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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++].[H][C@]12[N-]C(=C(C)C3=NC(=CC4=NC(=C(C)C5=N[C@]1(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)[C@](C)(CCC(=O)NC[C@H](C)OP([O-])(=O)O[C@@H]6[C@@H](CO)O[C@@H]([C@@H]6O)N7C=NC8=C7C=C(C)C(C)=C8)[C@H]2CC(N)=O

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 Co
Molecular Weight 58.9332
Charge 2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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

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
86
Curator's Comment: in Glaxo Laboratories at the same time (1948 year). # Merck Sharp and Dohme

Approval Year

1921
1467
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
1064
 0.1 µM [Kd]
Transcobalamin-2
1
Target ID: P20062
Gene ID: 6948.0
Gene Symbol: TCN2
Target Organism: Homo sapiens (Human)
Binding Agent
1064
Transcobalamin-1
1
Target ID: P20061
Gene ID: 6947.0
Gene Symbol: TCN1
Target Organism: Homo sapiens (Human)
Binding Agent
1064
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
504
Unknown

Approved Use

Unknown
Primary
Not Provided
504
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Cytogenetic and cytologic findings in enzymopenic panmyelopathies and pancytopenias. Familial myelopathy of Fanconi, glutathione-reductase deficiency anemia and megaloblastic B12 deficiency anemia].
1966
Anemia due to vitamin B12 deficiency after treatment with folic acid in tropical sprue.
1966 Feb
Optic neuropathy caused by vitamin-B12 deficiency in carriers of the fish tapeworm, Diphyllobothrium latum.
1966 Mar 26
Neuropsychiatric aspects of anticonvulsant megaloblastic anaemia.
1968 Feb 24
Propionate and acetate excretion in chloramphenicol toxicity.
1968 Sep 21
Sensitivity to cyanocobalamin and hydroxocobalamin.
1971 May 1
[Neurologic disorders due to vitamin B 12 deficiency].
1972
Megaloblastic anemia after anticonvulsive therapy.
1972 Nov 9
[Diabetic polyneuropathy and myelopathy caused by vitamin B12 deficiency].
1973
A qualitative platelet defect in severe vitamin B 12 deficiency. Response, hyperresponse, and thrombosis after vitamin B 12 therapy.
1973 Apr
Reversal of ineffective erythropoiesis in pernicious anaemia following vitamin B12 therapy.
1977 Feb
Influence of methylcobalamin and cyanocobalamin on the neoplastic process in rats.
1977 Sep-Oct
[Anemia caused by folic acid or vitamin B-12 deficiency].
1978 Dec 1
Management of anemia in a general city hospital: value of chart review in establishing deficiencies in care.
1978 Jan 7
[Constitutional megaloblastic anaemia due to vitamin B12 deficit (Imerslund's disease). Report of a case. (author's transl)].
1979
The prevalence and nature of anemia among apparently normal subjects in Fiji.
1979 Jul
Platelet monoamine oxidase activity in megaloblastic anaemia.
1980 Oct
The effect of vitamin B12 on tetracycline-induced fatty liver.
1980 Sep
[A case of metabolic encephalopathy caused by vitamin B 12-dependent methylmalonicaciduria].
1981
[A case of metabolic encephalopathy caused by vitamin B 12-dependent methylmalonicoaciduria].
1981 Feb
Totally vegetarian diets and infant nutrition.
1982 Oct
Folic acid and the nervous system.
1983 Dec
[Agranulocytosis and impairment of liver functions terminating in death following vitamin B12 injection in pernicious anemia: report of a case].
1984 Nov
Acute organic psychosis caused by thyrotoxicosis and vitamin B12 deficiency: case report.
1985 Mar
Gaucher's disease: a case report with coincidental vitamin B12 deficiency anaemia.
1985 Sep
Nutritional vitamin B12 deficiency in a breast-fed infant of a vegan-diet mother.
1986 Apr
A case of vitamin B12 deficiency megaloblastic anemia following total gastrectomy.
1988
Sensory peripheral neuropathy of vitamin B12 deficiency: a primary demyelinating disease?
1988 Jan
Glycosylated haemoglobin (HbA1c) in iron- and vitamin B12 deficiency.
1990 Feb
[Regressive dementia-like syndrome caused by vitamin B 12 deficiency without hematologic abnormalities in a 92-year old patient].
1990 Nov 3
Maternal vegan diet causing a serious infantile neurological disorder due to vitamin B12 deficiency.
1991 Jan
Orthostatic hypotension induced by vitamin B12 deficiency.
1991 Jun
Uncommon chiasmal lesions: demyelinating disease, vasculitis, and cobalamin deficiency.
1993 Aug
Reversible dementia caused by vitamin B12 deficiency.
1993 Feb
[Neonatal hemolytic-uremic syndrome, methylmalonic aciduria and homocystinuria caused by intracellular vitamin B 12 deficiency. Value of etiological diagnosis].
1993 Nov
[Neonatal hemolytic and uremic syndrome, methylmalonic aciduria and homocystinuria due to intracellular vitamin B12 deficiency].
1994 Aug
The clinical potential of ademetionine (S-adenosylmethionine) in neurological disorders.
1994 Aug
Risk factors for dideoxynucleoside-induced toxic neuropathy in patients with the human immunodeficiency virus infection.
1995 Oct 1
A case report of 46,XX,del(21)(q22) de novo deletion associated with Imerslund-Grasbeck syndrome.
1996 Oct
Mechanism of vitamin B12-responsiveness in cblC methylmalonic aciduria with homocystinuria.
2009 Dec
Influence of cobalamin on arsenic metabolism in Bangladesh.
2009 Nov
Mechanism for prevention of alcohol-induced liver injury by dietary methyl donors.
2010 May
Methotrexate-induced myelopathy responsive to substitution of multiple folate metabolites.
2010 May
Delusional parasitosis in neurological patients.
2010 May-Jun
Evaluation of drugs with specific organ toxicities in organ-specific cell lines.
2012 Mar
Mutations in ABCD4 cause a new inborn error of vitamin B12 metabolism.
2012 Oct
Dietary supplementation with methyl donors reduces fatty liver and modifies the fatty acid synthase DNA methylation profile in rats fed an obesogenic diet.
2013 Jan
Preventing Alzheimer's disease-related gray matter atrophy by B-vitamin treatment.
2013 Jun 4
Prevalence and features of peripheral neuropathy in Parkinson's disease patients under different therapeutic regimens.
2014 Jan
Decreased glutathione and elevated hair mercury levels are associated with nutritional deficiency-based autism in Oman.
2014 Jun
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 Fri Dec 15 15:56:43 GMT 2023
Edited
by admin
on Fri Dec 15 15:56:43 GMT 2023
Record UNII
8406EY2OQA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
COBALAMIN
VANDF  
Common 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 Fri Dec 15 15:56:43 GMT 2023 , Edited by admin on Fri Dec 15 15:56:43 GMT 2023
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
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