Human Metabolome Database Version 3.5

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Showing metabocard for Glutathionylcobalamin (HMDB02202)

Blood
Urine

Record Information

Version

3.5

Creation Date

2006-05-22 08:17:41 -0600

Update Date

2013-05-13 17:08:20 -0600

HMDB ID

HMDB02202

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Glutathionylcobalamin

Description

Potentially one of the biologically important forms of Vitamin B12; formed rapidly from aquacobalamin;.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Glutathionylcobalamin

Chemical Formula

C₇₂H₁₀₄CoN₁₆O₂₀PS

Average Molecular Weight

1635.663

Monoisotopic Molecular Weight

1634.640312244

IUPAC Name

1-{[2-(4-amino-4-carboxybutanamido)-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-46-hydroxy-12-(hydroxymethyl)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-15,20-dioxo-11,14,16-trioxa-2$l^{4},9,19,26,43$l^{4},44$l^{4},45$l^{4}-heptaaza-15$l^{5}-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(8),4,6,27,29(44),32,34(45),37,39(43)-decaene-1,1,1-tris(ylium)-15-olate

Traditional IUPAC Name

1-{[2-(4-amino-4-carboxybutanamido)-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}-30,35,40-tris(2-carbamoylethyl)-24,36,41-tris(carbamoylmethyl)-46-hydroxy-12-(hydroxymethyl)-5,6,17,23,28,31,31,36,38,41,42-undecamethyl-15,20-dioxo-11,14,16-trioxa-2$l^{4},9,19

CAS Registry Number

129128-04-7

SMILES

[N]=12C3=C(C)C4=[N]5C(C(CC(N)=O)(C)C4CCC(N)=O)(C)C4N6C7=C(C8=[N](C(=CC=1C(C3(C)CC(N)=O)CCC(N)=O)C(C)(C)C8CCC(N)=O)[Co+3]256(SCC(NC(CCC(C(=O)O)N)=O)C(=O)NCC(O)=O)[N]1=CN(C2C(C(C(CO)O2)OP([O-])(OC(C)CNC(=O)CCC7(C)C4CC(N)=O)=O)O)C2=CC(=C(C=C12)C)C)C

InChI Identifier

InChI=1S/C62H90N13O14P.C10H17N3O6S.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;11-5(10(18)19)1-2-7(14)13-6(4-20)9(17)12-3-8(15)16;/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);5-6,20H,1-4,11H2,(H,12,17)(H,13,14)(H,15,16)(H,18,19);/q;;+5/p-3

InChI Key

XRMSTELCCMHQSA-UHFFFAOYSA-K

Chemical Taxonomy

Kingdom

Organic Compounds

Super Class

Amino Acids, Peptides, and Analogues

Class

Peptides

Sub Class

N/A

Other Descriptors

Aromatic Heteropolycyclic Compounds

Substituents

Alpha Amino Acid Or Derivative
Benzimidazole
Carboxamide Group
Carboxylic Acid
Corrin
Dicarboxylic Acid Derivative
Diterpene
Enamine
Imidazole
Imine
Lactam
Metallotetrapyrrole Skeleton
N Acyl Alpha Amino Acid
N Acylglycine
N Substituted Alpha Amino Acid
Organic Hypophosphite
Organic Phosphite
Organic Transition Metal Moeity
Organometallic Compound
Oxolane
Phosphoric Acid Ester
Primary Alcohol
Primary Aliphatic Amine (Alkylamine)
Primary Carboxylic Acid Amide
Pyrrolidine
Pyrroline
Quaternary Ammonium Salt
Secondary Alcohol
Secondary Carboxylic Acid Amide
Tetrapyrrole Skeleton
Toluene

Direct Parent

Peptides

Ontology

Status

Expected and Not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

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
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	638.06 A²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	416.78	ChemAxon
Polarizability	160.95	ChemAxon
Formal Charge	2	ChemAxon
Physiological Charge	2	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Location

Not Available

Pathways

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

FDB022903

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

NuGOwiki Link

HMDB02202

Metagene Link

HMDB02202

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Brasch, Nicola E.; Hsu, Tsui-Ling Carolyn; Doll, Kenneth M.; Finke, Richard G. Synthesis and characterization of isolable thiolatocobalamin complexes relevant to coenzyme B12-dependent ribonucleoside triphosphate reductase. Journal of Inorganic Biochemistry (1999), 76(3-4), 197-209.

Material Safety Data Sheet (MSDS)

Not Available

General References

Pezacka E, Green R, Jacobsen DW: Glutathionylcobalamin as an intermediate in the formation of cobalamin coenzymes. Biochem Biophys Res Commun. 1990 Jun 15;169(2):443-50. Pubmed: 2357215
McCaddon A, Regland B, Hudson P, Davies G: Functional vitamin B(12) deficiency and Alzheimer disease. Neurology. 2002 May 14;58(9):1395-9. Pubmed: 12011287
Xia L, Cregan AG, Berben LA, Brasch NE: Studies on the formation of glutathionylcobalamin: any free intracellular aquacobalamin is likely to be rapidly and irreversibly converted to glutathionylcobalamin. Inorg Chem. 2004 Oct 18;43(21):6848-57. Pubmed: 15476387