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Human Metabolome Database Version 2.5

 

Showing metabocard for Heme A (HMDB06901)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2008-08-15 15:23:06
Update Date 2009-05-05 21:01:17
Accession Number HMDB06901
Secondary Accession Numbers HMDB06967
Common Name Heme A
Description Heme 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chain at ring position 8 is oxidized into a formyl group, and one of the vinyl side chains, at ring position 2, has been replaced by an isoprenoid chain.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)
Synonyms
  1. [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-)
  2. (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-)
  3. Heme a
Chemical IUPAC Name Heme A
Chemical Formula C49H56FeN4O6
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Heterocyclic molecules
Class
  • Porphyrins
Sub Class
  • Miscellaneous porphyrins
Family
  • Mammalian Metabolite
Species
  • cation
  • aldehyde
  • secondary alcohol
  • quaternary ammonium salt
  • carboxylic acid
  • alkene
  • aromatic compound
  • heterocyclic compound
Biofunction
  • Oxygen transport, Redox control
Application
—
Source
  • Endogenous
Average Molecular Weight 852.837
Monoisotopic Molecular Weight 852.354919
Isomeric SMILES CC(C)=CCCC(C)=CCCC(C)=CCCC(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
Canonical SMILES CC(C)=CCCC(C)=CCCC(C)=CCCC(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
KEGG Compound ID C15670 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06901 Link Image
Metagene Link HMDB06901 Link Image
METLIN ID Not Available
PubChem Compound 23724533 Link Image
PubChem Substance 47204997 Link Image
ChEBI ID Not Available
CAS Registry Number 57560-10-8
InChI Identifier InChI=1/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-
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 1.77e-04 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 2.80 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Porphyrin Metabolism SMP00024 Link Image map00860 Link Image
General References Not Available