Record Information
Version1.0
Creation date2011-09-21 00:09:20 UTC
Update date2015-10-09 22:30:53 UTC
Primary IDFDB022159
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCoproporphyrin I
DescriptionCoproporhyrin I is a porphyrin metabolite arising from heme synthesis. Porphyrins are pigments found in both animal and plant life. Coproporphyrin I is a tetrapyrrole dead-end product from the spontaneous oxidation of the methylene bridges of coproporphynogen, arising from heme synthesis and secreted in feces and urine. Increased levels of coproporphyrins can indicate congenital erythropoietic porphyria or sideroblastic anaemia. Porphyria is a pathological state characterised by abnormalities of porphyrin metabolism and results in the excretion of large quantities of porphyrins in the urine and in extreme sensitivity to light. 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, 3) the toxic form due to occupational and environmental exposure takes mainly a subclinical course. Hepatic factors includes disturbance in coproporphyrinogen metabolism, which results from inhibition of coproporphyrinogen oxidase as well as from the rapid loss from, and diminished utilization of coproporphyrinogen in the hepatocytes, which may also explain why coproporphyrin, its autoxidation product, predominates physiologically in the urine; decreased biliary excretion of coproporphyrin leading to a compensatory urinary excretion, so that the coproporphyrin ring isomer ratio (1:III) becomes a sensitive index for impaired liver function and intrahepatic cholestasis; and disturbed activity of hepatic uroporphyrinogen decarboxylase. In itself, secondary coproporphyrinuria is not associated with porphyria symptoms of a hepatologic-gastroenterologic, neurologic, or dermatologic order, even though coproporphyrinuria can occur with such symptoms. (PMID: 3327428) [HMDB]
CAS Number531-14-6
Structure
Thumb
Synonyms
SynonymSource
3,8,13,17-Tetramethylporphyrin-2,7,12,18-tetrapropanoic acidChEBI
3,8,13,17-Tetramethylporphyrin-2,7,12,18-tetrapropanoateGenerator
3,8,13,18-Tetramethyl-2,7,12,17-porphinetetrapropionateHMDB
3,8,13,18-Tetramethyl-2,7,12,17-porphinetetrapropionic acidHMDB
3,8,13,18-Tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionateHMDB
3,8,13,18-Tetramethyl-21H,23H-porphine-2,7,12,17-tetrapropionic acidHMDB
3,8,13,18-tetramethyl-2,7,12,17-Porphinetetrapropionatehmdb
3,8,13,18-tetramethyl-2,7,12,17-Porphinetetrapropionic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.031 g/LALOGPS
logP2.53ALOGPS
logP5ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)3.56ChemAxon
pKa (Strongest Basic)5.18ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area206.56 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity176.26 m³·mol⁻¹ChemAxon
Polarizability74.04 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC36H38N4O8
IUPAC name3-[9,14,19-tris(2-carboxyethyl)-5,10,15,20-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),2,4,6(24),7,9,11,13(22),14,16,18-undecaen-4-yl]propanoic acid
InChI IdentifierInChI=1S/C36H38N4O8/c1-17-21(5-9-33(41)42)29-14-26-19(3)23(7-11-35(45)46)31(39-26)16-28-20(4)24(8-12-36(47)48)32(40-28)15-27-18(2)22(6-10-34(43)44)30(38-27)13-25(17)37-29/h13-16,37,40H,5-12H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/b25-13-,26-14-,27-15-,28-16-,29-14-,30-13-,31-16-,32-15-
InChI KeyVORBHEGMEBOMMB-JRHDEHKPSA-N
Isomeric SMILESCC1=C(CCC(O)=O)/C2=C/C3=N/C(=C\C4=C(C)C(CCC(O)=O)=C(N4)/C=C4\N=C(\C=C\1/N\2)C(CCC(O)=O)=C4C)/C(CCC(O)=O)=C3C
Average Molecular Weight654.7089
Monoisotopic Molecular Weight654.268964212
Classification
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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052g-2000069000-b0400ff816c8bb479aa9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0000039000-f3b4207c1c84e6625cb5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4u-0000097000-25bf85caccefc18e4e75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ot-1000090000-f4fcb2a24b23cd617b5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000009000-9d1a49bb4b1cf969e8e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg0-1000039000-f24da7ff41769ba0e5beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000042000-ef49befaf8862d948c2bView in MoNA
ChemSpider ID16736701
ChEMBL IDNot Available
KEGG Compound IDC05769
Pubchem Compound ID68271
Pubchem Substance IDNot Available
ChEBI ID28421
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00643
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET ID1R3Q
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Porphyrin MetabolismSMP00024 map00860
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference