Summary

Full namecytidine-5'-monophosphate
IUPAC name[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
Short namepC
MODOMICS code551C
Synonyms
[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1-pyrimidinyl)-3,4-dihydroxy-2-oxolanyl]methyl phosphate
[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
[(2R,3S,4R,5R)-5-(4-azanyl-2-oxidanylidene-pyrimidin-1-yl)-3,4-bis(oxidanyl)oxolan-2-yl]methyl phosphate
5'-CYTIDYLIC ACID
5'-O-phosphonatocytidine
63-37-6
84-52-6
A834351
AC1OEJZP
CHEBI:60377
CID7058165
CJ-10966
CMP
CMP dianion
CMP(2-)
Cytidine 5'-monophosphate
cytidine 5'-monophosphate(2-)
Cytidine 5'-phosphate
Cytidine-5'-monophosphate
Cytidine-5-monophosphate dianion
cytidine-monophosphate
cytidine-P
cytidine-phosphate
cytidylate
cytidylic acid
D0S2QZ
LS-190174
Q27104867
ZINC03861744

Nature of the modified residueNatural
Residue unique ID300
Found in RNAYes
Related nucleosides46
RCSB ligands

C5P


Chemical information

Sum formulaC9H12N3O8P
Type of moietynucleotide
Degeneracynot aplicable
SMILESNc1nc(=O)[n]([C@H]2[C@H](O)[C@H](O)[C@@H](COP(=O)([O-])[O-])O2)cc1
logP-0.9884
TPSA192.83
Number of atoms21
Number of Hydrogen Bond Acceptors 1 (HBA1)8
Number of Hydrogen Bond Acceptors 2 (HBA2)11
Number of Hydrogen Bond Donors (HBD)3
InChIInChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/p-2/t4-,6-,7-,8-/m1/s1
InChIKeyIERHLVCPSMICTF-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
N=c1[nH]c(=O)n(C2C(O)C(O)C(COP(=O)([O-])[O-])O2)cc1 tautomer #0
Nc1nc(=O)n(C2C(O)C(O)C(COP(=O)([O-])[O-])O2)cc1 tautomer #1
N=c1nc(O)n(C2C(O)C(O)C(COP(=O)([O-])[O-])O2)cc1 tautomer #2

Tautomer image Show Image

Predicted CYP Metabolic Sites

CYP3A4 CYP2D6 CYP2C9
pC pC pC

* 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 mass321.181
[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


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