Record Information
Version3.6
Creation Date2006-05-22 15:12:38 UTC
Update Date2013-02-08 18:22:55 UTC
HMDB IDHMDB03178
Secondary Accession NumbersNone
Metabolite Identification
Common NameHeme
DescriptionHeme is the color-furnishing portion of hemoglobin. It is found free in tissues and as the prosthetic group in many hemeproteins. A heme or haem is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins.
Structure
Thumb
Synonyms
  1. (protoporphyrinato)iron
  2. Ferroheme
  3. Ferroheme b
  4. Ferroprotoheme
  5. Ferroprotoporphyrin
  6. Ferroprotoporphyrin IX
  7. Ferrous protoheme
  8. Ferrous protoheme IX
  9. Haem
  10. Hem
  11. Heme
  12. Iron protoporphyrin
  13. Iron protoporphyrin IX
  14. Iron(II) protoporphyrin IX
  15. Protoferroheme
  16. Protohaem
  17. Protoheme
  18. Protoheme IX
  19. Reduced hematin
Chemical FormulaC34H32FeN4O4
Average Molecular Weight616.487
Monoisotopic Molecular Weight616.177297665
IUPAC Name10,14-bis(2-carboxyethyl)-5,20-diethenyl-4,9,15,19-tetramethyl-2$l^{4},22$l^{4},23,25-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-2,4,6,8,10,12,14,16,18(22),19,21(24)-undecaene-1,1-bis(ylium)
Traditional IUPAC Name10,14-bis(2-carboxyethyl)-5,20-diethenyl-4,9,15,19-tetramethyl-2$l^{4},22$l^{4},23,25-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-2,4,6,8,10,12,14,16,18(22),19,21(24)-undecaene-1,1-bis(ylium)
CAS Registry Number14875-96-8
SMILES
CC1=C(CCC(O)=O)C2=CC3=C(CCC(O)=O)C(C)=C4C=C5C(C=C)=C(C)C6=[N]5[Fe++]5(N2C1=CC1=[N]5C(=C6)C(C=C)=C1C)N34
InChI Identifier
InChI=1S/C34H34N4O4.Fe/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25;/h7-8,13-16H,1-2,9-12H2,3-6H3,(H4,35,36,37,38,39,40,41,42);/q;+4/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-;
InChI KeyYHLKGEDAGPGZPN-RGGAHWMASA-L
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassTetrapyrroles and Derivatives
Sub ClassMetallotetrapyrroles
Other Descriptors
  • Organic Compounds
  • Porphyrins
Substituents
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Organic Transition Metal Moeity
  • Organometallic Compound
  • Pyrrole
  • Quaternary Ammonium Salt
Direct ParentMetalloporphyrins
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Porphyrin and chlorophyll metabolism
  • Enzyme co-factor
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
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 solubility0.0012 g/LALOGPS
logP2ALOGPS
logS-5.8ALOGPS
physiological charge2ChemAxon
hydrogen acceptor count0ChemAxon
hydrogen donor count0ChemAxon
polar surface area121.19ChemAxon
rotatable bond count8ChemAxon
refractivity176.19ChemAxon
polarizability70.03ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid LocationsNot Available
Tissue Location
  • Skin
Pathways
NameSMPDB LinkKEGG Link
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 IDFDB016272
KNApSAcK IDNot Available
Chemspider ID24604415
KEGG Compound IDC00032
BioCyc IDHEME_A
BiGG ID33586
Wikipedia LinkHeme
NuGOwiki LinkHMDB03178
Metagene LinkHMDB03178
METLIN ID3680
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17627
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ono F, Sharma BK, Smith CC, Burnett JW, Aurelian L: CD34+ cells in the peripheral blood transport herpes simplex virus DNA fragments to the skin of patients with erythema multiforme (HAEM). J Invest Dermatol. 2005 Jun;124(6):1215-24. Pubmed: 15955097
  2. Allhorn M, Lundqvist K, Schmidtchen A, Akerstrom B: Heme-scavenging role of alpha1-microglobulin in chronic ulcers. J Invest Dermatol. 2003 Sep;121(3):640-6. Pubmed: 12925227
  3. Walczyk T, von Blanckenburg F: Natural iron isotope variations in human blood. Science. 2002 Mar 15;295(5562):2065-6. Pubmed: 11896276
  4. Kuhnel A, Gross U, Doss MO: Hereditary coproporphyria in Germany: clinical-biochemical studies in 53 patients. Clin Biochem. 2000 Aug;33(6):465-73. Pubmed: 11074238
  5. Zhang JP, Normark S: Induction of gene expression in Escherichia coli after pilus-mediated adherence. Science. 1996 Aug 30;273(5279):1234-6. Pubmed: 8703059
  6. Taylor TD, Litt M, Kramer P, Pandolfo M, Angelini L, Nardocci N, Davis S, Pineda M, Hattori H, Flett PJ, Cilio MR, Bertini E, Hayflick SJ: Homozygosity mapping of Hallervorden-Spatz syndrome to chromosome 20p12.3-p13. Nat Genet. 1996 Dec;14(4):479-81. Pubmed: 8944032
  7. Park KK, Park JH, Jung YJ, Chung WY: Inhibitory effects of chlorophyllin, hemin and tetrakis(4-benzoic acid)porphyrin on oxidative DNA damage and mouse skin inflammation induced by 12-O-tetradecanoylphorbol-13-acetate as a possible anti-tumor promoting mechanism. Mutat Res. 2003 Dec 9;542(1-2):89-97. Pubmed: 14644357

Only showing the first 50 proteins. There are 170 proteins in total.

Enzymes

Gene Name:
AOX1
Uniprot ID:
Q06278
Gene Name:
HMOX2
Uniprot ID:
P30519
Reactions
Heme + AH(2) + Oxygen unknown Biliverdin + Fe2+ + CO + A + Waterdetails
Gene Name:
POR
Uniprot ID:
P16435
Gene Name:
HMOX1
Uniprot ID:
P09601
Reactions
Heme + AH(2) + Oxygen unknown Biliverdin + Fe2+ + CO + A + Waterdetails
Gene Name:
UROD
Uniprot ID:
P06132
Gene Name:
CYP51A1
Uniprot ID:
Q16850
Gene Name:
TPO
Uniprot ID:
P07202
Gene Name:
LPO
Uniprot ID:
P22079
Gene Name:
MPO
Uniprot ID:
P05164
Gene Name:
EPX
Uniprot ID:
P11678
Gene Name:
UROS
Uniprot ID:
P10746
Gene Name:
HMBS
Uniprot ID:
P08397
Gene Name:
CYP4A11
Uniprot ID:
Q02928
Gene Name:
IDO1
Uniprot ID:
P14902
Gene Name:
CYP11B1
Uniprot ID:
P15538
Gene Name:
CYP7A1
Uniprot ID:
P22680
Gene Name:
BLVRA
Uniprot ID:
P53004
Gene Name:
BLVRB
Uniprot ID:
P30043
Gene Name:
CBS
Uniprot ID:
P35520
Gene Name:
NOS2
Uniprot ID:
P35228
Gene Name:
NOS1
Uniprot ID:
P29475
Gene Name:
NOS3
Uniprot ID:
P29474
Gene Name:
PTGS2
Uniprot ID:
P35354
Gene Name:
PTGS1
Uniprot ID:
P23219
Gene Name:
UQCR10
Uniprot ID:
Q9UDW1
Gene Name:
MT-CYB
Uniprot ID:
P00156
Gene Name:
CYP4F2
Uniprot ID:
P78329
Gene Name:
CYP4F3
Uniprot ID:
Q08477
Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
PPOX
Uniprot ID:
P50336
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
CYP17A1
Uniprot ID:
P05093
Gene Name:
SUOX
Uniprot ID:
P51687
Gene Name:
FECH
Uniprot ID:
P22830
Reactions
Heme + Hydrogen Ion unknown Protoporphyrin IX + Fe2+details
Protoporphyrin IX + Fe2+ unknown Heme + Hydrogen Iondetails
Gene Name:
GUCY1B3
Uniprot ID:
Q02153
Gene Name:
GUCY1B2
Uniprot ID:
O75343
Gene Name:
PTGIS
Uniprot ID:
Q16647

Transporters

Gene Name:
SLC46A1
Uniprot ID:
Q96NT5

Only showing the first 50 proteins. There are 170 proteins in total.