Record Information
Version3.6
Creation Date2009-07-25 00:10:23 UTC
Update Date2013-02-08 18:40:29 UTC
HMDB IDHMDB12947
Secondary Accession NumbersNone
Metabolite Identification
Common NameFerrocytochrome
DescriptionFerricytochrome is a cytochrome containing reduced (ferrous) iron. Cytochrome c is an electron-carrying protein found in mitochondria of all aerobic organisms. It is part of the terminal oxidation chain, which completes the breakdown of foods to COZ and HzO, storing the liberated chemical energy in molecules of ATP. Like myoglobin, it is an iron porphyrin protein, made up of one heme group and one polypeptide chain. The iron atomalternates between the +2 and +3 oxidation state as the molecule interacts in turn with cytochrome reductase and cytochrome oxidase, each a large multimolecular complex (l-3). One of the goals of the present x-ray analysis is to understand how electron. transfer occurs into and out of cytochrome c, which will ultimately require a knowledge of the molecular structure in both the ferric and ferrous states.
Structure
Thumb
Synonyms
  1. 553-12-8 (FREE ACID)
  2. Ferrocytochrome b-561
  3. H2ppIX
  4. HEM
  5. Kammerer'S porphyrin
  6. Kammerer'S prophyrin
  7. Lopac-P-8293
  8. NSC2632 (FREE ACID)
  9. Ooporphyrin
  10. Porphyrinogen ix
  11. PP-ix
  12. Protoporhyrin ix
  13. Protoporphyrin
  14. Protoporphyrin (PP)
  15. Protoporphyrin ix
  16. Protoporphyrin IX (6CI)
  17. Protoporphyrin IX (van)
  18. Protoporphyrin IX disodium
  19. Protoporphyrin-1x
  20. Protoporpyrin ix
Chemical FormulaC33H32FeN4O4
Average Molecular Weight604.477
Monoisotopic Molecular Weight604.177297665
IUPAC Name4,20-bis(2-carboxyethyl)-10-ethenyl-5,9,14,15,19-pentamethyl-2$l^{4},22,23$l^{4},25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-1,1-diuide
Traditional IUPAC Name4,20-bis(2-carboxyethyl)-10-ethenyl-5,9,14,15,19-pentamethyl-2$l^{4},22,23$l^{4},25-tetraaza-1-ferraoctacyclo[11.9.1.1^{1,8}.1^{3,21}.0^{2,6}.0^{16,23}.0^{18,22}.0^{11,25}]pentacosa-2,4,6,8,10,12,14,16(23),17,19,21(24)-undecaene-1,1-diuide
CAS Registry Number1818-68-4
SMILES
CC1=C(CCC(O)=O)C2=CC3=[N]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C)C8=[N]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=O
InChI Identifier
InChI=1S/C33H34N4O4.Fe/c1-7-21-18(4)26-13-28-20(6)23(9-11-33(40)41)31(37-28)15-30-22(8-10-32(38)39)19(5)27(36-30)12-24-16(2)17(3)25(34-24)14-29(21)35-26;/h7,12-15H,1,8-11H2,2-6H3,(H4,34,35,36,37,38,39,40,41);/p-2/b24-12-,25-14?,26-13-,27-12-,28-13-,29-14?,30-15-,31-15-;
InChI KeyKASOULBHUXQGJC-NHCNHRESSA-L
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassTetrapyrroles and Derivatives
Sub ClassMetallotetrapyrroles
Other Descriptors
  • Organic Compounds
  • Porphyrins
Substituents
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Organic Transition Metal Moeity
  • Organometallic Compound
  • Pyrrole
  • Quaternary Ammonium Salt
Direct ParentMetalloporphyrins
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 solubility0.15 g/LALOGPS
logP1.19ALOGPS
logS-3.6ALOGPS
physiological charge-2ChemAxon
hydrogen acceptor count0ChemAxon
hydrogen donor count0ChemAxon
polar surface area121.19ChemAxon
rotatable bond count7ChemAxon
refractivity171.54ChemAxon
polarizability68.6ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029223
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05183
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB12947
Metagene LinkHMDB12947
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15910
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gederaas OA, Berg K, Romslo I: A comparative study of normal and reverse phase high pressure liquid chromatography for analysis of porphyrins accumulated after 5-aminolaevulinic acid treatment of colon adenocarcinoma cells. Cancer Lett. 2000 Mar 31;150(2):205-13. Pubmed: 10704744
  2. Desuzinges-Mandon E, Arnaud O, Martinez L, Huche F, Di Pietro A, Falson P: ABCG2 transports and transfers heme to albumin through its large extracellular loop. J Biol Chem. 2010 Oct 22;285(43):33123-33. doi: 10.1074/jbc.M110.139170. Epub 2010 Aug 12. Pubmed: 20705604
  3. Han I, Jun MS, Kim SK, Kim M, Kim JC: Expression pattern and intensity of protoporphyrin IX induced by liposomal 5-aminolevulinic acid in rat pilosebaceous unit throughout hair cycle. Arch Dermatol Res. 2005 Nov;297(5):210-7. Epub 2005 Nov 11. Pubmed: 16231146
  4. Schumacher A, Wafula PO, Teles A, El-Mousleh T, Linzke N, Zenclussen ML, Langwisch S, Heinze K, Wollenberg I, Casalis PA, Volk HD, Fest S, Zenclussen AC: Blockage of heme oxygenase-1 abrogates the protective effect of regulatory T cells on murine pregnancy and promotes the maturation of dendritic cells. PLoS One. 2012;7(8):e42301. doi: 10.1371/journal.pone.0042301. Epub 2012 Aug 10. Pubmed: 22900010

Enzymes

Gene Name:
CYB5R3
Uniprot ID:
P00387
Gene Name:
SQLE
Uniprot ID:
Q14534
Gene Name:
POR
Uniprot ID:
P16435