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Record Information
Version3.6
Creation Date2008-08-15 14:23:06 UTC
Update Date2016-02-11 01:08:07 UTC
HMDB IDHMDB06901
Secondary Accession Numbers
  • HMDB06967
Metabolite Identification
Common NameHeme A
DescriptionHeme A differs from heme B in that a methyl side chain at ring position 8 is oxidized into a formyl group, and one of the vinyl side chains, at ring position 2, has been replaced by an isoprenoid chain. Like heme B, heme A is often attached to the apoprotein (cytochromes or globins) through a coordination bond between the heme iron and a conserved amino acid side-chain. An example of a metalloprotein that contains heme A is cytochrome c oxidase. Both the formyl group and the isoprenoid side chain are thought to play important roles in conservation of the energy of oxygen reduction by cytochrome c oxidase.(Wikipedia).
Structure
Thumb
Synonyms
ValueSource
(SP-4-2)[7-Ethenyl-17-formyl-12-[(4E,8E)-1-hydroxy-5,9,13-trimethyl-4,8,12-tetradecatrienyl]-3,8,13-trimethyl-21H,23H-porphine-2,18-dipropanoato(4-)-kappan21,kappan22,kappan23,kappan24]-ferrate(2-)HMDB
[SP-4-2-(e,e)]-[7-Ethenyl-17-formyl-12-(1-hydroxy-5,9,13-trimethyl-4,8,12-tetradecatrienyl)-3,8,13-trimethyl-21H,23H-porphine-2,18-dipropanoato(4-)-N21,N22,N23,N24]-ferrate(2-)HMDB
Chemical FormulaC49H56FeN4O6
Average Molecular Weight852.837
Monoisotopic Molecular Weight852.354927677
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number57560-10-8
SMILES
CC(C)=CCC\C(C)=C\CC\C(C)=C\CCC(O)C1=C2C=C3C(C)=C(C=C)C4=[N]3[Fe++]35N6C(=C4)C(C)=C(CCC(O)=O)C6=CC4=[N]3C(=CC(N25)=C1C)C(C=O)=C4CCC(O)=O
InChI Identifier
InChI=1S/C49H58N4O6.Fe/c1-9-34-31(6)39-25-45-49(46(55)18-12-17-30(5)16-11-15-29(4)14-10-13-28(2)3)33(8)40(52-45)24-44-37(27-54)36(20-22-48(58)59)43(53-44)26-42-35(19-21-47(56)57)32(7)38(51-42)23-41(34)50-39;/h9,13,15,17,23-27,46,55H,1,10-12,14,16,18-22H2,2-8H3,(H4,50,51,52,53,54,56,57,58,59);/q;+4/p-2/b29-15+,30-17+,38-23-,39-25-,40-24-,41-23-,42-26-,43-26-,44-24-,45-25-;
InChI KeyInChIKey=RRJCKGQQRUXGQR-ONCSLILDSA-L
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as metalloporphyrins. These are polycyclic compounds containing a porphyrin moiety and a metal atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassMetallotetrapyrroles
Direct ParentMetalloporphyrins
Alternative Parents
Substituents
  • Metalloporphyrin
  • Porphyrin
  • Diterpenoid
  • Aryl-aldehyde
  • Substituted pyrrole
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Pyrrole
  • Secondary alcohol
  • Azacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic transition metal salt
  • Organic salt
  • Aromatic alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Oxygen transport, Redox control
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 Solubility0.000177 mg/mLALOGPS
logP2.8ALOGPS
logS-6.7ALOGPS
Physiological Charge2ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area158.49 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity249.86 m3·mol-1ChemAxon
Polarizability99.4 Å3ChemAxon
Number of Rings8ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Acute Intermittent PorphyriaSMP00344Not Available
Congenital Erythropoietic Porphyria (CEP) or Gunther DiseaseSMP00345Not Available
Hereditary Coproporphyria (HCP)SMP00342Not Available
Porphyria Variegata (PV)SMP00346Not Available
Porphyrin MetabolismSMP00024map00860
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 IDFDB024148
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15670
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06901
Metagene LinkHMDB06901
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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