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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2009-02-04 15:11:57 UTC
Update Date2020-02-26 21:35:39 UTC
HMDB IDHMDB0011691
Secondary Accession Numbers
  • HMDB11691
Metabolite Identification
Common NameCytidine 2',3'-cyclic phosphate
DescriptionCytidine 2',3'-cyclic phosphate is a cytidine nucleotide containing a pyrophosphate group esterified to C2 and C3(cyclic) of the sugar moiety. A cyclic nucleotide is any nucleotide in which the phosphate group is bonded to two of the sugar's hydroxyl groups, forming a cyclical or ring structure. 2',3' cyclic CMP is a substrate for 2',3'-cyclic-nucleotide 3'-phosphodiesterase (EC 3.1.4.37). This enzyme (also called CNP) catalyzes the chemical reaction: nucleoside 2',3'-cyclic phosphate + H2O <-> nucleoside 2'-phosphate. CNP is a myelin-associated enzyme that makes up 4% of total CNS myelin protein, and is thought to undergo significant age-associated changes. The absence of CNP causes axonal swelling and neuronal degeneration. The biological role of cyclic 2',3' monophosphates is not clear, although it is thought to have something to do with neuronal stasis or development.
Structure
Data?1582752939
Synonyms
ValueSource
Glutathione disulphideChEBI
GSSGChEBI
Oxidised glutathioneChEBI
Oxidized glutathioneChEBI
OXIDIZED glutathione disulfideChEBI
OxiglutationeChEBI
GlutathioneKegg
OXIDIZED glutathione disulphideGenerator
Glutathione disulfide, ion(1-)MeSH
Disulfide, glutathioneMeSH
Glutathione, oxidizedMeSH
2',3' Cyclic CMPHMDB
2',3' Cyclic-CMPHMDB
Cyclic(2',3')-CMPHMDB
Cytidine-2',3'-cyclophosphateHMDB
Cytidine 2',3'-cyclic phosphoric acidGenerator
Chemical FormulaC9H12N3O7P
Average Molecular Weight305.1812
Monoisotopic Molecular Weight305.041286265
IUPAC Name1-[(3aR,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-4-amino-1,2-dihydropyrimidin-2-one
Traditional Name1-[(3aR,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-4-aminopyrimidin-2-one
CAS Registry Number15718-51-1
SMILES
NC1=NC(=O)N(C=C1)C1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12
InChI Identifier
InChI=1S/C9H12N3O7P/c10-5-1-2-12(9(14)11-5)8-7-6(4(3-13)17-8)18-20(15,16)19-7/h1-2,4,6-8,13H,3H2,(H,15,16)(H2,10,11,14)/t4-,6-,7-,8?/m1/s1
InChI KeyNMPZCCZXCOMSDQ-ZRTZXPPTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentPeptides
Alternative Parents
Substituents
  • Alpha peptide
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Tetracarboxylic acid or derivatives
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Amino acid or derivatives
  • Amino acid
  • Dialkyldisulfide
  • Organic disulfide
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Primary aliphatic amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organopnictogen compound
  • Primary amine
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility20.5 g/LALOGPS
logP-1.8ALOGPS
logP-2.3ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)-0.65ChemAxon
pKa (Strongest Basic)1.76ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area143.91 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity61.64 m³·mol⁻¹ChemAxon
Polarizability25.76 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00rx-5940000000-8ab4c4a156dd13eee927Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-3913000000-33e0f0bba64d9939e84eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0901000000-e7f102f4bea63f5e5fdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2900000000-cb3d80cc5dffe05f6888Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9600000000-6f0a550e121f5621a2f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0nmi-1394000000-318f2cd988d67fcae4caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-7971000000-a038ae20ec94c0e427e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-a171fcfbd0db4fdcd822Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03310
Phenol Explorer Compound IDNot Available
FooDB IDFDB023147
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC00127
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGlutathione disulfide
METLIN IDNot Available
PubChem Compound65359
PDB IDNot Available
ChEBI ID17858
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

General function:
Involved in 2',3'-cyclic-nucleotide 3'-phosphodiesterase activity
Specific function:
May participate in RNA metabolism in the myelinating cell, CNP is the third most abundant protein in central nervous system myelin (By similarity).
Gene Name:
CNP
Uniprot ID:
P09543
Molecular weight:
47578.22