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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2009-01-29 15:28:58 UTC
Update Date2022-09-22 17:43:58 UTC
HMDB IDHMDB0011616
Secondary Accession Numbers
  • HMDB11616
Metabolite Identification
Common NameAdenosine 2',3'-cyclic phosphate
DescriptionAdenosine 2',3'-cyclic phosphate, also known as 2',3'-cyclic AMP or adenosine cyclic-2',3'-monophosphate, belongs to the class of organic compounds known as 2',3'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C2 and C3 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group. Adenosine 2',3'-cyclic phosphate has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make adenosine 2',3'-cyclic phosphate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Adenosine 2',3'-cyclic phosphate.
Structure
Thumb
Synonyms
ValueSource
Adenosine 2',3'-cyclic phosphoric acidGenerator
2',3'-Cyclic AMPMeSH
Adenosine cyclic-2',3'-monophosphateMeSH
2',3'-Cyclic AMP, monosodium saltMeSH
2',3'-Cyclic AMP, sodium saltMeSH
Adenosine cyclic 2,3 monophosphateMeSH
Adenosine cyclic 2',3'-monophosphateMeSH
2',3'-CAMPHMDB
2',3'-Cyclic adenosine monophosphateHMDB
Cyclic 2',3'-(hydrogen phosphate)-adenosineHMDB
Cyclic 2',3'-AMPHMDB
Chemical FormulaC10H12N5O6P
Average Molecular Weight329.2059
Monoisotopic Molecular Weight329.052519653
IUPAC Name4-(6-amino-9H-purin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-one
Traditional Name4-(6-aminopurin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-2-one
CAS Registry Number634-01-5
SMILES
NC1=NC=NC2=C1N=CN2C1OC(CO)C2OP(O)(=O)OC12
InChI Identifier
InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7-6(4(1-16)19-10)20-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)
InChI KeyKMYWVDDIPVNLME-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2',3'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C2 and C3 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassCyclic purine nucleotides
Direct Parent2',3'-cyclic purine nucleotides
Alternative Parents
Substituents
  • 2',3'-cyclic purine ribonucleotide
  • Ribonucleoside 3'-phosphate
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monosaccharide
  • Imidolactam
  • Pyrimidine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Azole
  • 1,3_dioxaphospholane
  • Heteroaromatic compound
  • Imidazole
  • Tetrahydrofuran
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Primary amine
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Primary alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.026 +/- 0.00096 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028321
KNApSAcK IDC00001132
Chemspider ID390207
KEGG Compound IDC08355
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSedoheptulose
METLIN IDNot Available
PubChem Compound2024
PDB IDNot Available
ChEBI ID175195
Food Biomarker OntologyNot Available
VMH IDM03165
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Krall JF, Swensen JL, Korenman SG: Hormonal control of uterine contraction. Characterization od cyclic AMP-dependent membrane properties in the myometrium. Biochim Biophys Acta. 1976 Nov 2;448(4):578-88. [PubMed:184841 ]
  2. Schoffstall AM: Prebiotic phosphorylation of nucleosides in formamide. Orig Life. 1976 Dec;7(4):399-412. [PubMed:1023139 ]
  3. Cheng C, Fan C, Wan R, Tong C, Miao Z, Chen J, Zhao Y: Phosphorylation of adenosine with trimetaphosphate under simulated prebiotic conditions. Orig Life Evol Biosph. 2002 Jun;32(3):219-24. [PubMed:12227426 ]
  4. Ghandour MS, Derer P, Labourdette G, Delaunoy JP, Langley OK: Glial cell markers in the reeler mutant mouse: a biochemical and immunohistological study. J Neurochem. 1981 Jan;36(1):195-200. [PubMed:6257845 ]
  5. Wells MR, Sprinkle TJ: Purification of rat 2',3'-cyclic nucleotide 3'-phosphodiesterase. J Neurochem. 1981 Feb;36(2):633-9. [PubMed:6257858 ]
  6. Reddy NB, Askanas V, Engel WK: Demonstration of 2',3'-cyclic nucleotide 3'-phosphohydrolase in cultured human Schwann cells. J Neurochem. 1982 Sep;39(3):887-9. [PubMed:6284879 ]
  7. 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