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13422-55-4 | Methylcobalamin
CAS No: 13422-55-4 Catalog No: AG003S3I MDL No:MFCD00082483
Product Description
Catalog Number:
AG003S3I
Chemical Name:
Methylcobalamin
CAS Number:
13422-55-4
Molecular Formula:
C64H93CoN13O13P++++
Molecular Weight:
1342.4095
MDL Number:
MFCD00082483
IUPAC Name:
carbanide;cobalt(3+);[(2R,3S,4R,5S)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] 1-[3-[(1R,2R,3R,5Z,7S,10Z,12S,13S,15Z,17S,18S,19R)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7,12,17-tetrahydro-1H-corrin-24-id-3-yl]propanoylamino]propan-2-yl phosphate
InChI:
InChI=1S/C62H90N13O14P.CH3.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);1H3;/q;-1;+3/p-2/t31?,34-,35-,36-,37+,41-,52-,53-,56-,57+,59-,60+,61+,62+;;/m1../s1
InChI Key:
ZFLASALABLFSNM-WYVZQNDMSA-L
SMILES:
OCC1OC2C(C1OP(=C)([O-])OC(C)CNC(=O)CCC1(C3=C(C4=[N+]5[Co+]67([n+]8cn2c2cc(C)c(cc82)C)(C)[N+]2=C(C=C5C(C4CCC(=O)N)(C)C)C(C(C2=C(C2=[N+]7C(C(N36)C1CC(=O)N)(C)C(C2CCC(=O)N)(C)CC(=O)N)C)(C)CC(=O)N)CCC(=O)N)C)C)O
EC Number:
236-535-3
Properties
Complexity:
3150
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
3
Defined Atom Stereocenter Count:
13
Defined Bond Stereocenter Count:
3
Exact Mass:
1343.588g/mol
Formal Charge:
0
Heavy Atom Count:
92
Hydrogen Bond Acceptor Count:
20
Hydrogen Bond Donor Count:
9
Isotope Atom Count:
0
Molecular Weight:
1344.405g/mol
Monoisotopic Mass:
1343.588g/mol
Rotatable Bond Count:
26
Topological Polar Surface Area:
452A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
Literature
| Title | Journal |
|---|---|
| Ultrafast infrared spectral fingerprints of vitamin B12 and related cobalamins. | The journal of physical chemistry. A 20120614 |
| Corrin ring-induced redox tuning. | Chemical communications (Cambridge, England) 20120511 |
| Advanced glycation end-products inhibition improves endothelial dysfunction in rheumatoid arthritis. | International journal of rheumatic diseases 20120201 |
| Leukoencephalopathies associated with disorders of cobalamin and folate metabolism. | Seminars in neurology 20120201 |
| Biochemistry of B12-cofactors in human metabolism. | Sub-cellular biochemistry 20120101 |
| Case of Ramsay-Hunt syndrome associated with dysphagia. | The Journal of dermatology 20111201 |
| Oral vitamin B12 replacement: an effective treatment for vitamin B12 deficiency after total gastrectomy in gastric cancer patients. | Annals of surgical oncology 20111201 |
| In vitro phosphinate methylation by PhpK from Kitasatospora phosalacinea. | Biochemistry 20111025 |
| Cortical blindness caused by hypoxemia following an asthma attack. | Japanese journal of ophthalmology 20110901 |
| [Clinical observation on diabetic peripheral neuropathy treated with electroacupuncture and acupoint injection]. | Zhongguo zhen jiu = Chinese acupuncture & moxibustion 20110701 |
| A randomized placebo controlled trial of homocysteine lowering to reduce cognitive decline in older demented people. | Clinical nutrition (Edinburgh, Scotland) 20110601 |
| Electronic structure of cofactor-substrate reactant complex involved in the methyl transfer reaction catalyzed by cobalamin-dependent methionine synthase. | The journal of physical chemistry. B 20110526 |
| Akt/mammalian target of rapamycin signaling pathway regulates neurite outgrowth in cerebellar granule neurons stimulated by methylcobalamin. | Neuroscience letters 20110520 |
| Methylcobalamin effects on diabetic neuropathy and nerve protein kinase C in rats. | European journal of clinical investigation 20110401 |
| Methyl Vitamin B12 but not methylfolate rescues a motor neuron-like cell line from homocysteine-mediated cell death. | Toxicology and applied pharmacology 20110315 |
| Inborn errors of cobalamin absorption and metabolism. | American journal of medical genetics. Part C, Seminars in medical genetics 20110215 |
| Methylcobalamin, but not methylprednisolone or pleiotrophin, accelerates the recovery of rat biceps after ulnar to musculocutaneous nerve transfer. | Neuroscience 20101215 |
| Lumbar spinal stenosis: a brief review of the nonsurgical management. | Canadian journal of anaesthesia = Journal canadien d'anesthesie 20100701 |
| Randomized controlled trial of the effect of short-term coadministration of methylcobalamin and folate on serum ADMA concentration in patients receiving long-term hemodialysis. | American journal of kidney diseases : the official journal of the National Kidney Foundation 20100601 |
| Thermolability of mutant MMACHC protein in the vitamin B12-responsive cblC disorder. | Molecular genetics and metabolism 20100501 |
| The preventive efficacy of methylcobalamin on rat peripheral neuropathy influenced by diabetes via neural IGF-1 levels. | Nutritional neuroscience 20100401 |
| L-methylfolate, methylcobalamin, and N-acetylcysteine in the treatment of Alzheimer's disease-related cognitive decline. | CNS spectrums 20100101 |
| Commentary on: L-methylfolate, methylcobolamine, and N-acetylcysteine in the treatment of Alzheimer's disease-related cognitive decline. | CNS spectrums 20100101 |
| Early co-administration of vitamin E acetate and methylcobalamin improves thermal hyperalgesia and motor nerve conduction velocity following sciatic nerve crush injury in rats. | Pharmacological reports : PR 20100101 |
| Improvement of cutaneous sensitivity in diabetic peripheral neuropathy with combination L-methylfolate, methylcobalamin, and pyridoxal 5'-phosphate. | Reviews in neurological diseases 20100101 |
| A human vitamin B12 trafficking protein uses glutathione transferase activity for processing alkylcobalamins. | The Journal of biological chemistry 20091127 |
| High resolution crystal structure of the methylcobalamin analogues ethylcobalamin and butylcobalamin by X-ray synchrotron diffraction. | Inorganic chemistry 20090720 |
| Photodissociation of Co-C bond in methyl- and ethylcobalamin: an insight from TD-DFT calculations. | The journal of physical chemistry. B 20090514 |
| Efficacy of methylcobalamin and folinic acid treatment on glutathione redox status in children with autism. | The American journal of clinical nutrition 20090101 |
| Effects of plasma homocysteine levels on serum HTase/PON activity in patients with type 2 diabetes. | Advances in therapy 20080901 |
| Time-dependent density functional theory study of cobalt corrinoids: Electronically excited states of methylcobalamin. | The Journal of chemical physics 20080828 |
| Treatment options for patients with Bell's palsy. | American family physician 20080801 |
| Treatment options for patients with Bell's palsy. | American family physician 20080801 |
| Mecobalamin. | Expert opinion on investigational drugs 20080601 |
| Causes of and diagnostic approach to methylmalonic acidurias. | Journal of inherited metabolic disease 20080601 |
| Methylcobalamin inhibits fibroblast growth factor-8 stimulated proliferation and induces apoptosis in Shionogi carcinoma cells. | International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition 20080101 |
| Acute-onset pancytopenia in a postpartum lactating woman. | International journal of hematology 20071101 |
| Clonidine, moxonidine, folic acid, and mecobalamin improve baroreflex function in stroke-prone, spontaneously hypertensive rats. | Acta pharmacologica Sinica 20071001 |
| [Clinical trials of ultra-high-dose methylcobalamin in ALS]. | Brain and nerve = Shinkei kenkyu no shinpo 20071001 |
| [Effects of intervention therapy of methylcobalamin and folic acid on plasma homocysteine concentration and homocysteine thiolactonases/paraoxonase activity in patients with type 2 diabetes mellitus]. | Zhonghua yi xue za zhi 20070123 |
| [The ability of bacterial dna methyltransferases to use methylcobalamine as a cofactor in DNA methylation reactions]. | Biomeditsinskaia khimiia 20070101 |
| Inaccurate description of collaborating hospitals in a study of the effect of folate and mecobalamin on hip fractures after stroke. | JAMA 20060726 |
| Hyperhomocysteinemia and functional cobalamin deficiency due to granulocytosis-induced alterations in the cobalamin-binding protein. | Haematologica 20060301 |
| Subacute combined degeneration of the spinal cord concomitant with gastric cancer. | Internal medicine (Tokyo, Japan) 20060101 |
| Development of a method for the separation of corrinoids in ovine tissues by HPLC. | Biomedical chromatography : BMC 20050501 |
| Disturbed visual system function in methionine synthase deficiency. | Graefe's archive for clinical and experimental ophthalmology = Albrecht von Graefes Archiv fur klinische und experimentelle Ophthalmologie 20050501 |
| Methyl transfer reactivity of five-coordinate CH3CoIIIPc. | Inorganic chemistry 20050307 |
| Effect of folate and mecobalamin on hip fractures in patients with stroke: a randomized controlled trial. | JAMA 20050302 |
| Homocysteine and fracture prevention. | JAMA 20050302 |
| A case of relapsing polychondritis preceded by inner ear involvement. | Auris, nasus, larynx 20050301 |
| [Hyperhomocysteinemia as a vascular risk factor in chronic hemodialysis patients]. | Medicina 20050101 |
| Structure-energy relations in methylcobalamin with and without bound axial base. | Inorganic chemistry 20041018 |
| The cblD defect causes either isolated or combined deficiency of methylcobalamin and adenosylcobalamin synthesis. | The Journal of biological chemistry 20041008 |
| The protective role of Mecobalamin following optic nerve crush in adult rats. | Yan ke xue bao = Eye science 20040901 |
| Accurate redetermination of the X-ray structure and electronic bonding in adenosylcobalamin. | Inorganic chemistry 20040223 |
| Determination of vitamin B12 using the enzyme glycerol dehydrase. | Scandinavian journal of clinical and laboratory investigation 20040101 |
| Cobalamin-dependent methionine synthase: probing the role of the axial base in catalysis of methyl transfer between methyltetrahydrofolate and exogenous cob(I)alamin or cob(I)inamide. | Biochemistry 20031216 |
| Neuropsychiatric disturbances in presumed late-onset cobalamin C disease. | Archives of neurology 20031001 |
| [A case of subacute combined degeneration with normal serum vitamin B12 level]. | Rinsho shinkeigaku = Clinical neurology 20030901 |
| Contribution of nitric oxide to the depression of neuronal activity induced by temperature increase in the rat hippocampal CA1 area. | Neuroscience letters 20030703 |
| Spectroscopic and computational studies of Co3+-corrinoids: spectral and electronic properties of the B12 cofactors and biologically relevant precursors. | Journal of the American Chemical Society 20030514 |
| Clinical inquiries. Are drug therapies effective in treating Bell's palsy? | The Journal of family practice 20030201 |
| Hyperhomocysteinemia in Japanese patients with convalescent stage ischemic stroke: effect of combined therapy with folic acid and mecobalamine. | Journal of the neurological sciences 20021015 |
| [Acute neuropathy associated with vitamin B12, B6, and folate deficiency after total gastrectomy]. | Nihon Naika Gakkai zasshi. The Journal of the Japanese Society of Internal Medicine 20020910 |
| Efficacy of methylcobalamin on lowering total homocysteine plasma concentrations in haemodialysis patients receiving high-dose folic acid supplementation. | Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20020501 |
| Randomized trial of methylcobalamin and folate effects on homocysteine in hemodialysis patients. | Nephron 20020501 |
| [Effectiveness of oral vitamin B12 therapy for pernicious anemia and vitamin B12 deficiency anemia]. | [Rinsho ketsueki] The Japanese journal of clinical hematology 20020301 |
| The C677T thermolabile variant of methylene tetrahydrofolate reductase on homocysteine, folate and vitamin B12 in a hemodialysis center. | Medicina 20020101 |
| [Clinical observation of combined therapeutic effect of prostaglandin E1 and mecobalamin on diabetic peripheral neuropathy]. | Hunan yi ke da xue xue bao = Hunan yike daxue xuebao = Bulletin of Hunan Medical University 20010828 |
| Formation and emission of volatile polonium compound by microbial activity and polonium methylation with methylcobalamin. | Environmental science & technology 20010715 |
| Homocysteine metabolism in children with Down syndrome: in vitro modulation. | American journal of human genetics 20010701 |
| Characterization of a three-component vanillate O-demethylase from Moorella thermoacetica. | Journal of bacteriology 20010601 |
| Quantitation of rate enhancements attained by the binding of cobalamin to methionine synthase. | Biochemistry 20010424 |
| Cobalamin (Cbl) C/D deficiency: clinical, neurophysiological and neuroradiologic findings in 14 cases. | Neuropediatrics 20010201 |
| Induction of apoptosis in an androgen-dependent mouse mammary carcinoma cell line by methylcobalamin. | Anticancer research 20010101 |
| Intrinsic factors involved in the depression of neuronal activity induced by temperature increase in rat hippocampal neurons. | The Kurume medical journal 20010101 |
| Cobalamin inhibition of HIV-1 integrase and integration of HIV-1 DNA into cellular DNA. | Biochemical and biophysical research communications 19980519 |
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