Record Information
Version1.0
Creation date2010-04-08 22:05:41 UTC
Update date2015-10-09 22:32:39 UTC
Primary IDFDB003166
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHydroxycobalamin
DescriptionVitamin (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 Number13422-51-0
Structure
Thumb
Synonyms
SynonymSource
a-(5,6-Dimethylbenzimidazolyl)hydroxocobamidebiospider
Alpha cobionebiospider
alpha-(5,6-Dimethylbenzimidazolyl)hydroxocobamidebiospider
AlphaRedisoldb_source
Axlonbiospider
Ciplamin hbiospider
Cobalexbiospider
Cobalin hbiospider
Cobinamide dihydroxide dihydrogen phosphate (ester) mono (inner salt) 3'-ester with 5,6-dimethyl -1-a-D-ribofuranosyl-1H-benzimidazole, 9CIdb_source
Cobinamide hydroxide ate 3'-ester with 5,6-dimethyl-1-a-D-ribofuranosylbenzimidazole inner saltHMDB
Cobinamide hydroxide ate 3'-ester with 5,6-dimethyl-1-alpha-delta-ribofuranosylbenzimidazole inner saltHMDB
Codroxomindb_source
Docclanbiospider
Docelanbiospider
Docevitabiospider
Droxominbiospider
Ducobee HYbiospider
Duradocebiospider
Duralta-12biospider
Hydrocobalaminbiospider
Hydrogrisevitbiospider
Hydrovitbiospider
Hydroxocobalamindb_source
Hydroxocobalaminebiospider
Hydroxycobalaminbiospider
Hydroxycobalamin, BAN, INN, USANdb_source
Lipflavonoiddb_source
Neo-Betalin 12db_source
Oh-CBLbiospider
Sytobex Hdb_source
Vibedendb_source
vitamin B-12bbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.055 g/LALOGPS
logP2.91ALOGPS
logS-4.4ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area465.43 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity419.97 m³·mol⁻¹ChemAxon
Polarizability133.74 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC62H89CoN13O15P
IUPAC namecobalt(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 IdentifierInChI=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 KeyOHTROZZULXOIDW-UHFFFAOYSA-K
Isomeric SMILESO=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 Weight1346.3551
Monoisotopic Molecular Weight1345.567070949
Classification
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrapyrroles and derivatives
Sub ClassCorrinoids
Direct ParentCobalamin derivatives
Alternative Parents
Substituents
  • Cobalamin
  • Metallotetrapyrrole skeleton
  • Tertiary aromatic amine
  • Pentose phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Diaminotoluene
  • Benzimidazole
  • Dialkyl phosphate
  • Benzenoid
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Tetrahydrofuran
  • Pyrroline
  • Pyrrolidine
  • Tertiary amine
  • Secondary alcohol
  • Ketimine
  • Amino acid or derivatives
  • Oxacycle
  • Azacycle
  • Organic transition metal salt
  • Organic 1,3-dipolar compound
  • Carbene-type 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Secondary amine
  • Enamine
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Carboxylic acid amidine
  • Amidine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic cobalt salt
  • Organic salt
  • Organic zwitterion
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 55.31%; H 6.66%; Co 4.38%; N 13.52%; O 17.83%; P 2.30%DFC
Melting Point200 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID4573922
ChEMBL IDNot Available
KEGG Compound IDC08230
Pubchem Compound ID5460373
Pubchem Substance IDNot Available
ChEBI ID27786
Phenol-Explorer IDNot Available
DrugBank IDDB00200
HMDB IDHMDB02308
CRC / DFC (Dictionary of Food Compounds) IDCRV53-B:CRV53-B
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDHydroxycobalamin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Methylmalonyl-CoA mutase, mitochondrialMUTP22033
Cob(I)yrinic acid a,c-diamide adenosyltransferase, mitochondrialMMABQ96EY8
Methylmalonic aciduria type A protein, mitochondrialMMAAQ8IVH4
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.