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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:08:05 UTC
HMDB IDHMDB00210
Secondary Accession NumbersNone
Metabolite Identification
Common NamePantothenic acid
DescriptionPantothenic acid, also called vitamin B5, is a water-soluble vitamin required to sustain life. Pantothenic acid is needed to form coenzyme-A (CoA), and is thus critical in the metabolism and synthesis of carbohydrates, proteins, and fats. Its name is derived from the Greek pantothen meaning "from everywhere" and small quantities of pantothenic acid are found in nearly every food, with high amounts in whole grain cereals, legumes, eggs, meat, and royal jelly.
Structure
Thumb
Synonyms
  1. (+)-Pantothenate
  2. (+)-Pantothenic acid
  3. (D)-(+)-Pantothenate
  4. (D)-(+)-Pantothenic acid
  5. (R)-pantothenate
  6. Chick antidermatitis factor
  7. D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-b-alanine
  8. D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-beta-alanine
  9. D-Pantothenate
  10. D-Pantothenic acid
  11. delta-Pantothenate
  12. delta-Pantothenic acid
  13. Pantothenate
  14. Vitamin B5
Chemical FormulaC9H17NO5
Average Molecular Weight219.235
Monoisotopic Molecular Weight219.110672659
IUPAC Name3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoic acid
Traditional IUPAC Namepantothenic acid
CAS Registry Number79-83-4
SMILES
CC(C)(CO)C(O)C(=O)NCCC(O)=O
InChI Identifier
InChI=1S/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)
InChI KeyGHOKWGTUZJEAQD-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlkylamines
Sub Class1,3-Aminoalcohols
Other Descriptors
  • pantothenic acids(ChEBI)
Substituents
  • Carboxamide Group
  • Carboxylic Acid
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent1,3-Aminoalcohols
Ontology
StatusDetected and Quantified
Origin
  • Drug
  • Food
Biofunction
  • Component of Pantothenate and CoA biosynthesis
  • Essential vitamins
ApplicationNot Available
Cellular locations
  • Extracellular
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility60.5 g/LALOGPS
logP-1.1ALOGPS
logP-1.4ChemAxon
logS-0.56ALOGPS
pKa (strongest acidic)4.35ChemAxon
pKa (strongest basic)-2.8ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count4ChemAxon
polar surface area106.86ChemAxon
rotatable bond count6ChemAxon
refractivity51.51ChemAxon
polarizability22.15ChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Liver
  • Most Tissues
  • Prostate
Pathways
NameSMPDB LinkKEGG Link
Beta-Alanine MetabolismSMP00007map00410
Pantothenate and CoA BiosynthesisSMP00027map00770
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.86 +/- 0.94 uMAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified4.91 +/- 0.38 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified3.6 (1.8-6.8) uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified1.3 (0.66-2.6) uMChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified4.13 (0.46-7.8) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified1.0 +/- 0.068 uMAdult (>18 years old)Not SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.37 (0.46-7.8) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
UrineDetected and Quantified1.0 +/- 0.63 umol/mmol creatinineChildren (1-13 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified2.7 +/- 0.9 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified1.2 +/- 0.4 umol/mmol creatinineAdult (>18 years old)FemaleNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified1.9 (0.6-4.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified11.16 +/- 8.88 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.96 +/- 0.47 uMAdult (>18 years old)Not Specified
Alcoholism
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.80 +/- 0.08 uMAdult (>18 years old)Not Specified
Alcoholism
details
Associated Disorders and Diseases
Disease References
Alcoholism
  1. Dastur DK, Santhadevi N, Quadros EV, Avari FC, Wadia NH, Desai MN, Bharucha EP: The B-vitamins in malnutrition with alcoholism. A model of intervitamin relationships. Br J Nutr. 1976 Sep;36(2):143-59. Pubmed: 182198
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011817
KNApSAcK IDNot Available
Chemspider ID963
KEGG Compound IDC00864
BioCyc IDPANTOTHENATE
BiGG ID36234
Wikipedia LinkPantothenic acid
NuGOwiki LinkHMDB00210
Metagene LinkHMDB00210
METLIN ID241
PubChem Compound988
PDB IDNot Available
ChEBI ID7916
References
Synthesis ReferenceKataoka, Michihiko; Shimizu, Sakayu; Doi, Yukiko; Yamada, Hideaki. Stereospecific reduction of ethyl 2'-ketopantothenate to ethyl D-(+)-pantothenate with microbial cells as a catalyst. Applied and Environmental Microbiology (1990), 56(11), 3595-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  2. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. Pubmed: 2026685
  3. Loftus EV Jr, Tremaine WJ, Nelson RA, Shoemaker JD, Sandborn WJ, Phillips SF, Hasan Y: Dexpanthenol enemas in ulcerative colitis: a pilot study. Mayo Clin Proc. 1997 Jul;72(7):616-20. Pubmed: 9212762
  4. Fry PC, Fox HM, Tao HG: Metabolic response to a pantothenic acid deficient diet in humans. J Nutr Sci Vitaminol (Tokyo). 1976;22(4):339-46. Pubmed: 1011047
  5. Roth-Maier DA, Wauer A, Stangl GI, Kirchgessner M: Precaecal digestibility of niacin and pantothenic acid from different foods. Int J Vitam Nutr Res. 2000 Jan;70(1):8-13. Pubmed: 10683755
  6. Preibisz J, Chlewicka I: [Digitalis treatment in acute myocardial infarct. Determination of serum drug levels] Pol Arch Med Wewn. 1977 Dec;58(6):585-91. Pubmed: 600836
  7. Guilarte TR: A radiometric microbiological assay for pantothenic acid in biological fluids. Anal Biochem. 1989 Apr;178(1):63-6. Pubmed: 2499220
  8. Srinivasan V, Christensen N, Wyse BW, Hansen RG: Pantothenic acid nutritional status in the elderly--institutionalized and noninstitutionalized. Am J Clin Nutr. 1981 Sep;34(9):1736-42. Pubmed: 7025609
  9. Eissenstat BR, Wyse BW, Hansen RG: Pantothenic acid status of adolescents. Am J Clin Nutr. 1986 Dec;44(6):931-7. Pubmed: 3788840
  10. Dastur DK, Santhadevi N, Quadros EV, Avari FC, Wadia NH, Desai MN, Bharucha EP: The B-vitamins in malnutrition with alcoholism. A model of intervitamin relationships. Br J Nutr. 1976 Sep;36(2):143-59. Pubmed: 182198

Enzymes

General function:
Involved in pantothenate kinase activity
Specific function:
Plays a role in the physiological regulation of the intracellular CoA concentration (By similarity).
Gene Name:
PANK4
Uniprot ID:
Q9NVE7
Molecular weight:
85990.12
Reactions
Adenosine triphosphate + Pantothenic acid → ADP + D-4'-Phosphopantothenatedetails
General function:
Involved in pantothenate kinase activity
Specific function:
May be the master regulator of the CoA biosynthesis (By similarity).
Gene Name:
PANK2
Uniprot ID:
Q9BZ23
Molecular weight:
30753.12
Reactions
Adenosine triphosphate + Pantothenic acid → ADP + D-4'-Phosphopantothenatedetails
General function:
Involved in pantothenate kinase activity
Specific function:
Plays a role in the physiological regulation of the intracellular CoA concentration (By similarity).
Gene Name:
PANK1
Uniprot ID:
Q8TE04
Molecular weight:
35578.965
Reactions
Adenosine triphosphate + Pantothenic acid → ADP + D-4'-Phosphopantothenatedetails
General function:
Involved in pantothenate kinase activity
Specific function:
Plays a role in the physiological regulation of the intracellular CoA concentration (By similarity).
Gene Name:
PANK3
Uniprot ID:
Q9H999
Molecular weight:
41093.695
Reactions
Adenosine triphosphate + Pantothenic acid → ADP + D-4'-Phosphopantothenatedetails
General function:
Involved in hydrolase activity, acting on carbon-nitrogen (but not peptide) bonds, in linear amides
Specific function:
Amidohydrolase that hydrolyzes specifically one of the carboamide linkages in D-pantetheine thus recycling pantothenic acid (vitamin B5) and releasing cysteamine.
Gene Name:
VNN1
Uniprot ID:
O95497
Molecular weight:
57011.16
Reactions
Pantetheine + Water → Pantothenic acid + Cysteaminedetails
General function:
Not Available
Specific function:
Amidohydrolase that hydrolyzes specifically one of the carboamide linkages in D-pantetheine thus recycling pantothenic acid (vitamin B5) and releasing cysteamine. Involved in the thymus homing of bone marrow cells. May regulate beta-2 integrin-mediated cell adhesion, migration and motility of neutrophil.
Gene Name:
VNN2
Uniprot ID:
O95498
Molecular weight:
33256.93
Reactions
Pantetheine + Water → Pantothenic acid + Cysteaminedetails
General function:
Not Available
Specific function:
Amidohydrolase that hydrolyzes specifically one of the carboamide linkages in D-pantetheine thus recycling pantothenic acid (vitamin B5) and releasing cysteamine.
Gene Name:
VNN3
Uniprot ID:
Q9NY84
Molecular weight:
Not Available
Reactions
Pantetheine + Water → Pantothenic acid + Cysteaminedetails