Record Information
Version1.0
Creation Date2016-05-26 00:02:31 UTC
Update Date2016-11-09 01:18:33 UTC
Accession NumberCHEM027871
Identification
Common Name(R)-Pantothenic acid
ClassSmall Molecule
Description(r)-pantothenate, also known as (+)-pantothenic acid or vitamin b5, is a member of the class of compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl) (r)-pantothenate is soluble (in water) and a weakly acidic compound (based on its pKa). (r)-pantothenate can be found in a number of food items such as spirulina, nance, cereals and cereal products, and sparkleberry, which makes (r)-pantothenate a potential biomarker for the consumption of these food products (r)-pantothenate can be found primarily in blood and urine (r)-pantothenate exists in all eukaryotes, ranging from yeast to humans.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
Synonyms
ValueSource
(+)-Pantothenic acidChEBI
(R)-N-(2,4-Dihydroxy-3,3-dimethyl-1-oxobutyl)-beta-alanineChEBI
Chick antidermatitis factorChEBI
D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-beta-alanineChEBI
D-(+)-Pantothenic acidChEBI
D-Pantothenic acidChEBI
N-[(2R)-2,4-Dihydroxy-3,3-dimethylbutanoyl]-beta-alanineChEBI
PANTOTHENOIC ACIDChEBI
Vitamin b5ChEBI
(R)-PantothenateKegg
Pantothen pharmaselectKegg
(+)-PantothenateGenerator
(R)-N-(2,4-Dihydroxy-3,3-dimethyl-1-oxobutyl)-b-alanineGenerator
(R)-N-(2,4-Dihydroxy-3,3-dimethyl-1-oxobutyl)-β-alanineGenerator
D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-b-alanineGenerator
D(+)-N-(2,4-Dihydroxy-3,3-dimethylbutyryl)-β-alanineGenerator
D-(+)-PantothenateGenerator
D-PantothenateGenerator
N-[(2R)-2,4-Dihydroxy-3,3-dimethylbutanoyl]-b-alanineGenerator
N-[(2R)-2,4-Dihydroxy-3,3-dimethylbutanoyl]-β-alanineGenerator
PANTOTHENOateGenerator
(R)-Pantothenic acidGenerator
PantothenateGenerator
b5, VitaminHMDB
Pantothenate, zincHMDB
b 5, VitaminHMDB
Calcium pantothenateHMDB
Pantothenate, calciumHMDB
Vitamin b 5HMDB
DexolHMDB
Zinc pantothenateHMDB
Pantothenic acidChEBI
Chemical FormulaC9H17NO5
Average Molecular Mass219.235 g/mol
Monoisotopic Mass219.111 g/mol
CAS Registry Number599-54-2
IUPAC Name3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanoic acid
Traditional Name(+)-pantothenic acid
SMILESCC(C)(CO)C(O)C(=O)NCCC(O)=O
InChI IdentifierInChI=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
Description belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassAlcohols and polyols
Direct ParentSecondary alcohols
Alternative Parents
Substituents
  • Secondary alcohol
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Polyol
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carbonyl group
  • Primary alcohol
  • Organic nitrogen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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 Area106.86 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity51.51 m³·mol⁻¹ChemAxon
Polarizability21.99 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0zfu-1950000000-e17ccf50735fd5171fc4Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f6t-3921000000-6a2222a87b5ffd328ceeSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-9785638e8fe83ade2497Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0zfr-0920000000-5f3d78d9671cf3e9e436Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0910000000-1ad24073d09589d69733Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-8910000000-e9fba0c36e325b52e91fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00fs-9665200000-38141a3794d53c37aba5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0090000000-4077cb3290a3d501c967Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000j-9520000000-21cefac627d830ed5bbfSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000j-9400000000-d7cac2e845877b5d4c45Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-a56de6ea4cc94ead9287Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-958b1047fc59d5fa55abSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-9100000000-5cf3012f98b80b72b87cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ks-9330000000-5220625c440a0e4d0e1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ks-9330000000-da413d79b085b05c74faSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000j-9410000000-e4934ca5cda48554f8bcSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0090000000-d74155da6ca6fff432c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9560000000-663aa7cea0b521907df1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-006x-9200000000-475c18425c9352988ee1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01bc-9000000000-afcfa162e86332d3cfa2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9000000000-421f28522574e5fa8eaeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0f6x-9470000000-cfd10935dbbb59770f3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-460a4bec2421708c0e18Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-2190000000-6eec23d0d7031fc1e28bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dl-9460000000-a6391c9eace085a7cd68Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-006x-9450000000-f677ff82e7d7f3f58ba1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fe0-9230000000-5d3b471f56b2c2e5535bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9200000000-12b30ec690e561fbee15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-167b8eb76324b5c3850aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3790000000-e2e626db270df267d7dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fki-7910000000-01cff3f952409e9e9550Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9200000000-a56f834482e2844f6924Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000210
FooDB IDFDB030151
Phenol Explorer IDNot Available
KNApSAcK IDC00001550
BiGG IDNot Available
BioCyc IDPANTOTHENATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPantothenic_Acid
Chemspider ID6361
ChEBI ID46905
PubChem Compound ID6613
Kegg Compound IDC00864
YMDB IDYMDB00203
ECMDB IDECMDB23013
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. 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.
3. 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.
4. 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.
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.
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.
7. Guilarte TR: A radiometric microbiological assay for pantothenic acid in biological fluids. Anal Biochem. 1989 Apr;178(1):63-6.
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.
9. Eissenstat BR, Wyse BW, Hansen RG: Pantothenic acid status of adolescents. Am J Clin Nutr. 1986 Dec;44(6):931-7.
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.
11. 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. doi: 10.1038/nature07762.
12. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=12664639
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=14675432
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=15065769
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=15912738
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=16042590
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=17023940
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=17439666
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=17913047
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=19959891
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=22052867
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=22468352
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=5352084