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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-15 14:23:06 UTC
Update Date2021-09-14 14:59:35 UTC
HMDB IDHMDB0006901
Secondary Accession Numbers
  • HMDB0006967
  • HMDB06901
  • 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chain at ring position 8 is oxidized into a formyl group, and one of the vinyl side chains, at ring position 2, has been replaced by an isoprenoid chain.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
Data?1582752414
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 Name4,20-bis(2-carboxyethyl)-15-ethenyl-5-formyl-10-[(4E,8E)-1-hydroxy-5,9,13-trimethyltetradeca-4,8,12-trien-1-yl]-9,14,19-trimethyl-2lambda5,22,23lambda5,25-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-2,23-bis(ylium)
Traditional Name4,20-bis(2-carboxyethyl)-15-ethenyl-5-formyl-10-[(4E,8E)-1-hydroxy-5,9,13-trimethyltetradeca-4,8,12-trien-1-yl]-9,14,19-trimethyl-2lambda5,22,23lambda5,25-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-2,23-bis(ylium)
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 KeyRRJCKGQQRUXGQR-ONCSLILDSA-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 effectNot Available
Disposition
Process
RoleNot Available
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 Solubility0.00018 g/LALOGPS
logP2.16ALOGPS
logP4.58ChemAxon
logS-6.6ALOGPS
pKa (Strongest Acidic)3.2ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area129.52 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity244.19 m³·mol⁻¹ChemAxon
Polarizability100.2 ųChemAxon
Number of Rings8ChemAxon
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]+281.532859911
AllCCS[M+H-H2O]+280.832859911
AllCCS[M+NH4]+282.232859911
AllCCS[M+Na]+282.332859911
AllCCS[M-H]-300.732859911
AllCCS[M+Na-2H]-306.532859911
AllCCS[M+HCOO]-312.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Heme ACC(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)=O9522.3Standard polar33892256
Heme ACC(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)=O4360.9Standard non polar33892256
Heme ACC(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)=O6185.7Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
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 IDFDB024148
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15670
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHeme A
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
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 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