Showing metabocard for Pantothenic acid (BMDB0000210)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:26:45 UTC
Update Date2020-06-04 20:47:49 UTC
MCDB ID BMDB0000210
Secondary Accession Numbers
  • BMDB00210
Metabolite Identification
Common NamePantothenic acid
Description(R)-Pantothenic acid, also known as vitamin B5 or (R)-pantothenate, 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) (R)-Pantothenic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule (R)-Pantothenic acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight219.235
Monoisotopic Molecular Weight219.110672659
IUPAC Name3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanoic acid
Traditional Name(+)-pantothenic acid
CAS Registry Number79-83-4
SMILES
CC(C)(CO)[C@@H](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)/t7-/m0/s1
InChI KeyGHOKWGTUZJEAQD-ZETCQYMHSA-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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0zfu-1950000000-e17ccf50735fd5171fc42014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0f6t-3921000000-6a2222a87b5ffd328cee2014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-9785638e8fe83ade24972017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0zfr-0920000000-5f3d78d9671cf3e9e4362017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0910000000-1ad24073d09589d697332017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-8910000000-e9fba0c36e325b52e91f2016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00fs-9665200000-38141a3794d53c37aba52017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-014i-0090000000-4077cb3290a3d501c9672017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000j-9520000000-21cefac627d830ed5bbf2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000j-9400000000-d7cac2e845877b5d4c452017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-a56de6ea4cc94ead92872017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-9000000000-958b1047fc59d5fa55ab2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-9100000000-5cf3012f98b80b72b87c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ks-9330000000-5220625c440a0e4d0e1a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00ks-9330000000-da413d79b085b05c74fa2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000j-9410000000-e4934ca5cda48554f8bc2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-00di-0090000000-d74155da6ca6fff432c52017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9560000000-663aa7cea0b521907df12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-006x-9200000000-475c18425c9352988ee12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01bc-9000000000-afcfa162e86332d3cfa22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-9000000000-421f28522574e5fa8eae2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0f6x-9470000000-cfd10935dbbb59770f3f2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0090000000-460a4bec2421708c0e182017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-2190000000-6eec23d0d7031fc1e28b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dl-9460000000-a6391c9eace085a7cd682017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-006x-9450000000-f677ff82e7d7f3f58ba12017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fe0-9230000000-5d3b471f56b2c2e5535b2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-9200000000-12b30ec690e561fbee152016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9000000000-167b8eb76324b5c3850a2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3790000000-e2e626db270df267d7db2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fki-7910000000-01cff3f952409e9e95502016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9200000000-a56f834482e2844f69242016-08-03View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not Available2021-09-29View Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not Available2018-05-25View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2018-05-25View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected but not QuantifiedNot Applicable details
Detected and Quantified16 uM details
Detected and Quantified16 uM details
Detected and Quantified16 uM details
Detected and Quantified16 uM details
Detected and Quantified16 uM details
Detected and Quantified16 uM details
Detected and Quantified16 uM details
Detected and Quantified16 uM details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected and Quantified15 uM
  • Park, Y. W; Juáre...
 details
Detected and Quantified11 +/- 1 uM details
Detected and Quantified13 +/- 1 uM details
Detected and Quantified11.2 +/- 0.5 uM details
Detected and Quantified12 +/- 3 uM details
Detected and Quantified20.3 +/- 0.3 uM details
Detected and Quantified20 +/- 1 uM details
Detected and Quantified20 +/- 1 uM details
Detected and Quantified20.3 +/- 0.2 uM details
HMDB IDHMDB0000210
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030151
KNApSAcK IDC00001550
Chemspider ID6361
KEGG Compound IDC00864
BioCyc IDPANTOTHENATE
BiGG IDNot Available
Wikipedia LinkPantothenic_Acid
METLIN IDNot Available
PubChem Compound6613
PDB IDNot Available
ChEBI ID46905
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. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  3. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
  4. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  5. Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W. (2007). Park, Y. W; Juárez, Manuela ; Ramos, M.; Haenlein, G. F. W.. Physico-chemical characteristics of goat and sheep milk. Small Ruminant Res.(2007) 68:88-113 doi: 10.1016/j.smallrumres.2006.09.013. Small Ruminant Research.
  6. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  7. Fooddata+, The Technical University of Denmark (DTU) [Link]