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Record Information
Version	2.0
Creation Date	2012-05-31 13:48:33 -0600
Update Date	2015-06-03 15:53:53 -0600
Secondary Accession Numbers	ECMDB01261
Identification
Name:	Coproporphyrinogen III
Description	In the metabolism of porphyrin, the enzyme uroporphyrinogen III decarboxylase generates coproporphyrinogen III from uroporphyrinogen III, and coproporphyrinogen III oxidase converts it into protoporphyrinogen IX. (Wikipedia)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa9ec049c> Close
Synonyms:	3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoate 3,8,13,17-Tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,7,12,18-tetrapropanoic acid 5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-2,7,12,18-Porphinetetrapropionate 5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-2,7,12,18-Porphinetetrapropionic acid 5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-21H,23H-Porphine-2,7,12,18-tetrapropanoate 5,10,15,20,22,24-Hexahydro-3,8,13,17-tetramethyl-21H,23H-Porphine-2,7,12,18-tetrapropanoic acid CoPorgen III Coproporphyrinogen Coproporphyrinogen I Coproporphyrinogen-III
Chemical Formula:	C36H44N4O8
Weight:	Average: 660.7566 Monoisotopic: 660.315914404
InChI Key:	NIUVHXTXUXOFEB-UHFFFAOYSA-N
InChI:	InChI=1S/C36H44N4O8/c1-17-21(5-9-33(41)42)29-14-27-19(3)22(6-10-34(43)44)30(39-27)15-28-20(4)24(8-12-36(47)48)32(40-28)16-31-23(7-11-35(45)46)18(2)26(38-31)13-25(17)37-29/h37-40H,5-16H2,1-4H3,(H,41,42)(H,43,44)(H,45,46)(H,47,48)
CAS number:	2624-63-7
IUPAC Name:	3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid
Traditional IUPAC Name:	3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid
SMILES:	CC1=C2CC3=C(C)C(CCC(O)=O)=C(CC4=C(CCC(O)=O)C(C)=C(CC5=C(CCC(O)=O)C(C)=C(CC(N2)=C1CCC(O)=O)N5)N4)N3
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.
Kingdom	Organic compounds
Super Class	Organoheterocyclic compounds
Class	Tetrapyrroles and derivatives
Sub Class	Porphyrins
Direct Parent	Porphyrins
Alternative Parents	Tetracarboxylic acids and derivatives Substituted pyrroles Heteroaromatic compounds Carboxylic acids Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
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	coproporphyrinogen (CHEBI:15439 )
Physical Properties
State:	Solid
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.011 g/L ALOGPS logP 1.96 ALOGPS logP 4.89 ChemAxon logS -4.8 ALOGPS pKa (Strongest Acidic) 3.8 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 8 ChemAxon Hydrogen Donor Count 8 ChemAxon Polar Surface Area 212.36 Ų ChemAxon Rotatable Bond Count 12 ChemAxon Refractivity 181.86 m³·mol⁻¹ ChemAxon Polarizability 72.85 ų ChemAxon Number of Rings 5 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Membrane
Reactions:	Coproporphyrinogen III + S-Adenosylmethionine > Protoporphyrinogen IX + Carbon dioxide + L-Methionine + 5'-Deoxyadenosine Coproporphyrinogen III + Oxygen + Hydrogen ion > Protoporphyrinogen IX + Carbon dioxide + Water Hydrogen ion + Uroporphyrinogen III > Carbon dioxide + Coproporphyrinogen III Uroporphyrinogen III > Coproporphyrinogen III +4 Carbon dioxide Coproporphyrinogen III + Oxygen + 2 Hydrogen ion > Protoporphyrinogen IX +2 Carbon dioxide +2 Water Coproporphyrinogen III + 2 S-adenosyl-L-methionine > Protoporphyrinogen IX +2 Carbon dioxide +2 L-Methionine +2 5'-Deoxyadenosine Uroporphyrinogen III + 4 Hydrogen ion >4 Carbon dioxide + Coproporphyrinogen III S-adenosyl-L-methionine + Coproporphyrinogen III > 5'-Deoxyadenosine + L-Methionine + Carbon dioxide + Protoporphyrinogen IX
SMPDB Pathways:	Porphyrin metabolism PW000936
KEGG Pathways:	Porphyrin and chlorophyll metabolism ec00860
EcoCyc Pathways:	heme biosynthesis from uroporphyrinogen-III I HEME-BIOSYNTHESIS-II heme biosynthesis from uroporphyrinogen-III II HEMESYN2-PWY superpathway of heme biosynthesis from uroporphyrinogen-III PWY0-1415
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0uxu-1000029000-41e3094ebb1945eeb049 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-002f-0000049000-0387f74262a47cf81121 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-05mn-0000095000-92704e3251119447de7c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-0000190000-117c439eaa250aa4b3b3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-002f-0000049000-0387f74262a47cf81121 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-05mn-0000095000-92704e3251119447de7c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-0000190000-117c439eaa250aa4b3b3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-052f-0000029000-96c0bca58c9caf08416f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-052g-1000079000-1da57e7f8a138a6c5516 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-052g-7000097000-2c52075e18d7d944ae80 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-052f-0000029000-96c0bca58c9caf08416f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-052g-1000079000-1da57e7f8a138a6c5516 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-052g-7000097000-2c52075e18d7d944ae80 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0a4l-0000019000-0ab4e0263cb7a6f3f8ff View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-05te-0000096000-dbcc904bd06bb15770cf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-014i-0000090000-873dcdb0fbed0fef5d75 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0006-0000019000-5432645efaaa860e5770 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-003u-0000098000-e73b7cc718729b01bbe4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00kb-1000092000-b034ed98f0385ea7fadb View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Shoolingin-Jordan, Peter M. The biosynthesis of coproporphyrinogen III. Porphyrin Handbook (2003), 12 33-74.
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15439 HMDB ID HMDB01261 Pubchem Compound ID 321 Kegg ID C03263 ChemSpider ID 315 Wikipedia Coproporphyrinogen III BioCyc ID COPROPORPHYRINOGEN_III EcoCyc ID COPROPORPHYRINOGEN_III Ligand Expo CP3

Enzymes