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[(2R,3S,4R)-5-(5,6-dimethylbenzimidazol-1-yl)-2-(hydroxymethyl)-4-oxidanyl-oxolan-3-yl] [(2R)-1-[3-[(1R,2R,3R,5Z,7S,10Z,12S,13S,15Z,17S,18S,19R)-2,13,18-tris(2-azanyl-2-oxidanylidene-ethyl)-7,12,17-tris(3-azanyl-3-oxidanylidene-propyl)-3,5,8,8,3,15,18,19-octamethyl-2,7,12,17-tetrahydro-1H-corrin-24-id-3-yl]propanoylamino]propan-2-yl] phosphate

PubChem CID
118701016
Structure
[(2R,3S,4R)-5-(5,6-dimethylbenzimidazol-1-yl)-2-(hydroxymethyl)-4-oxidanyl-oxolan-3-yl] [(2R)-1-[3-[(1R,2R,3R,5Z,7S,10Z,12S,13S,15Z,17S,18S,19R)-2,13,18-tris(2-azanyl-2-oxidanylidene-ethyl)-7,12,17-tris(3-azanyl-3-oxidanylidene-propyl)-3,5,8,8,3,15,18,19-octamethyl-2,7,12,17-tetrahydro-1H-corrin-24-id-3-yl]propanoylamino]propan-2-yl] phosphate_small.png
Molecular Formula
Synonyms
  • vitamin B12
  • [(2R,3S,4R)-5-(5,6-dimethylbenzimidazol-1-yl)-2-(hydroxymethyl)-4-oxidanyl-oxolan-3-yl] [(2R)-1-[3-[(1R,2R,3R,5Z,7S,10Z,12S,13S,15Z,17S,18S,19R)-2,13,18-tris(2-azanyl-2-oxidanylidene-ethyl)-7,12,17-tris(3-azanyl-3-oxidanylidene-propyl)-3,5,8,8,3,15,18,19-octamethyl-2,7,12,17-tetrahydro-1H-corrin-24-id-3-yl]propanoylamino]propan-2-yl] phosphate
Molecular Weight
1355.4 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Parent Compound
Dates
  • Create:
    2016-02-25
  • Modify:
    2025-01-18
Description
vitamin B12 is a metabolite found in or produced by Escherichia coli (strain K12, MG1655).
A cobalt-containing coordination compound produced by intestinal micro-organisms and found also in soil and water. Higher plants do not concentrate vitamin B 12 from the soil and so are a poor source of the substance as compared with animal tissues. INTRINSIC FACTOR is important for the assimilation of vitamin B 12.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
[(2R,3S,4R)-5-(5,6-dimethylbenzimidazol-1-yl)-2-(hydroxymethyl)-4-oxidanyl-oxolan-3-yl] [(2R)-1-[3-[(1R,2R,3R,5Z,7S,10Z,12S,13S,15Z,17S,18S,19R)-2,13,18-tris(2-azanyl-2-oxidanylidene-ethyl)-7,12,17-tris(3-azanyl-3-oxidanylidene-propyl)-3,5,8,8,3,15,18,19-octamethyl-2,7,12,17-tetrahydro-1H-corrin-24-id-3-yl]propanoylamino]propan-2-yl] phosphate.png

1.2 3D Status

Conformer generation is disallowed since too many atoms, MMFF94s unsupported element, too flexible, mixture or salt

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

cobalt(3+);[(2R,3S,4R)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2R)-1-[3-[(2R,3R,4Z,7S,9Z,12S,13S,14Z,17S,18S,19R)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7,12,17-tetrahydro-1H-corrin-21-id-3-yl]propanoylamino]propan-2-yl] phosphate;cyanide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.05.07)

2.1.2 InChI

InChI=1S/C62H90N13O14P.CN.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;1-2;/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;-1;+3/p-2/t31-,34-,35-,36-,37+,41-,52-,53-,56?,57?,59-,60+,61+,62+;;/m1../s1
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.3 InChIKey

FDJOLVPMNUYSCM-DHLJCVJLSA-L
Computed by InChI 1.0.6 (PubChem release 2021.05.07)

2.1.4 SMILES

CC1=CC2=C(C=C1C)N(C=N2)C3[C@@H]([C@@H]([C@H](O3)CO)OP(=O)([O-])O[C@H](C)CNC(=O)CC[C@@]\4([C@H](C5[C@]6([C@@]([C@@H](C(=N6)/C(=C\7/[C@@]([C@@H](C(=N7)/C=C\8/C([C@@H](C(=N8)/C(=C4\[N-]5)/C)CCC(=O)N)(C)C)CCC(=O)N)(C)CC(=O)N)/C)CCC(=O)N)(C)CC(=O)N)C)CC(=O)N)C)O.[C-]#N.[Co+3]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C63H88CoN14O14P
Computed by PubChem 2.1 (PubChem release 2021.05.07)

2.3 Other Identifiers

2.3.1 CAS

68-19-9

2.3.2 Deprecated CAS

11037-08-4, 24436-34-8, 8023-26-5, 8039-03-0

2.3.3 Metabolomics Workbench ID

2.3.4 RXCUI

2.3.5 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • B 12, Vitamin
  • B12, Vitamin
  • Cobalamin
  • Cobalamins
  • Cyanocobalamin
  • Eritron
  • Vitamin B 12
  • Vitamin B12

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
1355.4 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Donor Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Hydrogen Bond Acceptor Count
Property Value
21
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Rotatable Bond Count
Property Value
26
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Exact Mass
Property Value
1354.567399 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
1354.567399 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
476 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Heavy Atom Count
Property Value
93
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
3150
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.05.07)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
12
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
3
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2015.09.10)

3.2 Experimental Properties

3.2.1 Physical Description

Dark red odorless solid; Hygroscopic; [Merck Index] Dark red powder; [Sigma-Aldrich MSDS]

3.3 Chemical Classes

Biological Agents -> Vitamins and Derivatives

3.3.1 Drugs

3.3.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Vitamin B Complex; Vitamins

5 Drug and Medication Information

5.1 Drug Classes

Breast Feeding; Lactation; Milk, Human; Vitamin B Complex; Vitamins

5.2 Clinical Trials

5.2.1 ClinicalTrials.gov

5.2.2 EU Clinical Trials Register

6 Pharmacology and Biochemistry

6.1 MeSH Pharmacological Classification

Vitamin B Complex
A group of water-soluble vitamins, some of which are COENZYMES. (See all compounds classified as Vitamin B Complex.)

7 Use and Manufacturing

7.1 Uses

Sources/Uses
Produced by bacteria, cobalamins (hydroxocobalamin and cyanocobalamin) are analogs of vitamin B12 that differ only in the beta-ligand of the cobalt; Found in fish, meat, liver, and dairy products, but not in plants; Also occur naturally in soil, water, activated sewage sludge, and manure; Used as a vitamin (hematopoietic); [Merck Index] Used as a nutritional supplement and stabilizer or thickener for foods; [FDA] Permitted for use as an inert ingredient in non-food pesticide products; [EPA] Used to perform Schilling's test (pernicious anemia or other malabsorption disorders), as a medicine, nutrient, and animal feed supplement; [HSDB] Hydroxocabalamin is used to treat cyanide poisoning. [Olson, p. 563]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
Olson - Olson KR (ed). Poisoning & Drug Overdose, 7th Ed. New York: Lange Medical Books/McGraw-Hill, 2018., p. 563
Industrial Processes with risk of exposure
Farming (Feed Additives) [Category: Industry]

7.2 General Manufacturing Information

EPA TSCA Commercial Activity Status
Vitamin B12: ACTIVE

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 Hazards Summary

Patients treated with IV hydroxocobalamin have red urine and erythema; [Olson, p. 563] May cause irritation; [Sigma-Aldrich MSDS]
Olson - Olson KR (ed). Poisoning & Drug Overdose, 7th Ed. New York: Lange Medical Books/McGraw-Hill, 2018., p. 563

8.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Vitamin B12
New Zealand EPA Inventory of Chemical Status
Vitamin B12: Does not have an individual approval but may be used under an appropriate group standard

9 Toxicity

9.1 Toxicological Information

9.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Vitamin B12 is a normal component of human milk. The recommended daily intake in lactating women is 2.8 mcg and for infants aged 6 months or less is 0.4 mcg. Some authorities recommend 5.5 mcg per day during lactation. Supplementation may be necessary to achieve these recommended daily intakes or to correct a known deficiency. Low doses (1 to 10 mcg) of vitamin B12 found in B complex or prenatal vitamins increase milk levels only slightly. Higher daily doses of 50 to 250 mcg are needed in cases of maternal deficiency. The breastfed infant is not exposed to excessive vitamin B12 in such cases, and their vitamin B12 status should improve if it was previously inadequate.

Poor health outcomes in infants with vitamin B12 deficiency include anemia, abnormal skin and hair development, convulsions, weak muscle tone, failure to thrive, mental developmental delay, and potentially abnormal movements. Well-recognized at risk groups are exclusively breastfed infants of mothers with B12 deficiency due to minimal or no dietary intake of animal products or pernicious anemia caused by a maternal malabsorption of B12. Infant vitamin B12 status can be improved through maternal B12 supplementation during pregnancy and lactation. Deficient mothers who miss the opportunity to supplement during pregnancy should still be encouraged to supplement during early lactation since infant vitamin B12 status correlates with milk vitamin B12 levels in breastfed infants up to 6 months of age. Although there are cases reported of exclusively breastfed infants with vitamin B12 deficiency having biochemical and clinical improvement through adequate maternal supplementation alone, direct supplementation of the infant is recommended when such treatments are available.

◉ Effects in Breastfed Infants

Twelve exclusively breastfed infants between 4 and 11 months of age had biochemical, hematological and clinical findings consistent with vitamin B12 deficiency. Their mothers received a 50 mcg single dose of intramuscular vitamin B12. Within 5 to 8 days after the dose, the infants experienced significantly increased hemoglobin and reticulocyte counts, normoblastic erythropoiesis, improved mental status, regression of abnormal skin pigmentation, and reduction in tremors.

Three hundred sixty-six pregnant women in India received 50 mcg of oral vitamin B12 or placebo capsules once daily beginning during their first trimester of pregnancy and continuing until 6 weeks postpartum. Among 218 infants that underwent neurodevelopment testing at 30 months of age, those born to mothers randomized to vitamin B12 had higher expressive language scores than the placebo group when adjusted for baseline maternal vitamin B12 deficiency. Cognitive, receptive language and motor scores were not different between the two groups. Neurophysiological assessments were then conducted at 6 years of age and there were no differences in the measured brain activity between the two groups.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Chemical Co-Occurrences in Literature

10.4 Chemical-Gene Co-Occurrences in Literature

10.5 Chemical-Disease Co-Occurrences in Literature

11 Classification

11.1 MeSH Tree

11.2 EPA TSCA and CDR Classification

12 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. EPA Chemicals under the TSCA
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  3. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  4. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  5. Drugs and Lactation Database (LactMed)
  6. E. coli Metabolome Database (ECMDB)
    LICENSE
    ECMDB is offered to the public as a freely available resource.
    https://ecmdb.ca/citations
  7. EU Clinical Trials Register
  8. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  9. Metabolomics Workbench
  10. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  11. Wikipedia
  12. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  13. PubChem
  14. NCBI
CONTENTS