coproporphyrinogen I (PAMDB120047)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120047
Identification
Name: coproporphyrinogen I
Description:The cyclic tetrapyrrole anion formed by loss of a proton from each of the four carboxy groups of coproporphyrinogen I.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 3,3',3'',3'''-(3,8,13,18-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrayl)tetrapropanoate
  • 3,8,13,18-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropionate
  • coproporphyrinogen I
Chemical Formula: C36H40N4O8
Average Molecular Weight: 656.734
Monoisotopic Molecular Weight: 660.3159
InChI Key: WIUGGJKHYQIGNH-UHFFFAOYSA-J
InChI:InChI=1S/C36H44N4O8/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/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)/p-4
CAS number: 31110-56-2
IUPAC Name:3,8,13,18-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,17-tetrapropanoate
Traditional IUPAC Name: coproporphyrinogen I
SMILES:CC1(=C2(CC5(=C(CCC([O-])=O)C(C)=C(CC4(=C(CCC([O-])=O)C(C)=C(CC3(=C(CCC([O-])=O)C(C)=C(CC(=C(CCC([O-])=O)1)N2)N3))N4))N5)))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as porphyrins. These are compounds containing a fundamental skeleton of four pyrrole nuclei united through the alpha-positions by four methine groups to form a macrocyclic structure.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassTetrapyrroles and derivatives
Direct Parent Porphyrins
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 Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: 171 - 174 °C
Experimental Properties:
PropertyValueReference
Melting Point171 - 174 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 mg/mLALOGPS
logP1.97ALOGPS
logP4.89ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.85ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area212.36 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity181.86 m3·mol-1ChemAxon
Polarizability71.34 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
uroporphyrinogen-I + Hydrogen ion → coproporphyrinogen I + Carbon dioxide
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ox-0000029000-7cfed66d72503c62d69fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07c7-0000098000-c52b6ccc51ad35ceecd9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0102190000-338272475aad39d99e29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000009000-68fb68abaac4161fb473View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1000029000-03bf0dcb10bc9f0283a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000043000-4a0f162250fd839a83b3View in MoNA
References
References:
  • Ding Y, Lin B, Huie CW: Binding studies of porphyrins to human serum albumin using affinity capillary electrophoresis. Electrophoresis. 2001 Jul;22(11):2210-6. [11504054 ]
  • Gorchein A, Guo R, Lim CK, Raimundo A, Pullon HW, Bellingham AJ: Porphyrins in urine, plasma, erythrocytes, bile and faeces in a case of congenital erythropoietic porphyria (Gunther's disease) treated with blood transfusion and iron chelation: lack of benefit from oral charcoal. Biomed Chromatogr. 1998 Nov-Dec;12(6):350-6. [9861496 ]
  • Beukeveld GJ, In 't Veld G, Havinga R, Groen AK, Wolthers BG, Kuipers F: Relationship between biliary lipid and protoporphyrin secretion; potential role of mdr2 P-glycoprotein in hepatobiliary organic anion transport. J Hepatol. 1996 Mar;24(3):343-52. [8778203 ]
  • Pinelli A, Mussini C, Bertolini B, Buratti M, Trivulzio S: Increased excretion of urine coproporphyrins during daunorubicin administration in patients affected by acute myelogenous leukemia. Pharmacol Res. 2003 Nov;48(5):515-8. [12967599 ]
  • Sakai T, Niinuma Y, Yanagihara S, Ushio K: Liquid-chromatographic separation and determination of coproporphyrins I and III in urine. Clin Chem. 1983 Feb;29(2):350-3. [6821943 ]
  • Cornford P: Transformation of porphobilinogen into porphyrins by preparations from human erythrocytes. Biochem J. 1964 Apr;91(1):64-73. [5833390 ]
  • Pannier E, Viot G, Aubry MC, Grange G, Tantau J, Fallet-Bianco C, Muller F, Cabrol D: Congenital erythropoietic porphyria (Gunther's disease): two cases with very early prenatal manifestation and cystic hygroma. Prenat Diagn. 2003 Jan;23(1):25-30. [12533808 ]
  • Mel'nikova YaI, Kravchuk ZI, Preygerzon VA, Martsev SP: Functional activation of antibodies on modification with Pd(II) coproporphyrin I N-Hydroxysuccinimide ester. Biochemistry (Mosc). 1997 Aug;62(8):924-7. [9360305 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
HMDBHMDB02158
CHEMSPIDER20171594
CHEBI62631
PUBCHEM20849147
LIGAND-CPDC05768