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Details

Stereochemistry ABSOLUTE
Molecular Formula C62H88N13O14P.Co
Molecular Weight 1329.3478
Optical Activity UNSPECIFIED
Defined Stereocenters 14 / 14
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COBALAMIN

SMILES

[Co++].C[C@@H](CNC(=O)CC[C@]1(C)[C@@H](CC(N)=O)[C@H]2[N-]C1=C(C)C3=NC(=CC4=NC(=C(C)C5=N[C@]2(C)[C@@](C)(CC(N)=O)[C@@H]5CCC(N)=O)[C@@](C)(CC(N)=O)[C@@H]4CCC(N)=O)C(C)(C)[C@@H]3CCC(N)=O)OP([O-])(=O)O[C@@H]6[C@@H](CO)O[C@@H]([C@@H]6O)N7C=NC8=C7C=C(C)C(C)=C8

InChI

InChIKey=ASARMUCNOOHMLO-WLORSUFZSA-L
InChI=1S/C62H90N13O14P.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);/q;+2/p-2/t31-,34+,35+,36+,37-,41+,52+,53+,56+,57-,59+,60-,61-,62-;/m0./s1

HIDE SMILES / InChI
Molecular Formula C62H88N13O14P
Molecular Weight 1270.4146
Charge -2
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 14 / 14
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula Co
Molecular Weight 58.933195
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/23183296

Cobalamin (vitamin B12) is a cobalt-containing, B complex vitamin. B12 group (cobalamins) consist of cyanocobalamin, hydroxocobalamin, methylcobalamin and cobalamid. Neither plants nor animals are independently capable of constructing vitamin B12. Only bacteria and archaea have the enzymes required for its biosynthesis. Therefore, humans must absorb it from food. Excellent sources of B12 are foods of ruminant origin, so dairy and meat products play an important role in efforts to meet the official daily B12 intake. Vitamin B12 deficiency can potentially cause severe and irreversible damage, especially to the brain and nervous system. Vitamin B12 is used to treat vitamin B12 deficiency, including pernicious anemia.

CNS Activity

Originator

Merck Sharp & Dohme
57
Curator's Comment: in Glaxo Laboratories at the same time (1948 year). # Merck Sharp and Dohme

Approval Year

1921
1468
Targets

Targets

Primary TargetPharmacologyConditionPotency
Gastric intrinsic factor
1
Target ID: P27352
Gene ID: 2694.0
Gene Symbol: GIF
Target Organism: Homo sapiens (Human)
Binding Agent
1076
 0.1 µM [Kd]
Transcobalamin-2
1
Target ID: P20062
Gene ID: 6948.0
Gene Symbol: TCN2
Target Organism: Homo sapiens (Human)
Binding Agent
1076
Transcobalamin-1
1
Target ID: P20061
Gene ID: 6947.0
Gene Symbol: TCN1
Target Organism: Homo sapiens (Human)
Binding Agent
1076
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
511
Unknown

Approved Use

Unknown
Primary
Not Provided
511
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Decreased glutathione and elevated hair mercury levels are associated with nutritional deficiency-based autism in Oman.
2014-06
Prevalence and features of peripheral neuropathy in Parkinson's disease patients under different therapeutic regimens.
2014-01
Preventing Alzheimer's disease-related gray matter atrophy by B-vitamin treatment.
2013-06-04
Dietary supplementation with methyl donors reduces fatty liver and modifies the fatty acid synthase DNA methylation profile in rats fed an obesogenic diet.
2013-01
Mutations in ABCD4 cause a new inborn error of vitamin B12 metabolism.
2012-10
Evaluation of drugs with specific organ toxicities in organ-specific cell lines.
2012-03
Mechanism for prevention of alcohol-induced liver injury by dietary methyl donors.
2010-05
Methotrexate-induced myelopathy responsive to substitution of multiple folate metabolites.
2010-05
Mechanism of vitamin B12-responsiveness in cblC methylmalonic aciduria with homocystinuria.
2009-12
Influence of cobalamin on arsenic metabolism in Bangladesh.
2009-11
Delusional parasitosis in neurological patients.
2009-09-25
A case report of 46,XX,del(21)(q22) de novo deletion associated with Imerslund-Grasbeck syndrome.
1996-10
Risk factors for dideoxynucleoside-induced toxic neuropathy in patients with the human immunodeficiency virus infection.
1995-10-01
[Neonatal hemolytic and uremic syndrome, methylmalonic aciduria and homocystinuria due to intracellular vitamin B12 deficiency].
1994-08
The clinical potential of ademetionine (S-adenosylmethionine) in neurological disorders.
1994-08
[Neonatal hemolytic-uremic syndrome, methylmalonic aciduria and homocystinuria caused by intracellular vitamin B 12 deficiency. Value of etiological diagnosis].
1993-11
Uncommon chiasmal lesions: demyelinating disease, vasculitis, and cobalamin deficiency.
1993-08
Reversible dementia caused by vitamin B12 deficiency.
1993-02
Orthostatic hypotension induced by vitamin B12 deficiency.
1991-06
Maternal vegan diet causing a serious infantile neurological disorder due to vitamin B12 deficiency.
1991-01
[Regressive dementia-like syndrome caused by vitamin B 12 deficiency without hematologic abnormalities in a 92-year old patient].
1990-11-03
Glycosylated haemoglobin (HbA1c) in iron- and vitamin B12 deficiency.
1990-02
Sensory peripheral neuropathy of vitamin B12 deficiency: a primary demyelinating disease?
1988-01
A case of vitamin B12 deficiency megaloblastic anemia following total gastrectomy.
1988
Nutritional vitamin B12 deficiency in a breast-fed infant of a vegan-diet mother.
1986-04
Gaucher's disease: a case report with coincidental vitamin B12 deficiency anaemia.
1985-09
Acute organic psychosis caused by thyrotoxicosis and vitamin B12 deficiency: case report.
1985-03
[Agranulocytosis and impairment of liver functions terminating in death following vitamin B12 injection in pernicious anemia: report of a case].
1984-11
Folic acid and the nervous system.
1983-12
Totally vegetarian diets and infant nutrition.
1982-10
[A case of metabolic encephalopathy caused by vitamin B 12-dependent methylmalonicoaciduria].
1981-02
[A case of metabolic encephalopathy caused by vitamin B 12-dependent methylmalonicaciduria].
1981
Platelet monoamine oxidase activity in megaloblastic anaemia.
1980-10
The effect of vitamin B12 on tetracycline-induced fatty liver.
1980-09
The prevalence and nature of anemia among apparently normal subjects in Fiji.
1979-07
[Constitutional megaloblastic anaemia due to vitamin B12 deficit (Imerslund's disease). Report of a case. (author's transl)].
1979
[Anemia caused by folic acid or vitamin B-12 deficiency].
1978-12-01
Management of anemia in a general city hospital: value of chart review in establishing deficiencies in care.
1978-01-07
[Influence of methylcobalamin and cyanocobalamin on the neoplastic process in rats].
1977-09-01
Reversal of ineffective erythropoiesis in pernicious anaemia following vitamin B12 therapy.
1977-02
A qualitative platelet defect in severe vitamin B 12 deficiency. Response, hyperresponse, and thrombosis after vitamin B 12 therapy.
1973-04
[Diabetic polyneuropathy and myelopathy caused by vitamin B12 deficiency].
1973
Megaloblastic anemia after anticonvulsive therapy.
1972-11-09
[Neurologic disorders due to vitamin B 12 deficiency].
1972
Sensitivity to cyanocobalamin and hydroxocobalamin.
1971-05-01
Propionate and acetate excretion in chloramphenicol toxicity.
1968-09-21
Neuropsychiatric aspects of anticonvulsant megaloblastic anaemia.
1968-02-24
Optic neuropathy caused by vitamin-B12 deficiency in carriers of the fish tapeworm, Diphyllobothrium latum.
1966-03-26
Anemia due to vitamin B12 deficiency after treatment with folic acid in tropical sprue.
1966-02
[Cytogenetic and cytologic findings in enzymopenic panmyelopathies and pancytopenias. Familial myelopathy of Fanconi, glutathione-reductase deficiency anemia and megaloblastic B12 deficiency anemia].
1966
Patents

Patents

US2561364 A
1
US2643213 A
1
US8557792 B2
1

Sample Use Guides

In Vivo Use Guide
100% Daily Value is 2,4 ug
Route of Administration: Oral
In Vitro Use Guide
Intrinsic factor (IF(50)) is a cobalamin-transporting protein, which can be cleaved into two fragments: the 30 kDa N-terminal peptide IF(30) and the 20 kDa C-terminal glycopeptide IF(20). Experiments on binding of Cbl to IF(30), IF(20), and IF(50) revealed comparable association rate constants (k(+)(Cbl) = 4 x 10(6), 14 x 10(6), and 26 x 10(6) M(-1) s(-1), respectively), but the equilibrium dissociation constants were essentially different (K(Cbl) = 200 uM, 0.2 uM, and
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:14:05 GMT 2025
Edited
by admin
on Mon Mar 31 18:14:05 GMT 2025
Record UNII
8406EY2OQA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
COBALAMIN [VANDF]
Preferred Name English
COBALAMIN
VANDF  
Common Name English
Classification Tree Code System Code
LOINC 15039-1
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LOINC 26916-7
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LOINC 2132-9
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LOINC 16695-9
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LOINC 55850-2
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LOINC 14685-2
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LOINC 35201-3
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LIVERTOX NBK548710
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Code System Code Type Description
EVMPD
SUB32920
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PRIMARY
FDA UNII
8406EY2OQA
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PRIMARY
NCI_THESAURUS
C939
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PRIMARY
SMS_ID
100000125988
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PRIMARY
DRUG BANK
DB14098
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PRIMARY
CAS
13408-78-1
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PRIMARY
CHEBI
30411
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PRIMARY
RXCUI
42604
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PRIMARY
EPA CompTox
DTXSID101045573
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PRIMARY
DRUG CENTRAL
4603
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PRIMARY
DAILYMED
8406EY2OQA
Created by admin on Mon Mar 31 18:14:05 GMT 2025 , Edited by admin on Mon Mar 31 18:14:05 GMT 2025
PRIMARY
ECHA (EC/EINECS)
236-500-2
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PRIMARY
PUBCHEM
73415824
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PRIMARY
Related Record Type Details
Structure of COBALTOUS CATION
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of COBALAMIN
ACTIVE MOIETY
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