Human Metabolome Database Version 3.5

Showing metabocard for Heme (HMDB03178)

Record Information
Version 3.5
Creation Date 2006-05-22 09:12:38 -0600
Update Date 2013-02-08 11:22:55 -0700
HMDB ID HMDB03178
Secondary Accession Numbers None
Metabolite Identification
Common Name Heme
Description Heme 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C34H32FeN4O4
Average Molecular Weight 616.487
Monoisotopic Molecular Weight 616.177297665
IUPAC Name 10,14-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 Name 10,14-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 Number 14875-96-8
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 Key YHLKGEDAGPGZPN-RGGAHWMASA-L
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Tetrapyrroles and Derivatives
Sub Class Metallotetrapyrroles
Other Descriptors
  • Organic Compounds
  • Porphyrins
Substituents
  • Carboxylic Acid
  • Dicarboxylic Acid Derivative
  • Organic Transition Metal Moeity
  • Organometallic Compound
  • Pyrrole
  • Quaternary Ammonium Salt
Direct Parent Metalloporphyrins
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Porphyrin and chlorophyll metabolism
  • Enzyme co-factor
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 2.00 ALOGPS
LogS -5.75 ALOGPS
Hydrogen Acceptor Count 0 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 121.19 A2 ChemAxon
Rotatable Bond Count 8 ChemAxon
Refractivity 176.19 ChemAxon
Polarizability 70.03 ChemAxon
Formal Charge 2 ChemAxon
Physiological Charge 2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
Biofluid Locations Not Available
Tissue Location
  • Skin
Pathways
Name SMPDB Link KEGG Link
Porphyrin Metabolism SMP00024 map00860 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB016272
KNApSAcK ID Not Available
Chemspider ID 24604415 Link_out
KEGG Compound ID C00032 Link_out
BioCyc ID HEME_A Link_out
BiGG ID 33586 Link_out
Wikipedia Link Heme Link_out
NuGOwiki Link HMDB03178 Link_out
Metagene Link HMDB03178 Link_out
METLIN ID 3680 Link_out
PubChem Compound Not Available
PDB ID Not Available
ChEBI ID 17627 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  3. Walczyk T, von Blanckenburg F: Natural iron isotope variations in human blood. Science. 2002 Mar 15;295(5562):2065-6. Pubmed: 11896276 Link_out
  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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes

Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 169 enzymes in total.

Name: 5-aminolevulinate synthase, erythroid-specific, mitochondrial
Reactions: Not Available
Gene Name: ALAS2
Uniprot ID: P22557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 5-aminolevulinate synthase, nonspecific, mitochondrial
Reactions: Not Available
Gene Name: ALAS1
Uniprot ID: P13196 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Succinate dehydrogenase cytochrome b560 subunit, mitochondrial
Reactions: Not Available
Gene Name: SDHC
Uniprot ID: Q99643 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde oxidase
Reactions: Not Available
Gene Name: AOX1
Uniprot ID: Q06278 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Heme oxygenase 2
Reactions:
Heme + AH(2) + Oxygen unknown Biliverdin + Fe2+ + CO + A + Water details
Gene Name: HMOX2
Uniprot ID: P30519 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Succinate dehydrogenase [ubiquinone] cytochrome b small subunit, mitochondrial
Reactions: Not Available
Gene Name: SDHD
Uniprot ID: O14521 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: NADPH--cytochrome P450 reductase
Reactions: Not Available
Gene Name: POR
Uniprot ID: P16435 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Heme oxygenase 1
Reactions:
Heme + AH(2) + Oxygen unknown Biliverdin + Fe2+ + CO + A + Water details
Gene Name: HMOX1
Uniprot ID: P09601 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uroporphyrinogen decarboxylase
Reactions: Not Available
Gene Name: UROD
Uniprot ID: P06132 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Coproporphyrinogen-III oxidase, mitochondrial
Reactions: Not Available
Gene Name: CPOX
Uniprot ID: P36551 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lanosterol 14-alpha demethylase
Reactions: Not Available
Gene Name: CYP51A1
Uniprot ID: Q16850 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Thyroid peroxidase
Reactions: Not Available
Gene Name: TPO
Uniprot ID: P07202 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lactoperoxidase
Reactions: Not Available
Gene Name: LPO
Uniprot ID: P22079 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Myeloperoxidase
Reactions: Not Available
Gene Name: MPO
Uniprot ID: P05164 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Eosinophil peroxidase
Reactions: Not Available
Gene Name: EPX
Uniprot ID: P11678 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Uroporphyrinogen-III synthase
Reactions: Not Available
Gene Name: UROS
Uniprot ID: P10746 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Porphobilinogen deaminase
Reactions: Not Available
Gene Name: HMBS
Uniprot ID: P08397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4A11
Reactions: Not Available
Gene Name: CYP4A11
Uniprot ID: Q02928 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Indoleamine 2,3-dioxygenase 1
Reactions: Not Available
Gene Name: IDO1
Uniprot ID: P14902 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 11B1, mitochondrial
Reactions: Not Available
Gene Name: CYP11B1
Uniprot ID: P15538 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cholesterol 7-alpha-monooxygenase
Reactions: Not Available
Gene Name: CYP7A1
Uniprot ID: P22680 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Biliverdin reductase A
Reactions: Not Available
Gene Name: BLVRA
Uniprot ID: P53004 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Flavin reductase (NADPH)
Reactions: Not Available
Gene Name: BLVRB
Uniprot ID: P30043 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cholesterol side-chain cleavage enzyme, mitochondrial
Reactions: Not Available
Gene Name: CYP11A1
Uniprot ID: P05108 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cystathionine beta-synthase
Reactions: Not Available
Gene Name: CBS
Uniprot ID: P35520 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nitric oxide synthase, inducible
Reactions: Not Available
Gene Name: NOS2
Uniprot ID: P35228 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nitric oxide synthase, brain
Reactions: Not Available
Gene Name: NOS1
Uniprot ID: P29475 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Nitric oxide synthase, endothelial
Reactions: Not Available
Gene Name: NOS3
Uniprot ID: P29474 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Succinyl-CoA ligase [ADP-forming] subunit beta, mitochondrial
Reactions: Not Available
Gene Name: SUCLA2
Uniprot ID: Q9P2R7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Prostaglandin G/H synthase 2
Reactions: Not Available
Gene Name: PTGS2
Uniprot ID: P35354 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Prostaglandin G/H synthase 1
Reactions: Not Available
Gene Name: PTGS1
Uniprot ID: P23219 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome b-c1 complex subunit 9
Reactions: Not Available
Gene Name: UQCR10
Uniprot ID: Q9UDW1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome b
Reactions: Not Available
Gene Name: MT-CYB
Uniprot ID: P00156 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome c1, heme protein, mitochondrial
Reactions: Not Available
Gene Name: CYC1
Uniprot ID: P08574 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome b-c1 complex subunit 6, mitochondrial
Reactions: Not Available
Gene Name: UQCRH
Uniprot ID: P07919 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Leukotriene-B(4) omega-hydroxylase 1
Reactions: Not Available
Gene Name: CYP4F2
Uniprot ID: P78329 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Leukotriene-B(4) omega-hydroxylase 2
Reactions: Not Available
Gene Name: CYP4F3
Uniprot ID: Q08477 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protoporphyrinogen oxidase
Reactions: Not Available
Gene Name: PPOX
Uniprot ID: P50336 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C9
Reactions: Not Available
Gene Name: CYP2C9
Uniprot ID: P11712 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sterol 26-hydroxylase, mitochondrial
Reactions: Not Available
Gene Name: CYP27A1
Uniprot ID: Q02318 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions: Not Available
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial
Reactions: Not Available
Gene Name: CYP27B1
Uniprot ID: O15528 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Steroid 17-alpha-hydroxylase/17,20 lyase
Reactions: Not Available
Gene Name: CYP17A1
Uniprot ID: P05093 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Sulfite oxidase, mitochondrial
Reactions: Not Available
Gene Name: SUOX
Uniprot ID: P51687 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ferrochelatase, mitochondrial
Reactions:
Heme + Hydrogen Ion unknown Protoporphyrin IX + Fe2+ details
Protoporphyrin IX + Fe2+ unknown Heme + Hydrogen Ion details
Gene Name: FECH
Uniprot ID: P22830 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Delta-aminolevulinic acid dehydratase
Reactions: Not Available
Gene Name: ALAD
Uniprot ID: P13716 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Guanylate cyclase soluble subunit beta-1
Reactions: Not Available
Gene Name: GUCY1B3
Uniprot ID: Q02153 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Guanylate cyclase soluble subunit beta-2
Reactions: Not Available
Gene Name: GUCY1B2
Uniprot ID: O75343 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Prostacyclin synthase
Reactions: Not Available
Gene Name: PTGIS
Uniprot ID: Q16647 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Transporters
Name: Proton-coupled folate transporter
Reactions: Not Available
Gene Name: SLC46A1
Uniprot ID: Q96NT5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA