FComEx: Hydroxycobalamin (PC000780)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:39 UTC

Update date

2017-01-19 02:36:36 UTC

FoodComEx ID

PC000780

FoodDB Record

FDB003166

Chemical Information

Name

Hydroxycobalamin

Description

Vitamin (haematopoietic) A B 12 vitamin. It has been used therapeutically in the treatment and prevention of vitamin B 12 deficiency. -- Pubchem; Hydroxocobalamin (OHCbl) is a natural analog of vitamin B-12, a basic member of the cobalamin family of compounds. It has an intense red color. Vitamin B12 is a term that refers to a group of compounds called cobalamins that are available in the human body in a variety of mostly interconvertible forms. Together with folic acid, cobalamins are essential cofactors required for DNA synthesis in cells where chromosomal replication and division are occurring?most notably the bone marrow and myeloid cells. As a cofactor, cobalamins are essential for two cellular reactions: (1) the mitochondrial methylmalonylcoenzyme A mutase conversion of methylmalonic acid (MMA) to succinate, which links lipid and carbohydrate metabolism, and (2) activation of methionine synthase, which is the rate limiting step in the synthesis of methionine from homocysteine and tetrahydrofolate (Katzung, 1989).; Hydroxocobalamin is a synthetic, injectable form of Vitamin B12. Hydroxocobalamin is actually a precursor of two cofactors or vitamins (Vitamin B12 and Methylcobalamin) which are involved in various biological systems in man. Vitamin B12 is required for the conversion of methylmalonate to succinate. Deficiency of this enzyme could therefore interfere with the production of lipoprotein in myelin sheath tissue and so give rise to neurological lesions. The second cofactor, Methylcobalamin, is necessary for the conversion of homocysteine to methionine which is essential for the metabolism of folic acid. Deficiency of tetrahydrafolate leads to reduced synthesis of thymidylate resulting in reduced synthesis of DNA which is essential for cell maturation. Vitamin B12 is also concerned in the maintenance of sulphydryl groups in reduced form, deficiency leading to decreased amounts of reduced SH content of erythrocytes and liver cells. Overall, vitamin B12 acts as a coenzyme for various metabolic functions, including fat and carbohydrate metabolism and protein synthesis. It is necessary for growth, cell replication, hematopoiesis, and nucleoprotein as well as myelin synthesis. This is largely due to its effects on metabolism of methionine folic acid, and malonic acid.

CAS Number

13422-51-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
a-(5,6-Dimethylbenzimidazolyl)hydroxocobamide	biospider
Alpha cobione	biospider
alpha-(5,6-Dimethylbenzimidazolyl)hydroxocobamide	biospider
AlphaRedisol	db_source
Axlon	biospider
Ciplamin h	biospider
Cobalex	biospider
Cobalin h	biospider
Cobinamide dihydroxide dihydrogen phosphate (ester) mono (inner salt) 3'-ester with 5,6-dimethyl -1-a-D-ribofuranosyl-1H-benzimidazole, 9CI	db_source
Cobinamide hydroxide ate 3'-ester with 5,6-dimethyl-1-a-D-ribofuranosylbenzimidazole inner salt	HMDB
Cobinamide hydroxide ate 3'-ester with 5,6-dimethyl-1-alpha-delta-ribofuranosylbenzimidazole inner salt	HMDB
Codroxomin	db_source
Docclan	biospider
Docelan	biospider
Docevita	biospider
Droxomin	biospider
Ducobee HY	biospider
Duradoce	biospider
Duralta-12	biospider
Hydrocobalamin	biospider
Hydrogrisevit	biospider
Hydrovit	biospider
Hydroxocobalamin	db_source
Hydroxocobalamine	biospider
Hydroxycobalamin	biospider
Hydroxycobalamin, BAN, INN, USAN	db_source
Lipflavonoid	db_source
Neo-Betalin 12	db_source
Oh-CBL	biospider
Sytobex H	db_source
Vibeden	db_source
vitamin B-12b	biospider

Chemical Formula

C62H89CoN13O15P

IUPAC name

cobalt(3+) ion 3-[13-(3-azanidyl-3-oxopropyl)-4-{2-[(2-{[hydroxy({[4-hydroxy-2-(hydroxymethyl)-5-(5-methyl-1-methylidene-3H-1lambda5,3-benzodiazol-3-yl)oxolan-3-yl]oxy})phosphoryl]oxy}propyl)-C-hydroxycarbonimidoyl]ethyl}-18-[2-(C-hydroxycarbonimidoyl)ethyl]-3,14,19-tris[(C-hydroxycarbonimidoyl)methyl]-1,4,6,9,9,14,16,19-octamethyl-20,21,22,23-tetraazapentacyclo[15.2.1.1^{2,5}.1^{7,10}.1^{12,15}]tricosa-5(23),6,10(22),11,15(21),16-hexaen-8-yl]propanecarboximidate hydrate

InChI Identifier

InChI=1S/C62H90N13O14P.Co.H2O/c1-30-12-16-39-40(22-30)75(29-74(39)11)57-52(84)53(41(28-76)87-57)89-90(85,86)88-31(2)27-69-49(83)20-21-59(7)37(23-46(66)80)56-62(10)61(9,26-48(68)82)36(15-19-45(65)79)51(73-62)33(4)55-60(8,25-47(67)81)34(13-17-43(63)77)38(70-55)24-42-58(5,6)35(14-18-44(64)78)50(71-42)32(3)54(59)72-56;;/h12,16,22,24,29,31,34-37,41,52-53,56-57,76,84H,11,13-15,17-21,23,25-28H2,1-10H3,(H15,63,64,65,66,67,68,69,70,71,72,73,77,78,79,80,81,82,83,85,86);;1H2/q;+3;/p-3

InChI Key

OHTROZZULXOIDW-UHFFFAOYSA-K

Isomeric SMILES

O=C(CCC1C2=C(C3=[N]4C(=CC5=[N]6C(C(C5(C)C)CCC(=O)N)=C(C5=[N]7C8C(N2[Co+]467(C[N]2=CN(C4=CC(C)=CC=C24)C2OC(CO)C(OP(=O)(OC(C)CNC(=O)CCC5(C)C8CC(=O)N)[O-])C2O)O)(C1(CC(=O)N)C)C)C)C(CCC(N)=O)C3(CC(=O)N)C)C)N

Average Molecular Weight

1346.3551

Monoisotopic Molecular Weight

1345.567070949

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrapyrroles and derivatives

Sub Class

Corrinoids

Direct Parent

Cobalamin derivatives

Alternative Parents