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Human Metabolome Database Version 2.5

 

Showing metabocard for Guanosine 2',3'-cyclic phosphate (HMDB11629)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2009-01-30 10:21:23
Update Date 2009-05-05 21:07:37
Accession Number HMDB11629
Secondary Accession Numbers Not Available
Common Name Guanosine 2',3'-cyclic phosphate
Description 2',3'-Cyclic GMP is a cyclic guanosine derivative that is a precursor to 3'-GMP. The enzyme 2'3'-cyclic-nucleotide 2'-phosphodiesterase (E.C. 3.1.4.16) catalyses the hydrolysis of both 2',3'-cyclic AMP and 2',3'-cyclic GMP into 3'-AMP and 3'-GMP, respectively, at the 3'-terminal of RNA. 2',3'-cyclic phosphate termini are produced, as either intermediates or final products, during RNA cleavage by many different endoribonucleases. The enzyme RNA 3'-phosphate cyclase also converts the 3'-terminal phosphate in RNA into the 2',3'-cyclic phosphodiester in the ATP-dependent reaction which involves formation of the covalent cyclase-AMP and the RNA-N3' pp5' A intermediates (PMID: 10397337). This enzyme could be involved in the maintenance of cyclic ends in tRNA splicing intermediates or in the cyclization of the 3' end of U6 snRNA (PMID: 9184239). Guanosine-2',3'-cyclic phosphate is capable of blocking DNA synthesis in vitro (PMID: 7528887). 2', 3'-cGMP seems to preferentially stimulate mature T-cells while 3', 5'-cGMP preferentially acts on B-cells (PMID: 163786)
Synonyms
  1. cyclic 2',3'-(hydrogen phosphate)-Guanosine
  2. 2',3'-Cyclic GMP
  3. 2',3' cGMP
  4. 2',3'-cGMP
Chemical IUPAC Name 2-amino-9-[(1R,2R,4R,5R)-7-hydroxy-4-(hydroxymethyl)-7-oxo-3,6,8-trioxa-7$l^{5}-phosphabicyclo[3.3.0]octan-2-yl]-3H-purin-6-one
Chemical Formula C10H12N5O7P
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
—
Class
—
Sub Class
—
Family
  • Mammalian Metabolite
Species
  • primary alcohol
  • primary amine
  • primary aromatic amine
  • oxo(het)arene
  • phosphoric acid ester
  • aromatic compound
  • heterocyclic compound
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 345.205
Monoisotopic Molecular Weight 345.047424
Isomeric SMILES NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](CO)[C@H]2OP(O)(=O)O[C@@H]12
Canonical SMILES NC1=NC(=O)C2=C(N1)N(C=N2)C1OC(CO)C2OP(O)(=O)OC12
KEGG Compound ID C06194 Link Image
BioCyc ID CPD-3709 Link Image
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11629 Link Image
Metagene Link HMDB11629 Link Image
METLIN ID Not Available
PubChem Compound 92823 Link Image
PubChem Substance 8444 Link Image
ChEBI ID Not Available
CAS Registry Number 15718-49-7
InChI Identifier InChI=1/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-6-5(3(1-16)20-9)21-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 3.53 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -1.61 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Not Available
Not Available
Predicted 13C NMR Spectrum Not Available
Not Available
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 Link Image map00230 Link Image
General References Not Available
Metabolic Enzymes
  1. 2',3'-cyclic-nucleotide 3'-phosphodiesterase
Enzyme 1 [top]
Enzyme 1 ID 7922
Enzyme 1 Name 2',3'-cyclic-nucleotide 3'-phosphodiesterase
Enzyme 1 Synonyms
  1. CNP
  2. CNPase
Enzyme 1 Gene Name CNP
Enzyme 1 Protein Sequence >2',3'-cyclic-nucleotide 3'-phosphodiesterase 
MNRGFSRKSHTFLPKIFFRKMSSSGAKDKPELQFPFLQDEDTVATLLECKTLFILRGLPG
SGKSTLARVIVDKYRDGTKMVSADAYKITPGARGAFSEEYKRLDEDLAAYCRRRDIRILV
LDDTNHERERLEQLFEMADQYQYQVVLVEPKTAWRLDCAQLKEKNQWQLSADDLKKLKPG
LEKDFLPLYFGWFLTKKSSETLRKAGQVFLEELGNHKAFKKELRQFVPGDEPREKMDLVT
YFGKRPPGVLHCTTKFCDYGKAPGAEEYAQQDVLKKSYSKAFTLTISALFVTPKTTGARV
ELSEQQLQLWPSDVDKLSPTDNLPRGSRAHITLGCAADVEAVQTGLDLLEILRQEKGGSR
GEEVGELSRGKLYSLGNGRWMLTLAKNMEVRAIFTGYYGKGKPVPTQGSRKGGALQSCTI
I
Enzyme 1 Number of Residues 421
Enzyme 1 Molecular Weight 47578.2
Enzyme 1 Theoretical pI 9.50
Enzyme 1 GO Classification
Function
  • 2',3'-cyclic-nucleotide 3'-phosphodiesterase activity
  • ATP binding
  • adenyl nucleotide binding
  • adenyl ribonucleotide binding
  • binding
  • catalytic activity
  • cyclic-nucleotide phosphodiesterase activity
  • hydrolase activity
  • hydrolase activity, acting on ester bonds
  • nucleoside binding
  • phosphoric diester hydrolase activity
  • phosphoric ester hydrolase activity
  • purine nucleoside binding
Process
  • RNA metabolic process
  • cell killing
  • cellular macromolecule metabolic process
  • cellular nitrogen compound metabolic process
  • cyclic nucleotide catabolic process
  • macromolecule metabolic process
  • metabolic process
  • nitrogen compound metabolic process
  • nucleobase, nucleoside and nucleotide metabolic process
  • nucleobase, nucleoside, nucleotide and nucleic acid metabolic process
  • nucleoside monophosphate catabolic process
  • nucleoside monophosphate metabolic process
  • nucleoside phosphate metabolic process
  • nucleotide metabolic process
Component
  • cell part
  • intracellular
  • membrane
Enzyme 1 General Function Involved in 2',3'-cyclic-nucleotide 3'-phosphodiesterase activity
Enzyme 1 Specific Function Nucleoside 2',3'-cyclic phosphate + H(2)O = nucleoside 2'-phosphate
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions
  • nucleoside 2',3'-cyclic phosphate + H2O = nucleoside 2'-phosphate [RN:R03422]
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 94721261 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID P09543 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name CN37_HUMAN Link Image
Enzyme 1 PDB ID 1WOJ Link Image
Enzyme 1 PDB File Show
Enzyme 1 3D Structure
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1266 bp 
ATGAACAGAGGCTTCTCCCGAAAAAGCCACACATTCCTGCCCAAGATCTTCTTCCGCAAG
ATGTCATCCTCAGGGGCCAAGGACAAGCCTGAGCTGCAGTTTCCCTTCCTTCAGGATGAG
GACACAGTGGCCACGCTGCTAGAGTGCAAGACGCTCTTCATCTTGCGCGGCCTGCCAGGA
AGCGGCAAGTCCACGCTGGCACGGGTCATCGTGGACAAGTACCGTGATGGCACCAAGATG
GTGTCGGCTGACGCTTACAAGATCACCCCCGGCGCTCGAGGAGCCTTCTCCGAGGAGTAC
AAGCGGCTCGATGAGGACCTGGCTGCCTACTGCCGCCGCCGGGACATCAGAATTCTTGTG
CTTGATGACACCAACCACGAACGGGAACGGCTGGAGCAGCTCTTTGAAATGGCCGACCAG
TACCAGTACCAGGTGGTGCTGGTGGAGCCCAAGACGGCGTGGCGGCTGGACTGTGCCCAG
CTCAAGGAGAAGAACCAGTGGCAGCTGTCGGCTGATGACCTGAAGAAGCTGAAGCCTGGG
CTGGAGAAGGACTTCCTGCCGCTCTACTTCGGCTGGTTCCTGACCAAGAAGAGCTCTGAG
ACCCTCCGCAAAGCCGGCCAGGTCTTCCTGGAAGAGCTGGGGAACCACAAGGCCTTCAAG
AAGGAGCTGCGACAATTCGTCCCTGGGGATGAGCCCAGGGAGAAGATGGACTTGGTCACC
TACTTTGGAAAGAGACCCCCAGGCGTGCTGCATTGCACAACCAAGTTTTGTGACTACGGG
AAGGCTCCCGGGGCAGAGGAGTACGCTCAACAAGATGTGTTAAAGAAATCTTACTCCAAG
GCCTTCACGCTGACCATCTCTGCCCTCTTTGTGACACCCAAGACGACTGGGGCCCGGGTG
GAGTTAAGCGAGCAGCAACTGCAGTTGTGGCCGAGTGATGTGGACAAGCTGTCACCCACT
GACAACCTGCCGCGGGGGAGCCGCGCCCACATCACCCTCGGCTGTGCAGCTGACGTAGAG
GCCGTGCAGACGGGCCTTGACCTCTTAGAGATTCTGCGGCAGGAGAAGGGGGGCAGCCGA
GGCGAGGAGGTGGGCGAGCTAAGCCGGGGCAAGCTCTATTCCTTGGGCAATGGGCGCTGG
ATGCTGACCCTGGCCAAGAACATGGAGGTCAGGGCCATCTTCACGGGGTACTACGGGAAA
GGCAAACCTGTGCCCACGCAAGGTAGCCGGAAGGGGGGCGCCTTGCAGTCCTGCACCATC
ATATGA
Enzyme 1 GenBank Gene ID NM_033133.4 Link Image
Enzyme 1 GeneCard ID CNP Link Image
Enzyme 1 GenAtlas ID CNP Link Image
Enzyme 1 HGNC ID HGNC:2158 Link Image
Enzyme 1 Chromosome Location 1
Enzyme 1 Locus 17q21
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Thompson RJ: 2',3'-cyclic nucleotide-3'-phosphohydrolase and signal transduction in central nervous system myelin. Biochem Soc Trans. 1992 Aug;20(3):621-6. [PubMed Link Image]
  2. Kurihara T, Takahashi Y, Nishiyama A, Kumanishi T: cDNA cloning and amino acid sequence of human brain 2',3'-cyclic-nucleotide 3'-phosphodiesterase. Biochem Biophys Res Commun. 1988 Apr 29;152(2):837-42. [PubMed Link Image]
  3. Monoh K, Kurihara T, Takahashi Y, Ichikawa T, Kumanishi T, Hayashi S, Minoshima S, Shimizu N: Structure, expression and chromosomal localization of the gene encoding human 2',3'-cyclic-nucleotide 3'-phosphodiesterase. Gene. 1993 Jul 30;129(2):297-301. [PubMed Link Image]
  4. Douglas AJ, Fox MF, Abbott CM, Hinks LJ, Sharpe G, Povey S, Thompson RJ: Structure and chromosomal localization of the human 2',3'-cyclic nucleotide 3'-phosphodiesterase gene. Ann Hum Genet. 1992 Jul;56(Pt 3):243-54. [PubMed Link Image]
  5. Zody MC, Garber M, Adams DJ, Sharpe T, Harrow J, Lupski JR, Nicholson C, Searle SM, Wilming L, Young SK, Abouelleil A, Allen NR, Bi W, Bloom T, Borowsky ML, Bugalter BE, Butler J, Chang JL, Chen CK, Cook A, Corum B, Cuomo CA, de Jong PJ, DeCaprio D, Dewar K, FitzGerald M, Gilbert J, Gibson R, Gnerre S, Goldstein S, Grafham DV, Grocock R, Hafez N, Hagopian DS, Hart E, Norman CH, Humphray S, Jaffe DB, Jones M, Kamal M, Khodiyar VK, LaButti K, Laird G, Lehoczky J, Liu X, Lokyitsang T, Loveland J, Lui A, Macdonald P, Major JE, Matthews L, Mauceli E, McCarroll SA, Mihalev AH, Mudge J, Nguyen C, Nicol R, O'Leary SB, Osoegawa K, Schwartz DC, Shaw-Smith C, Stankiewicz P, Steward C, Swarbreck D, Venkataraman V, Whittaker CA, Yang X, Zimmer AR, Bradley A, Hubbard T, Birren BW, Rogers J, Lander ES, Nusbaum C: DNA sequence of human chromosome 17 and analysis of rearrangement in the human lineage. Nature. 2006 Apr 20;440(7087):1045-9. [PubMed Link Image]
  6. Gerhard DS, Wagner L, Feingold EA, Shenmen CM, Grouse LH, Schuler G, Klein SL, Old S, Rasooly R, Good P, Guyer M, Peck AM, Derge JG, Lipman D, Collins FS, Jang W, Sherry S, Feolo M, Misquitta L, Lee E, Rotmistrovsky K, Greenhut SF, Schaefer CF, Buetow K, Bonner TI, Haussler D, Kent J, Kiekhaus M, Furey T, Brent M, Prange C, Schreiber K, Shapiro N, Bhat NK, Hopkins RF, Hsie F, Driscoll T, Soares MB, Casavant TL, Scheetz TE, Brown-stein MJ, Usdin TB, Toshiyuki S, Carninci P, Piao Y, Dudekula DB, Ko MS, Kawakami K, Suzuki Y, Sugano S, Gruber CE, Smith MR, Simmons B, Moore T, Waterman R, Johnson SL, Ruan Y, Wei CL, Mathavan S, Gunaratne PH, Wu J, Garcia AM, Hulyk SW, Fuh E, Yuan Y, Sneed A, Kowis C, Hodgson A, Muzny DM, McPherson J, Gibbs RA, Fahey J, Helton E, Ketteman M, Madan A, Rodrigues S, Sanchez A, Whiting M, Madari A, Young AC, Wetherby KD, Granite SJ, Kwong PN, Brinkley CP, Pearson RL, Bouffard GG, Blakesly RW, Green ED, Dickson MC, Rodriguez AC, Grimwood J, Schmutz J, Myers RM, Butterfield YS, Griffith M, Griffith OL, Krzywinski MI, Liao N, Morin R, Palmquist D, Petrescu AS, Skalska U, Smailus DE, Stott JM, Schnerch A, Schein JE, Jones SJ, Holt RA, Baross A, Marra MA, Clifton S, Makowski KA, Bosak S, Malek J: The status, quality, and expansion of the NIH full-length cDNA project: the Mammalian Gene Collection (MGC). Genome Res. 2004 Oct;14(10B):2121-7. [PubMed Link Image]
  7. Stricker R, Kalbacher H, Reiser G: The epitope recognized by a monoclonal antibody in the myelin-associated protein CNP. Biochem Biophys Res Commun. 1997 Aug 18;237(2):266-70. [PubMed Link Image]
  8. Basrur V, Yang F, Kushimoto T, Higashimoto Y, Yasumoto K, Valencia J, Muller J, Vieira WD, Watabe H, Shabanowitz J, Hearing VJ, Hunt DF, Appella E: Proteomic analysis of early melanosomes: identification of novel melanosomal proteins. J Proteome Res. 2003 Jan-Feb;2(1):69-79. [PubMed Link Image]
  9. Chi A, Valencia JC, Hu ZZ, Watabe H, Yamaguchi H, Mangini NJ, Huang H, Canfield VA, Cheng KC, Yang F, Abe R, Yamagishi S, Shabanowitz J, Hearing VJ, Wu C, Appella E, Hunt DF: Proteomic and bioinformatic characterization of the biogenesis and function of melanosomes. J Proteome Res. 2006 Nov;5(11):3135-44. [PubMed Link Image]
  10. Gauci S, Helbig AO, Slijper M, Krijgsveld J, Heck AJ, Mohammed S: Lys-N and trypsin cover complementary parts of the phosphoproteome in a refined SCX-based approach. Anal Chem. 2009 Jun 1;81(11):4493-501. [PubMed Link Image]
  11. Sakamoto Y, Tanaka N, Ichimiya T, Kurihara T, Nakamura KT: Crystal structure of the catalytic fragment of human brain 2',3'-cyclic-nucleotide 3'-phosphodiesterase. J Mol Biol. 2005 Feb 25;346(3):789-800. Epub 2005 Jan 12. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available