Record Information
Version2.0
Creation Date2012-05-31 10:23:43 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00210
Identification
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
Synonyms:
  • (+)-Pantothenate
  • (+)-Pantothenic acid
  • (R)-pantothenic acid
  • (D)-(+)-Pantothenate
  • (D)-(+)-Pantothenic acid
  • (R)-pantothenate
  • (R)-pantothenic acid
  • Chick antidermatitis factor
  • D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-b-alanine
  • D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-beta-alanine
  • D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-β-alanine
  • D-Pantothenate
  • D-Pantothenic acid
  • Delta-Pantothenate
  • Delta-Pantothenic acid
  • Pantothenate
  • Vitamin B5
  • Vitamin B5
  • δ-Pantothenate
  • δ-Pantothenic acid
Chemical Formula:C9H17NO5
Weight:Average: 219.235
Monoisotopic: 219.110672659
InChI Key:GHOKWGTUZJEAQD-UHFFFAOYSA-N
InChI: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)
CAS number:79-83-4
IUPAC Name:3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoic acid
Traditional IUPAC Name:DL-pantothenic acid
SMILES:CC(C)(CO)C(O)C(=O)NCCC(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as polyols. These are organic compounds containing more than one hydroxyl groups.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassAlcohols and polyols
Sub ClassPolyols
Direct ParentPolyols
Alternative Parents
Substituents
  • Secondary alcohol
  • Polyol
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary alcohol
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:< 25 °C
Experimental Properties:
PropertyValueSource
Water Solubility:1000.0 mg/mL [MERCK INDEX (1996)]PhysProp
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 Area106.86 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity51.51 m³·mol⁻¹ChemAxon
Polarizability21.92 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Pantothenate and CoA biosynthesisPW000828 ThumbThumb?image type=greyscaleThumb?image type=simple
beta-Alanine metabolismPW000896 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0zfu-1950000000-e17ccf50735fd5171fc4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f6t-3921000000-6a2222a87b5ffd328ceeView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-9785638e8fe83ade2497View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0zfr-0920000000-5f3d78d9671cf3e9e436View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0910000000-1ad24073d09589d69733View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-8910000000-e9fba0c36e325b52e91fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00fs-9665200000-38141a3794d53c37aba5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0090000000-4077cb3290a3d501c967View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000j-9520000000-21cefac627d830ed5bbfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000j-9400000000-d7cac2e845877b5d4c45View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-a56de6ea4cc94ead9287View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-958b1047fc59d5fa55abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-9100000000-5cf3012f98b80b72b87cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ks-9330000000-5220625c440a0e4d0e1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ks-9330000000-da413d79b085b05c74faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000j-9410000000-e4934ca5cda48554f8bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0090000000-d74155da6ca6fff432c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9560000000-663aa7cea0b521907df1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-006x-9200000000-475c18425c9352988ee1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01bc-9000000000-afcfa162e86332d3cfa2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9000000000-421f28522574e5fa8eaeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0f6x-9470000000-cfd10935dbbb59770f3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-460a4bec2421708c0e18View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-2190000000-6eec23d0d7031fc1e28bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dl-9460000000-a6391c9eace085a7cd68View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-006x-9450000000-f677ff82e7d7f3f58ba1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fe0-9230000000-5d3b471f56b2c2e5535bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9200000000-12b30ec690e561fbee15View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-167b8eb76324b5c3850aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3790000000-e2e626db270df267d7dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fki-7910000000-01cff3f952409e9e9550View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9200000000-a56f834482e2844f6924View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • Eissenstat BR, Wyse BW, Hansen RG: Pantothenic acid status of adolescents. Am J Clin Nutr. 1986 Dec;44(6):931-7. Pubmed: 3788840
  • 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
  • Guilarte TR: A radiometric microbiological assay for pantothenic acid in biological fluids. Anal Biochem. 1989 Apr;178(1):63-6. Pubmed: 2499220
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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)
External Links:
ResourceLink
CHEBI ID16454
HMDB IDHMDB00210
Pubchem Compound ID6613
Kegg IDC00864
ChemSpider ID963
WikipediaPantothenic acid
BioCyc IDPANTOTHENATE
EcoCyc IDPANTOTHENATE

Enzymes

General function:
Involved in pantothenate kinase activity
Specific function:
ATP + (R)-pantothenate = ADP + (R)-4'- phosphopantothenate
Gene Name:
coaA
Uniprot ID:
P0A6I3
Molecular weight:
36359
Reactions
ATP + (R)-pantothenate = ADP + (R)-4'-phosphopantothenate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the condensation of pantoate with beta-alanine in an ATP-dependent reaction via a pantoyl-adenylate intermediate
Gene Name:
panC
Uniprot ID:
P31663
Molecular weight:
31597
Reactions
ATP + (R)-pantoate + beta-alanine = AMP + diphosphate + (R)-pantothenate.

Transporters

General function:
Involved in sodium ion transmembrane transporter activity
Specific function:
Catalyzes the sodium-dependent uptake of extracellular pantothenate
Gene Name:
panF
Uniprot ID:
P16256
Molecular weight:
51717
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368