databases ChEMBL  ChemAgora  ChEBI  PubChem Compound Database  Ligand Expo  ChemSpider  WIPO 
PubChem CID
PubChem SIDs

* Chemical properties calculated with Open Babel - O'Boyle et al. Open Babel: An open chemical toolbox. J Cheminform 3, 33 (2011) (link)


Download Structures

2D   .png .mol .mol2 .sdf .pdb .smi
3D   .mol .mol2 .sdf .pdb

Tautomers

Tautomers SMILES
O=c1ccn(C2OC(COP(=O)([O-])[O-])C(O)C2O)c(=O)[nH]1 tautomer #0
O=c1ccn(C2OC(COP(=O)([O-])[O-])C(O)C2O)c(O)n1 tautomer #1
Oc1ccn(C2OC(COP(=O)([O-])[O-])C(O)C2O)c(=O)n1 tautomer #2

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
pU pU pU

* CYP Metabolic sites predicted with SMARTCyp. SMARTCyp is a method for prediction of which sites in a molecule that are most liable to metabolism by Cytochrome P450. It has been shown to be applicable to metabolism by the isoforms 1A2, 2A6, 2B6, 2C8, 2C19, 2E1, and 3A4 (CYP3A4), and specific models for the isoform 2C9 (CYP2C9) and isoform 2D6 (CYP2D6). CYP3A4, CYP2D6, and CYP2C9 are the three of the most important enzymes in drug metabolism since they are involved in the metabolism of more than half of the drugs used today. The three top-ranked atoms are highlighted. See: SmartCYP and SmartCYP - background; Patrik Rydberg, David E. Gloriam, Lars Olsen, The SMARTCyp cytochrome P450 metabolism prediction server, Bioinformatics, Volume 26, Issue 23, 1 December 2010, Pages 2988–2989 (link)


LC-MS Information

Monoisotopic massNone
Average mass322.165
[M+H]+ not available
Product ions not available
Normalized LC elution time * not available
LC elution order/characteristics not available

* normalized to guanosine (G), measured with a RP C-18 column with acetonitrile/ammonium acetate as mobile phase.

Last modification of this entry: Sept. 29, 2021


Copyright © Genesilico - All rights reserved
If you have any advice or suggestions for corrections or improvements, please contact: Andrea Cappannini - lp.vog.bcmii@ininnappaca