Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-08-12 20:37:00 UTC |
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Update Date | 2021-09-14 15:17:03 UTC |
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HMDB ID | HMDB0003429 |
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Secondary Accession Numbers | - HMDB0006470
- HMDB03429
- HMDB06470
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Metabolite Identification |
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Common Name | Cob(I)alamin |
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Description | Cob(I)alamin is the substrate of the enzyme ATP:cob(I)alamin adenosyltransferase (EC 2.5.1.17), that converts reduced cob(I)alamin to the adenosylcobalamin co-factor required for the functional activity of methylmalonyl-CoA mutase (EC 5.4.99.2). Mutations in the human MMAB gene result in a block in adenosylcobalamin synthesis and are responsible for the cblB complementation group of inherited vitamin B12 disorders, such as cobalamin malabsorption, which is an inborn error of metabolism. Vitamin B12 (cobalamin) is a complex cobalt-containing molecule that is essential to human health. It is synthesized in bacteria where it catalyzes numerous methyl transfer and intramolecular rearrangement reactions. In mammals, it is the co-factor of only two enzymes: methionine synthase, which catalyzes the transfer of a methyl group from methyltetrahydrofolate to homocysteine to form methionine, and methylmalonyl-CoA mutase, which catalyzes the rearrangement of methylmalonyl-CoA to form succinyl-CoA. For both enzymes, the vitamin must be modified through intracellular metabolism to co-factor forms: methylcobalamin (MeCbl)1 for methionine synthase and adenosylcobalamin (AdoCbl) for methylmalonyl-CoA mutase (PMID: 16439175 ). |
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Structure | [H][C@]12[C@H](CC(N)=O)[C@@]3(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@@H]4[C@@H](CO)O[C@@H]([C@@H]4O)N4C=[N+](C5=CC(C)=C(C)C=C45)[Co-4]456N1C3=C(C)C1=[N+]4C(=CC3=[N+]5C(=C(C)C4=[N+]6[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)C(C)(C)[C@@H]1CCC(N)=O InChI=1S/C62H90N13O14P.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);/q;+1/p-1/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;/m1./s1 |
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Synonyms | Value | Source |
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Vitamin b-12S | ChEBI | Vitamin b12S | ChEBI | Cyanocobalamin | HMDB | Hydrido-cobalamin | HMDB | Hydridocobalamin | HMDB |
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Chemical Formula | C62H89CoN13O14P |
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Average Molecular Weight | 1330.378 |
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Monoisotopic Molecular Weight | 1329.572151 |
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IUPAC Name | (10S,12R,13S,17R,23R,24R,25R,30S,35S,36S,40S,41S,42R,46R)-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-15,46-dihydroxy-12-(hydroxymethyl)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-15,20-dioxo-11,14,16-trioxa-2lambda5,9,19,26,43lambda5,44lambda5,45lambda5-heptaaza-15lambda5-phospha-1-cobaltadodecacyclo[27.14.1.1^{1,34}.1^{2,9}.1^{10,13}.0^{1,26}.0^{3,8}.0^{23,27}.0^{25,42}.0^{32,44}.0^{39,43}.0^{37,45}]heptatetraconta-2(47),3,5,7,27,29(44),32,34(45),37,39(43)-decaene-2,43,44,45-tetrakis(ylium)-1,1,1,1-tetrauide |
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Traditional Name | (10S,12R,13S,17R,23R,24R,25R,30S,35S,36S,40S,41S,42R,46R)-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-15,46-dihydroxy-12-(hydroxymethyl)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-15,20-dioxo-11,14,16-trioxa-2lambda5,9,19,26,43lambda5,44lambda5,45lambda5-heptaaza-15lambda5-phospha-1-cobaltadodecacyclo[27.14.1.1^{1,34}.1^{2,9}.1^{10,13}.0^{1,26}.0^{3,8}.0^{23,27}.0^{25,42}.0^{32,44}.0^{39,43}.0^{37,45}]heptatetraconta-2(47),3,5,7,27,29(44),32,34(45),37,39(43)-decaene-2,43,44,45-tetrakis(ylium)-1,1,1,1-tetrauide |
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CAS Registry Number | 18534-66-2 |
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SMILES | [H][C@]12[C@H](CC(N)=O)[C@@]3(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@@H]4[C@@H](CO)O[C@@H]([C@@H]4O)N4C=[N+](C5=CC(C)=C(C)C=C45)[Co-4]456N1C3=C(C)C1=[N+]4C(=CC3=[N+]5C(=C(C)C4=[N+]6[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]3CCC(N)=O)C(C)(C)[C@@H]1CCC(N)=O |
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InChI Identifier | InChI=1S/C62H90N13O14P.Co/c1-29-20-39-40(21-30(29)2)75(28-70-39)57-52(84)53(41(27-76)87-57)89-90(85,86)88-31(3)26-69-49(83)18-19-59(8)37(22-46(66)80)56-62(11)61(10,25-48(68)82)36(14-17-45(65)79)51(74-62)33(5)55-60(9,24-47(67)81)34(12-15-43(63)77)38(71-55)23-42-58(6,7)35(13-16-44(64)78)50(72-42)32(4)54(59)73-56;/h20-21,23,28,31,34-37,41,52-53,56-57,76,84H,12-19,22,24-27H2,1-11H3,(H15,63,64,65,66,67,68,69,71,72,73,74,77,78,79,80,81,82,83,85,86);/q;+1/p-1/t31-,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;/m1./s1 |
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InChI Key | OMAOKVYASDIYQG-DSRCUDDDSA-M |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cobalamin derivatives. These are organic compounds containing a corrin ring, a cobalt atom, an a nucleotide moiety. Cobalamin Derivatives are actually derived from vitamin B12. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Tetrapyrroles and derivatives |
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Sub Class | Corrinoids |
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Direct Parent | Cobalamin derivatives |
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Alternative Parents | |
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Substituents | - Cobalamin
- Metallotetrapyrrole skeleton
- 1-ribofuranosylbenzimidazole
- Pentose phosphate
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Pentose monosaccharide
- Benzimidazole
- Dialkyl phosphate
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Benzenoid
- Azole
- Imidazole
- Heteroaromatic compound
- Pyrrolidine
- Pyrroline
- Tetrahydrofuran
- Secondary alcohol
- Ketimine
- Propargyl-type 1,3-dipolar organic compound
- Carboximidic acid
- Secondary amine
- Carboximidic acid derivative
- Secondary aliphatic amine
- Enamine
- Oxacycle
- Azacycle
- Organic transition metal salt
- Organic 1,3-dipolar compound
- Primary alcohol
- Imine
- Amine
- Organic oxide
- Organopnictogen compound
- Hydrocarbon derivative
- Organic zwitterion
- Organic oxygen compound
- Alcohol
- Organonitrogen compound
- Organooxygen compound
- Organic cobalt salt
- Organic salt
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Kovats Retention IndicesNot Available |
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Spectra |
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| MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cob(I)alamin 10V, Positive-QTOF | splash10-01q0-0097000000-0021927d06a72e6704c3 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cob(I)alamin 20V, Positive-QTOF | splash10-03xu-0093000000-2a92353bd428991e480f | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cob(I)alamin 40V, Positive-QTOF | splash10-0007-0090000000-93430347c6ecec5d8cd3 | 2019-02-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cob(I)alamin 10V, Negative-QTOF | splash10-01ti-0089000000-f49f5ec60e91e3af0114 | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cob(I)alamin 20V, Negative-QTOF | splash10-01ox-1094000000-2defa0906339d10ef64d | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cob(I)alamin 40V, Negative-QTOF | splash10-0006-8092000000-345ba89e7a43d9592f0f | 2019-02-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cob(I)alamin 10V, Positive-QTOF | splash10-03e9-0029000000-5ba3ede307aec5f3cdc0 | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cob(I)alamin 20V, Positive-QTOF | splash10-0il0-0094000000-04ee85a1354b2737544e | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cob(I)alamin 40V, Positive-QTOF | splash10-0fa2-2292000000-b181211315ceb5efcd5e | 2021-09-21 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cob(I)alamin 10V, Negative-QTOF | splash10-004i-0009000000-35bd64cbc837fba1aaff | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cob(I)alamin 20V, Negative-QTOF | splash10-056r-2079000000-000e2e52473ee1bde9e5 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Cob(I)alamin 40V, Negative-QTOF | splash10-00o0-0094000000-66f0381254255a3b7333 | 2021-09-25 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | Not Available |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 0.0003 (0.00016-0.0005) uM | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 0.000150-0.000400 uM | Adult (>18 years old) | Not Specified | Normal | | details | Blood | Detected and Quantified | 0.000407 (0.000336-0.000540) uM | Children (1 - 13 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 0.00041 (0.00015-0.00067) uM | Adult (>18 years old) | Both | Cobalamin malabsorption | | details | Blood | Detected and Quantified | 0.000094 (0.000037-0.00015) uM | Children (1-13 years old) | Both | Cobalamin malabsorption | | details | Blood | Detected and Quantified | 0.000222 uM | Adult (>18 years old) | Male | Dimethylglycinuria | | details |
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Associated Disorders and Diseases |
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Disease References | Cobalamin malabsorption |
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- G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
| Dimethylglycine Dehydrogenase Deficiency |
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- Moolenaar SH, Poggi-Bach J, Engelke UF, Corstiaensen JM, Heerschap A, de Jong JG, Binzak BA, Vockley J, Wevers RA: Defect in dimethylglycine dehydrogenase, a new inborn error of metabolism: NMR spectroscopy study. Clin Chem. 1999 Apr;45(4):459-64. [PubMed:10102904 ]
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Associated OMIM IDs | - 605850 (Dimethylglycine Dehydrogenase Deficiency)
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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 | FDB021826 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 21864800 |
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KEGG Compound ID | C00853 |
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BioCyc ID | Not Available |
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BiGG ID | 36205 |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 53477772 |
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PDB ID | Not Available |
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ChEBI ID | 15982 |
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Food Biomarker Ontology | Not Available |
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VMH ID | CBL1 |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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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 | - Zhang J, Dobson CM, Wu X, Lerner-Ellis J, Rosenblatt DS, Gravel RA: Impact of cblB mutations on the function of ATP:cob(I)alamin adenosyltransferase in disorders of vitamin B12 metabolism. Mol Genet Metab. 2006 Apr;87(4):315-22. Epub 2006 Jan 24. [PubMed:16439175 ]
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