(R)-pantothenate (PAMDB110214)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110214
Identification
Name: (R)-pantothenate
Description:A pantothenate that is the conjugate base of (R)-pantothenic acid, obtained by deprotonation of the carboxy group.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • vitamin B5
  • (R)-pantothenic acid
  • D-pantothenic acid
Chemical Formula: C9H16NO5
Average Molecular Weight: 218.23
Monoisotopic Molecular Weight: 219.1106726614
InChI Key: GHOKWGTUZJEAQD-ZETCQYMHSA-M
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)/p-1/t7-/m0/s1
CAS number: 79-83-4
IUPAC Name:3-[(2R)-2,4-dihydroxy-3,3-dimethylbutanamido]propanoate
Traditional IUPAC Name: DL-pantothenic acid
SMILES:CC(C)(CO)C(O)C(=O)NCCC(=O)[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct Parent Beta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organooxygen compound
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: < 25 °C
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity51.51 m3·mol-1ChemAxon
Polarizability21.92 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
beta-Alanine + (R)-pantoate + ATP → Hydrogen ion + (R)-pantothenate + phosphate + ADP
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-3190000000-7a9e1fb7ca94ff4714e8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00dl-9100000000-ada04a866c6d38235607View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0596-9000000000-aea14dc63426efd5a60dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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. [19212411 ]
  • 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. [2026685 ]
  • 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. [9212762 ]
  • 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. [1011047 ]
  • 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. [10683755 ]
  • 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. [600836 ]
  • Guilarte TR: A radiometric microbiological assay for pantothenic acid in biological fluids. Anal Biochem. 1989 Apr;178(1):63-6. [2499220 ]
  • 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. [7025609 ]
  • Eissenstat BR, Wyse BW, Hansen RG: Pantothenic acid status of adolescents. Am J Clin Nutr. 1986 Dec;44(6):931-7. [3788840 ]
  • 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. [182198 ]
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
CAS79-83-4
ChEBI29032
ChemSpider146912
HMDBHMDB00210
IAF126036234
KEGGC00864
PubChem167945
WikipediaVitamin_B5