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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:59:35 UTC
HMDB IDHMDB0001162
Secondary Accession Numbers
  • HMDB01162
Metabolite Identification
Common NameHeme O
DescriptionHeme O belongs to the class of organic compounds known as metallotetrapyrroles. These are polycyclic compounds containing a tetrapyrrole skeleton combined with a metal atom. Heme O is a moderately basic compound (based on its pKa). Heme O exists in all living species, ranging from bacteria to humans. In humans, heme O is involved in the metabolic disorder called congenital erythropoietic porphyria (cep) or gunther disease pathway. Heme O, found in the bacterium Escherichia coli, functions in a similar manner to heme A in mammalian oxygen reduction. The isoprenoid chain at position 2 is the same. 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.
Structure
Data?1582752180
SynonymsNot Available
Chemical FormulaC49H58FeN4O5
Average Molecular Weight838.854
Monoisotopic Molecular Weight838.375663119
IUPAC Name3-[(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 Name3-[(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
CAS Registry Number137397-56-9
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
InChI Identifier
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-;
InChI KeyFISPASSVCDRERW-KVGORYHISA-L
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassMetallotetrapyrroles
Direct ParentMetallotetrapyrroles
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkNot Available
External DescriptorsNot Available
Ontology
Physiological effect

Adverse health effect

Disposition

Source

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0057 g/LALOGPS
logP6.21ALOGPS
logP11.26ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)3.65ChemAxon
pKa (Strongest Basic)2.84ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area130.47 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity237.91 m³·mol⁻¹ChemAxon
Polarizability96.53 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+284.01232859911
AllCCS[M-H]-273.25132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Heme OCC(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)=C3C8298.5Standard polar33892256
Heme OCC(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)=C3C4564.4Standard non polar33892256
Heme OCC(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)=C3C6267.6Semi standard non polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heme O 10V, Positive-QTOFsplash10-009l-0000000970-0ab5b5c8236aeb83353a2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heme O 20V, Positive-QTOFsplash10-00s6-1200001930-2056d7e5ba2335a6154b2015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heme O 40V, Positive-QTOFsplash10-0159-1100000900-fb1e1bfe680d13bc4e012015-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heme O 10V, Negative-QTOFsplash10-000i-0000000390-fc9d0bdfd86ce5bb111e2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heme O 20V, Negative-QTOFsplash10-0171-2120061950-c114e5cb2af8c6ea5b242015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heme O 40V, Negative-QTOFsplash10-00fs-0000090410-19e8eef5041c9549ea3f2015-09-15Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heme O 10V, Negative-QTOFsplash10-000i-0000000090-46c44cfe9d493547a9192021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heme O 20V, Negative-QTOFsplash10-00ri-0100002790-aa7b2dbeb177907521b72021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heme O 40V, Negative-QTOFsplash10-00g0-0000024930-47277d8050776dbaab1c2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heme O 10V, Positive-QTOFsplash10-0079-2000001690-d482b755c66f4c96c8d02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heme O 20V, Positive-QTOFsplash10-003s-6200006910-8a7a86584f45027cc9392021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Heme O 40V, Positive-QTOFsplash10-067j-8400009320-337b466a95de04a44a142021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022457
KNApSAcK IDNot Available
Chemspider ID3571849
KEGG Compound IDC15672
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHeme O
METLIN ID6044
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID24480
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in protoheme IX farnesyltransferase activity
Specific function:
Converts protoheme IX and farnesyl diphosphate to heme O (By similarity).
Gene Name:
COX10
Uniprot ID:
Q12887
Molecular weight:
Not Available
Reactions
Heme + Water + Farnesyl pyrophosphate → Heme O + Pyrophosphatedetails
General function:
Involved in protein complex assembly
Specific function:
May be involved in the biosynthesis of heme A.
Gene Name:
COX15
Uniprot ID:
Q7KZN9
Molecular weight:
Not Available
Reactions
Heme O → Heme Adetails