Human Metabolome Database Version 3.5

Showing metabocard for Pantothenic acid (HMDB00210)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:05 -0700
HMDB ID HMDB00210
Secondary Accession Numbers None
Metabolite Identification
Common Name Pantothenic acid
Description Pantothenic 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C9H17NO5
Average Molecular Weight 219.235
Monoisotopic Molecular Weight 219.110672659
IUPAC Name 3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoic acid
Traditional IUPAC Name pantothenic acid
CAS Registry Number 79-83-4
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 Key GHOKWGTUZJEAQD-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Alkylamines
Sub Class 1,3-Aminoalcohols
Other Descriptors
  • pantothenic acids(ChEBI)
Substituents
  • Carboxamide Group
  • Carboxylic Acid
  • Primary Alcohol
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
Direct Parent 1,3-Aminoalcohols
Ontology
Status Detected and Quantified
Origin
  • Drug
  • Food
Biofunction
  • Component of Pantothenate and CoA biosynthesis
  • Essential vitamins
Application Not Available
Cellular locations
  • Extracellular
  • Mitochondria
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point < 25 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1000.0 mg/mL Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 60.5 g/L ALOGPS
LogP -1.12 ALOGPS
LogP -1.4 ChemAxon
LogS -0.56 ALOGPS
pKa (strongest acidic) 4.35 ChemAxon
pKa (strongest basic) -2.8 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 106.86 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 51.51 ChemAxon
Polarizability 22.15 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Mitochondria
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Most Tissues
  • Liver
  • Prostate
Pathways
Name SMPDB Link KEGG Link
Beta-Alanine Metabolism SMP00007 map00410 Link_out
Pantothenate and CoA Biosynthesis SMP00027 map00770 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
2.86 +/- 0.94 uM Adult (>18 years old) Female Normal
  • Geigy Scient...
Blood Detected and Quantified
4.91 +/- 0.38 uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
3.6 (1.8-6.8) uM Newborn (0-30 days old) Both Normal
  • Geigy Scient...
Blood Detected and Quantified
1.3 (0.66-2.6) uM Children (1-13 year old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
4.13 (0.46-7.8) uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Cerebrospinal Fluid (CSF) Detected and Quantified
1.0 +/- 0.068 uM Adult (>18 years old) Not Specified Normal
Cerebrospinal Fluid (CSF) Detected and Quantified
2.37 (0.46-7.8) uM Adult (>18 years old) Both Normal
  • Geigy Scient...
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Urine Detected and Quantified
1.0 +/- 0.63 umol/mmol creatinine Children (1-13 year old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
2.7 +/- 0.9 umol/mmol creatinine Adult (>18 years old) Male Normal
  • Geigy Scient...
Urine Detected and Quantified
1.2 +/- 0.4 umol/mmol creatinine Adult (>18 years old) Female Normal
  • Geigy Scient...
Urine Detected and Quantified
1.9 (0.6-4.4) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
11.16 +/- 8.88 umol/mmol creatinine Infant (0-1 year old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Cerebrospinal Fluid (CSF) Detected and Quantified 0.96 +/- 0.47 uM Adult (>18 years old) Not Specified Comment Alcoholism
Cerebrospinal Fluid (CSF) Detected and Quantified 0.80 +/- 0.08 uM Adult (>18 years old) Not Specified Comment Alcoholism
Associated Disorders and Diseases
Disease References
Alcoholism
  • 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 Link_out
      Associated OMIM IDs None
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB011817
      KNApSAcK ID Not Available
      Chemspider ID 963 Link_out
      KEGG Compound ID C00864 Link_out
      BioCyc ID PANTOTHENATE Link_out
      BiGG ID 36234 Link_out
      Wikipedia Link Pantothenic acid Link_out
      NuGOwiki Link HMDB00210 Link_out
      Metagene Link HMDB00210 Link_out
      METLIN ID 241 Link_out
      PubChem Compound 988 Link_out
      PDB ID Not Available
      ChEBI ID 7916 Link_out
      References
      Synthesis Reference Kataoka, 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. 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 Link_out
      2. 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 Link_out
      3. 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 Link_out
      4. 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 Link_out
      5. 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 Link_out
      6. Guilarte TR: A radiometric microbiological assay for pantothenic acid in biological fluids. Anal Biochem. 1989 Apr;178(1):63-6. Pubmed: 2499220 Link_out
      7. 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 Link_out
      8. Eissenstat BR, Wyse BW, Hansen RG: Pantothenic acid status of adolescents. Am J Clin Nutr. 1986 Dec;44(6):931-7. Pubmed: 3788840 Link_out
      9. 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 Link_out
      10. 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 Link_out

      Enzymes
      Name: Pantothenate kinase 4
      Reactions:
      Adenosine triphosphate + Pantothenic acid unknown ADP + D-4'-Phosphopantothenate details
      Gene Name: PANK4
      Uniprot ID: Q9NVE7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Pantothenate kinase 2, mitochondrial
      Reactions:
      Adenosine triphosphate + Pantothenic acid unknown ADP + D-4'-Phosphopantothenate details
      Gene Name: PANK2
      Uniprot ID: Q9BZ23 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Pantothenate kinase 1
      Reactions:
      Adenosine triphosphate + Pantothenic acid unknown ADP + D-4'-Phosphopantothenate details
      Gene Name: PANK1
      Uniprot ID: Q8TE04 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Pantothenate kinase 3
      Reactions:
      Adenosine triphosphate + Pantothenic acid unknown ADP + D-4'-Phosphopantothenate details
      Gene Name: PANK3
      Uniprot ID: Q9H999 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Pantetheinase
      Reactions:
      Pantetheine + Water unknown Pantothenic acid + Cysteamine details
      Gene Name: VNN1
      Uniprot ID: O95497 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Vascular non-inflammatory molecule 2
      Reactions:
      Pantetheine + Water unknown Pantothenic acid + Cysteamine details
      Gene Name: VNN2
      Uniprot ID: O95498 Link_out
      Protein Sequence: FASTA
      Name: Vascular non-inflammatory molecule 3
      Reactions:
      Pantetheine + Water unknown Pantothenic acid + Cysteamine details
      Gene Name: VNN3
      Uniprot ID: Q9NY84 Link_out