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MedKoo Cat#: 581263 | Name: Cobamamide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Coenzyme B12 (adenosylcobalamin; AdoCbl) is a biologically active form of vitamin B12 (Item No. 18425). It belongs to the corrinoid group of compounds, which contain a corrin macrocycle, and is produced only by certain bacteria and archaea. It is a cofactor for various enzymes including mutases, eliminases, aminomutases, and a reductase.2 These enzymes catalyze reactions that generate free radicals through release of the adenosyl group, allowing usually unreactive molecules to become reactive. Only one of these enzymes, methylmalonyl CoA mutase, is found in mammals, therefore, the other enzymes must be taken in through the diet. Genetic mutations in enzymes that synthesize AdoCbl lead to AdoCbl deficiency and methylmalonic aciduria.3 Formulations containing AdoCbl are used to treat patients with this disorder.

Chemical Structure

Cobamamide
Cobamamide
CAS#13870-90-1

Theoretical Analysis

MedKoo Cat#: 581263

Name: Cobamamide

CAS#: 13870-90-1

Chemical Formula: C72H100CoN18O17P

Exact Mass: 1578.6583

Molecular Weight: 1579.61

Elemental Analysis: C, 54.75; H, 6.38; Co, 3.73; N, 15.96; O, 17.22; P, 1.96

Price and Availability

Size Price Availability Quantity
50mg USD 350.00 2 Weeks
100mg USD 550.00 2 Weeks
250mg USD 950.00 2 Weeks
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Related CAS #
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Synonym
Cobamamide; Cobamamida; LM 176; LM176; LM176; Calomide; Cobamamida; Coenzyme B12; DMBC; Adenosyl cobalamine; Adenosylcobalamine; AdoCbl; Dibenzcozamide
IUPAC/Chemical Name
co-(5'-deoxyadenosin-5'-yl)-cobinamide, f-(dihydrogen phosphate), inner salt, 3'-ester with (5,6-dimethyl-1-α-D-ribofuranosyl-1H-benzimidazole-κN3)
InChi Key
ZIHHMGTYZOSFRC-YKRUXZDWSA-L
InChi Code
InChI=1S/C62H90N13O14P.C10H12N5O3.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;1-4-6(16)7(17)10(18-4)15-3-14-5-8(11)12-2-13-9(5)15;/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);2-4,6-7,10,16-17H,1H2,(H2,11,12,13);/q;;+2/p-2/t31-,34+,35+,36+,37-,41+,52-,53-,56+,57-,59-,60+,61+,62+;4-,6-,7-,10-;/m00./s1
SMILES Code
NC(CC[C@H]1[C@](CC(N)=O)(C)[C@@]2(C)[C@@H]3[N@@]4/C([C@](C)([C@H]3CC(N)=O)CCC(NC[C@H](C)OP(O[C@@H]5[C@H](O)[C@H](O[C@@H]5CO)N6C=[N](c7cc(C)c(C)cc76)[Co+]4C[C@@H]8O[C@@H]([C@@H](O)[C@H]8O)n9cnc%10c(N)ncnc9%10)([O-])=O)=O)=C(C)/C([C@@H](CCC(N)=O)C/%11(C)C)=NC%11=C\C%12=N/C([C@@](CC(N)=O)(C)[C@@H]%12CCC(N)=O)=C(C)/C1=N2)=O
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,579.61 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Chen JR, Ke SC. Magnetic field effects on coenzyme B(12)- and B(6)-dependent lysine 5,6-aminomutase: switching of the J-resonance through a kinetically competent radical-pair intermediate. Phys Chem Chem Phys. 2018 May 9;20(18):13068-13074. doi: 10.1039/c8cp01497c. PubMed PMID: 29713722. 2: Padmanabhan S, Jost M, Drennan CL, Elías-Arnanz M. A New Facet of Vitamin B(12): Gene Regulation by Cobalamin-Based Photoreceptors. Annu Rev Biochem. 2017 Jun 20;86:485-514. doi: 10.1146/annurev-biochem-061516-044500. Review. PubMed PMID: 28654327. 3: Li P, Gu Q, Wang Y, Yu Y, Yang L, Chen JV. Novel vitamin B(12)-producing Enterococcus spp. and preliminary in vitro evaluation of probiotic potentials. Appl Microbiol Biotechnol. 2017 Aug;101(15):6155-6164. doi: 10.1007/s00253-017-8373-7. Epub 2017 Jun 20. PubMed PMID: 28634850. 4: Danchin A, Braham S. Coenzyme B12 synthesis as a baseline to study metabolite contribution of animal microbiota. Microb Biotechnol. 2017 Jul;10(4):688-701. doi: 10.1111/1751-7915.12722. Epub 2017 Jun 14. PubMed PMID: 28612402; PubMed Central PMCID: PMC5481537. 5: Wang R, Yang Z, Luo J, Hsing IM, Sun F. B(12)-dependent photoresponsive protein hydrogels for controlled stem cell/protein release. Proc Natl Acad Sci U S A. 2017 Jun 6;114(23):5912-5917. doi: 10.1073/pnas.1621350114. Epub 2017 May 22. PubMed PMID: 28533376; PubMed Central PMCID: PMC5468657. 6: Plessl T, Bürer C, Lutz S, Yue WW, Baumgartner MR, Froese DS. Protein destabilization and loss of protein-protein interaction are fundamental mechanisms in cblA-type methylmalonic aciduria. Hum Mutat. 2017 Aug;38(8):988-1001. doi: 10.1002/humu.23251. Epub 2017 Jun 6. PubMed PMID: 28497574. 7: Polaski JT, Webster SM, Johnson JE Jr, Batey RT. Cobalamin riboswitches exhibit a broad range of ability to discriminate between methylcobalamin and adenosylcobalamin. J Biol Chem. 2017 Jul 14;292(28):11650-11658. doi: 10.1074/jbc.M117.787176. Epub 2017 May 8. PubMed PMID: 28483920; PubMed Central PMCID: PMC5512062. 8: Wang D, Zhang K, Han S, Yu L. PainVision® Apparatus for Assessment of Efficacy of Pulsed Radiofrequency Combined with Pharmacological Therapy in the Treatment of Postherpetic Neuralgia and Correlations with Measurements. Biomed Res Int. 2017;2017:5670219. doi: 10.1155/2017/5670219. Epub 2017 Mar 5. PubMed PMID: 28357404; PubMed Central PMCID: PMC5357555. 9: Bridwell-Rabb J, Drennan CL. Vitamin B(12) in the spotlight again. Curr Opin Chem Biol. 2017 Apr;37:63-70. doi: 10.1016/j.cbpa.2017.01.013. Epub 2017 Feb 3. Review. PubMed PMID: 28167430; PubMed Central PMCID: PMC5540639. 10: Lehman BP, Chowdhury C, Bobik TA. The N Terminus of the PduB Protein Binds the Protein Shell of the Pdu Microcompartment to Its Enzymatic Core. J Bacteriol. 2017 Mar 28;199(8). pii: e00785-16. doi: 10.1128/JB.00785-16. Print 2017 Apr 15. PubMed PMID: 28138097; PubMed Central PMCID: PMC5370416. 11: Pallares IG, Moore TC, Escalante-Semerena JC, Brunold TC. Spectroscopic Studies of the EutT Adenosyltransferase from Salmonella enterica: Evidence of a Tetrahedrally Coordinated Divalent Transition Metal Cofactor with Cysteine Ligation. Biochemistry. 2017 Jan 17;56(2):364-375. doi: 10.1021/acs.biochem.6b00750. Epub 2017 Jan 3. PubMed PMID: 28045498; PubMed Central PMCID: PMC5241240. 12: Miller NA, Wiley TE, Spears KG, Ruetz M, Kieninger C, Kräutler B, Sension RJ. Toward the Design of Photoresponsive Conditional Antivitamins B(12): A Transient Absorption Study of an Arylcobalamin and an Alkynylcobalamin. J Am Chem Soc. 2016 Nov 2;138(43):14250-14256. Epub 2016 Oct 24. PubMed PMID: 27797190. 13: Mattes TA, Escalante-Semerena JC. Salmonella enterica synthesizes 5,6-dimethylbenzimidazolyl-(DMB)-α-riboside. Why some Firmicutes do not require the canonical DMB activation system to synthesize adenosylcobalamin. Mol Microbiol. 2017 Jan;103(2):269-281. doi: 10.1111/mmi.13555. Epub 2016 Nov 22. PubMed PMID: 27748967; PubMed Central PMCID: PMC5218876. 14: Torres AC, Vannini V, Bonacina J, Font G, Saavedra L, Taranto MP. Cobalamin production by Lactobacillus coryniformis: biochemical identification of the synthetized corrinoid and genomic analysis of the biosynthetic cluster. BMC Microbiol. 2016 Oct 13;16(1):240. PubMed PMID: 27737643; PubMed Central PMCID: PMC5064896. 15: Shah T, Joshi K, Mishra S, Otiv S, Kumbar V. Molecular and cellular effects of vitamin B12 forms on human trophoblast cells in presence of excessive folate. Biomed Pharmacother. 2016 Dec;84:526-534. doi: 10.1016/j.biopha.2016.09.071. Epub 2016 Sep 28. PubMed PMID: 27693961. 16: Garabato BD, Lodowski P, Jaworska M, Kozlowski PM. Mechanism of Co-C photodissociation in adenosylcobalamin. Phys Chem Chem Phys. 2016 Jul 28;18(28):19070-82. doi: 10.1039/c6cp02136k. Epub 2016 Jun 30. PubMed PMID: 27356617. 17: Matsubara M, Urano N, Yamada S, Narutaki A, Fujii M, Kataoka M. Fermentative production of 1-propanol from d-glucose, l-rhamnose and glycerol using recombinant Escherichia coli. J Biosci Bioeng. 2016 Oct;122(4):421-6. doi: 10.1016/j.jbiosc.2016.03.011. Epub 2016 Apr 9. PubMed PMID: 27072298. 18: Liu JZ, Xu W, Chistoserdov A, Bajpai RK. Glycerol Dehydratases: Biochemical Structures, Catalytic Mechanisms, and Industrial Applications in 1,3-Propanediol Production by Naturally Occurring and Genetically Engineered Bacterial Strains. Appl Biochem Biotechnol. 2016 Jul;179(6):1073-100. doi: 10.1007/s12010-016-2051-6. Epub 2016 Mar 31. Review. PubMed PMID: 27033090. 19: Pallares IG, Moore TC, Escalante-Semerena JC, Brunold TC. Spectroscopic Studies of the EutT Adenosyltransferase from Salmonella enterica: Mechanism of Four-Coordinate Co(II)Cbl Formation. J Am Chem Soc. 2016 Mar 23;138(11):3694-704. doi: 10.1021/jacs.5b11708. Epub 2016 Mar 9. PubMed PMID: 26886077; PubMed Central PMCID: PMC4857612. 20: Kozlowski PM, Garabato BD, Lodowski P, Jaworska M. Photolytic properties of cobalamins: a theoretical perspective. Dalton Trans. 2016 Mar 21;45(11):4457-70. doi: 10.1039/c5dt04286k. Epub 2016 Feb 11. PubMed PMID: 26865262.