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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-02-04 10:38:54 UTC
Update Date2020-02-26 21:35:37 UTC
HMDB IDHMDB0011680
Secondary Accession Numbers
  • HMDB11680
Metabolite Identification
Common NameInosine 2',3'-cyclic phosphate
DescriptionCoproporphyrinogen I belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure. Coproporphyrinogen I is a weakly acidic compound (based on its pKa). Coproporphyrinogen I exists in all living species, ranging from bacteria to humans. In humans, coproporphyrinogen I is involved in the metabolic disorder called the acute intermittent porphyria pathway. A large number of factors are capable of increasing porphyrin excretion, owing to different and multiple causes and etiologies: (1) the main site of the chronic hepatic porphyria disease process concentrates on the liver, (2) a functional and morphologic liver injury is almost regularly associated with this chronic porphyria, and (3) the toxic form due to occupational and environmental exposure takes mainly a subclinical course. Hepatic porphyrias are characterized by acute neurological attacks (seizures, psychosis, extreme back and abdominal pain, and an acute polyneuropathy), while the erythropoietic forms present with skin problems (usually a light-sensitive blistering rash and increased hair growth). Outside of the human body, Coproporphyrinogen I has been detected, but not quantified in, several different foods, such as pak choy, pepper (c. chinense), tea leaf willows, rosemaries, and mung beans. This could make coproporphyrinogen I a potential biomarker for the consumption of these foods. A neurotoxin causes damage to nerve cells and nerve tissues. Coproporphyrinogen I is a porphyrin metabolite arising from heme synthesis. Coproporphyrinogen I is biosynthesized from the tetrapyrrole hydroxymethylbilane, which is converted by the action of uroporphyrinogen synthase to uroporphyrinogen I. Uroporphyrinogen I is subsequently converted into coproporphyrinogen I through a series of four decarboxylations. Decreased biliary excretion of coproporphyrin leading to a compensatory urinary excretion. Coproporphyrinogen I can be found in a number of food items, including cascade huckleberry, hyacinth bean, horseradish tree, and watercress.
Structure
Data?1582752937
Synonyms
ValueSource
3,8,13,18-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropionic acidChEBI
COPROPORPHYRIN IChEBI
3,8,13,18-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropionateGenerator
3,8,13,18-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropanoateHMDB
3,8,13,18-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropanoic acidHMDB
2',3' Cyclic impHMDB
Inosine cyclic 2',3'-(hydrogen phosphate)HMDB
Inosine cyclic 2',3'-monophosphateHMDB
Inosine cyclic 2,3 monophosphateHMDB
Inosine cyclic-2',3'-monophosphateHMDB
2',3'-Cyclic impMeSH, HMDB
Inosine 2',3'-cyclic phosphoric acidGenerator
Chemical FormulaC10H11N4O7P
Average Molecular Weight330.1907
Monoisotopic Molecular Weight330.036535238
IUPAC Name9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-6,9-dihydro-3H-purin-6-one
Traditional Name9-[(3aR,4R,6R,6aR)-2-hydroxy-6-(hydroxymethyl)-2-oxo-tetrahydro-2λ⁵-furo[3,4-d][1,3,2]dioxaphosphol-4-yl]-3H-purin-6-one
CAS Registry Number15569-30-9
SMILES
OC[C@H]1O[C@H]([C@@H]2OP(O)(=O)O[C@H]12)N1C=NC2=C1NC=NC2=O
InChI Identifier
InChI=1S/C10H11N4O7P/c15-1-4-6-7(21-22(17,18)20-6)10(19-4)14-3-13-5-8(14)11-2-12-9(5)16/h2-4,6-7,10,15H,1H2,(H,17,18)(H,11,12,16)/t4-,6-,7-,10-/m1/s1
InChI KeySBJVDTBACUMFFD-KQYNXXCUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as porphyrins. Porphyrins are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassPorphyrins
Direct ParentPorphyrins
Alternative Parents
Substituents
  • Porphyrin
  • Tetracarboxylic acid or derivatives
  • Substituted pyrrole
  • Pyrrole
  • Heteroaromatic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

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 Solubility2.71 g/LALOGPS
logP-1.1ALOGPS
logP-2.2ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.72ChemAxon
pKa (Strongest Basic)2.78ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area144.5 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity67.99 m³·mol⁻¹ChemAxon
Polarizability27.57 ųChemAxon
Number of Rings4ChemAxon
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, Positivesplash10-00di-2932000000-458fe2cf018cce0f0996Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5973000000-e313786e70931a68f57dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1904000000-96a65d98a5cef1b1b6d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-e9165df1ed565032651dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-0e4749b1ba78def64d0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-0409000000-140ae7be2ac50fd17709Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-6abb145404ebbca6a0d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-3900000000-7a8546fa0e738304520eSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022874
KNApSAcK IDNot Available
Chemspider ID389645
KEGG Compound IDC05768
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCoproporphyrinogen I
METLIN ID6516
PubChem Compound440776
PDB IDNot Available
ChEBI ID28607
Food Biomarker OntologyNot Available
VMH IDCPPPG1
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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