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Record Information
Version	2.0
Creation Date	2012-05-31 13:46:33 -0600
Update Date	2015-06-03 15:53:47 -0600
Secondary Accession Numbers	ECMDB01162
Identification
Name:	Heme O
Description	HemeOo is a member of the chemical class known as Metalloporphyrins. These are polycyclic compounds containing a porphyrin moiety and a metal atom. Heme O (or haem O) differs from the closely related heme A by having a methyl group at ring position 8 instead of the formyl group. The isoprenoid chain at position 2 is the same. Heme O, found in the bacterium Escherichia coli, functions in a similar manner to heme A in mammalian oxygen reduction. (WikiPedia)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb174c1b8> Close
Synonyms:	Heme O
Chemical Formula:	C49H58FeN4O5
Weight:	Average: 838.854 Monoisotopic: 838.375663119
InChI Key:	FISPASSVCDRERW-KVGORYHISA-L
InChI:	InChI=1S/C49H60N4O5.Fe/c1-10-35-31(6)40-26-45-49(46(54)19-13-18-30(5)17-12-16-29(4)15-11-14-28(2)3)34(9)41(53-45)24-38-32(7)36(20-22-47(55)56)43(51-38)27-44-37(21-23-48(57)58)33(8)39(52-44)25-42(35)50-40;/h10,14,16,18,24-27,46,54H,1,11-13,15,17,19-23H2,2-9H3,(H4,50,51,52,53,55,56,57,58);/q;+2/p-2/b29-16+,30-18+,38-24-,39-25-,40-26-,41-24-,42-25-,43-27-,44-27-,45-26-;
CAS number:	137397-56-9
IUPAC Name:	3-[(11Z,16Z)-20-(2-carboxyethyl)-15-ethenyl-10-[(4E,8E)-1-hydroxy-5,9,13-trimethyltetradeca-4,8,12-trien-1-yl]-5,9,14,19-tetramethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1(20),2,4,6(25),7,9,11,13(24),14,16,18-undecaen-4-yl]propanoic acid
Traditional IUPAC Name:	3-[(11Z,16Z)-20-(2-carboxyethyl)-15-ethenyl-10-[(4E,8E)-1-hydroxy-5,9,13-trimethyltetradeca-4,8,12-trien-1-yl]-5,9,14,19-tetramethyl-21,23,24,25-tetraaza-22-ferrahexacyclo[9.9.3.1³,⁶.1¹³,¹⁶.0⁸,²³.0¹⁸,²¹]pentacosa-1(20),2,4,6(25),7,9,11,13(24),14,16,18-undecaen-4-yl]propanoic acid
SMILES:	CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(O)C1=C(C)/C2=C/C3=N/C(=C\C4=C(CCC(O)=O)C(C)=C5/C=C6\N=C(\C=C\1/N\2[Fe]N45)C(C)=C6C=C)/C(CCC(O)=O)=C3C
Chemical Taxonomy
Description	belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom.
Kingdom	Organic compounds
Super Class	Organoheterocyclic compounds
Class	Tetrapyrroles and derivatives
Sub Class	Metallotetrapyrroles
Direct Parent	Metallotetrapyrroles
Alternative Parents	Not Available
Substituents	Not Available
Molecular Framework	Not Available
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 0.0057 g/L ALOGPS logP 6.21 ALOGPS logP 11.26 ChemAxon logS -5.2 ALOGPS pKa (Strongest Acidic) 3.65 ChemAxon pKa (Strongest Basic) 2.84 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 130.47 Ų ChemAxon Rotatable Bond Count 17 ChemAxon Refractivity 237.91 m³·mol⁻¹ ChemAxon Polarizability 96.53 ų ChemAxon Number of Rings 6 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:	Farnesyl pyrophosphate + Water + Heme > Heme O + Pyrophosphate Heme + Water + Farnesyl pyrophosphate <> Heme O + Pyrophosphate ferroheme b + Water + Farnesyl pyrophosphate + Farnesyl pyrophosphate > Heme O + Pyrophosphate Farnesyl pyrophosphate + Water + Heme > Heme O + Pyrophosphate Farnesyl pyrophosphate + Water + Heme > Heme O + Pyrophosphate
SMPDB Pathways:	Oxidative phosphorylation PW000919 Porphyrin metabolism PW000936
KEGG Pathways:	Oxidative phosphorylation ec00190 Porphyrin and chlorophyll metabolism ec00860
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-009l-0000000970-0ab5b5c8236aeb83353a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-00s6-1200001930-2056d7e5ba2335a6154b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0159-1100000900-fb1e1bfe680d13bc4e01 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-0000000390-fc9d0bdfd86ce5bb111e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0171-2120061950-c114e5cb2af8c6ea5b24 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00fs-0000090410-19e8eef5041c9549ea3f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000i-0000000090-46c44cfe9d493547a919 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-00ri-0100002790-aa7b2dbeb177907521b7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00g0-0000024930-47277d8050776dbaab1c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0079-2000001690-d482b755c66f4c96c8d0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-003s-6200006910-8a7a86584f45027cc939 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-067j-8400009320-337b466a95de04a44a14 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:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 24480 HMDB ID HMDB01162 Pubchem Compound ID 23724534 Kegg ID C15672 ChemSpider ID 3571849 Wikipedia Heme O BioCyc ID HEME_O EcoCyc ID HEME_O

Enzymes