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| Record Information |
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| Version | 4.0 |
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| Status | Detected but not Quantified |
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| Creation Date | 2006-05-22 15:12:38 UTC |
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| Update Date | 2020-04-22 23:33:23 UTC |
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| HMDB ID | HMDB0003178 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Heme |
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| Description | Heme is also known as protoheme or [fe(ppix)]. Not all porphyrins contain iron, but a substantial fraction of porphyrin-containing metalloproteins have heme as their prosthetic subunit; these are known as hemoproteins. Heme is a weakly acidic compound (based on its pKa). Heme exists in all living organisms, ranging from bacteria to humans. In humans, heme is involved in ibuprofen action pathway. Outside of the human body, Heme has been detected, but not quantified in, several different foods, such as tarragons, carobs, wild leeks, breadfruits, and black chokeberries. This could make heme a potential biomarker for the consumption of these foods. It is found free in tissues and as the prosthetic group in many hemeproteins. A heme or Heme is a prosthetic group that consists of an iron atom contained in the center of a large heterocyclic organic ring called a porphyrin. Heme is the color-furnishing portion of hemoglobin. |
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| Structure | |
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| Synonyms | | Value | Source |
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| [3,7,12,17-Tetramethyl-8,13-divinylporphyrin-2,18-dipropanoato(2-)]iron(II) | ChEBI | | [Fe(ppix)] | ChEBI | | Fe(ppix) | ChEBI | | Ferroprotoheme | ChEBI | | Ferroprotoporphyrin IX | ChEBI | | Ferrous protoheme | ChEBI | | Ferrous protoheme IX | ChEBI | | Haem | ChEBI | | Iron(II) protoporphyrin IX | ChEBI | | Protoferroheme | ChEBI | | Protoheme | ChEBI | | Heme b | Kegg | | Protoheme IX | Kegg | | Heme | ChEBI |
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| Chemical Formula | C34H32FeN4O4 |
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| Average Molecular Weight | 616.487 |
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| Monoisotopic Molecular Weight | 616.177297665 |
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| IUPAC Name | 4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-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)-1,1-diuide |
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| Traditional Name | 4,20-bis(2-carboxyethyl)-10,15-diethenyl-5,9,14,19-tetramethyl-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)-1,1-diuide |
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| CAS Registry Number | 14875-96-8 |
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| SMILES | CC1=C(CCC(O)=O)C2=CC3=[N+]4C(=CC5=C(C)C(C=C)=C6C=C7C(C)=C(C=C)C8=[N+]7[Fe--]4(N2C1=C8)N56)C(C)=C3CCC(O)=O |
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| 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;+2/p-2/b25-13-,26-13-,27-14-,28-15-,29-14-,30-15-,31-16-,32-16-; |
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| InChI Key | KABFMIBPWCXCRK-RGGAHWMASA-L |
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| Chemical Taxonomy |
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| Classification | Not classified |
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| Ontology |
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| Disposition | Route of exposure: Source: Biological location: |
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| Process | Naturally occurring process: |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| | Spectrum Type | Description | Splash Key | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | Not Available | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | Not Available | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-066r-0000095000-501c4a776d38d61ab89a | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0gi4-0000092000-64c21d0a0f8daa069fb9 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03gs-4000590000-15136ce22e51bdc57377 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0000049000-69ee302652cebc40f13b | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00r2-1000091000-d178bb83079a203a48dc | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-1000090000-f6e437751fbc08f12d1f | Spectrum |
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| Biological Properties |
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| Cellular Locations | - Cytoplasm
- Extracellular
- Mitochondria
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| Biospecimen Locations | |
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| Tissue Locations | |
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| Pathways | |
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| Normal Concentrations |
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| Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details | | Saliva | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Male | Normal | | details |
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| Abnormal Concentrations |
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| Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details |
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| Associated Disorders and Diseases |
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| Disease References | | Colorectal cancer |
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- Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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| Associated OMIM IDs | |
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| External Links |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB031136 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | Not Available |
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| KEGG Compound ID | C00032 |
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| BioCyc ID | Not Available |
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| BiGG ID | Not Available |
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| Wikipedia Link | Heme |
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| METLIN ID | Not Available |
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| PubChem Compound | Not Available |
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| PDB ID | Not Available |
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| ChEBI ID | 17627 |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | PHEME |
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| MarkerDB ID | |
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| References |
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| Synthesis Reference | Not Available |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - 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 ]
- 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 ]
- Walczyk T, von Blanckenburg F: Natural iron isotope variations in human blood. Science. 2002 Mar 15;295(5562):2065-6. [PubMed:11896276 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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