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63-37-6 molecular structure
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{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

ChemBase ID: 70591
Molecular Formular: C9H14N3O8P
Molecular Mass: 323.196521
Monoisotopic Mass: 323.05185105
SMILES and InChIs

SMILES:
P(=O)(O)(O)OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1c(=O)nc(cc1)N
Canonical SMILES:
O[C@@H]1[C@H](O)[C@H](O[C@H]1n1ccc(nc1=O)N)COP(=O)(O)O
InChI:
InChI=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)/t4-,6-,7-,8-/m1/s1
InChIKey:
IERHLVCPSMICTF-XVFCMESISA-N

Cite this record

CBID:70591 http://www.chembase.cn/molecule-70591.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
IUPAC Traditional name
cytidine monophosphate
Synonyms
Cytidine 5'-Phosphate
Cytidine 5'-Phosphoric Acid
Cytidine Monophosphate
Cytidine Mono(dihydrogen phosphate)(Ester)
Cytidylic Acid
Cytosine 5'-Monophosphate
Cytidine 5'-Monophosphate
5'-Cytidylic acid
((2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
5'-Cytidylic acid
Cytidine monophosphate
5′-CMP
5′-Cytidylic acid
C-5′-P
Cytidine 5′-monophosphate
CAS Number
63-37-6
EC Number
200-556-6
MDL Number
MFCD00006544
Beilstein Number
46982
PubChem SID
162036306
24892358
PubChem CID
6131
CHEBI ID
17361
CHEMBL
307679
Chemspider ID
5901
Wikipedia Title
Cytidine_monophosphate

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 1.247557  H Acceptors
H Donor LogD (pH = 5.5) -5.362577 
LogD (pH = 7.4) -6.4509172  Log P -3.1532001 
Molar Refractivity 65.4177 cm3 Polarizability 26.073345 Å3
Polar Surface Area 175.14 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Water expand Show data source
Apperance
crystalline expand Show data source
White Solid expand Show data source
Melting Point
~222 °C (dec.) expand Show data source
205-208°C expand Show data source
Optical Rotation
[α]20/D +9±0.5°, c = 1% in 0.5 M Na2HPO4 expand Show data source
pKa
0.8, 4.5, 6.3 expand Show data source
Storage Condition
Refrigerator expand Show data source
Storage Warning
IRRITANT expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
false expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥98.0% (HPLC) expand Show data source
≥99% (HPLC) expand Show data source
95+% expand Show data source
Grade
Sigma Grade expand Show data source
Certificate of Analysis
Download expand Show data source
Impurities
~3% water expand Show data source
Biological Source
from yeast expand Show data source
Empirical Formula (Hill Notation)
C9H14N3O8P expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - C1131 external link
Application
Cytidine 5′-monophosphate (CMP) is used as a substrate of uridine monophosphate (UMP)/cytidine monophosphate (CMP) kinase (EC 2.7.4.4) to form CDP which upon phosphorylation to CTP supports DNA and RNA biosynthesis.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C1131.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - C998305 external link
A constituent of nucleic acids. It was isolated from yeast nucleic acid.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Parrou, J., et al.: Anal. Biochem., 248, 186 (1997)
  • • Phipps, A., et al.: Xenobiotica, 28, 527 (1997)
  • • Mohler, R., et al.: Anal. Chem., 78, 2700 (1997)
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PATENTS

PATENTS

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INTERNET

INTERNET

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