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Identification
NamePantothenic acid
Accession NumberDB01783  (EXPT02501)
TypeSmall Molecule
GroupsNutraceutical
Description

Pantothenic acid, also called pantothenate or vitamin B5 (a B vitamin), is a water-soluble vitamin discovered by Roger J. Williams in 1919. For many animals, pantothenic acid is an essential nutrient. Animals require pantothenic acid to synthesize coenzyme-A (CoA), as well as to synthesize and metabolize proteins, carbohydrates, and fats.
Pantothenic acid is the amide between pantoic acid and β-alanine. Small quantities of pantothenic acid are found in nearly every food, with high amounts in whole-grain cereals, legumes, eggs, meat, royal jelly, avocado, and yogurt. It is commonly found as its alcohol analog, the provitamin panthenol, and as calcium pantothenate. Pantothenic acid is an ingredient in some hair and skin care products. Only the dextrorotatory (D) isomer of pantothenic acid possesses biologic activity. The levorotatory (L) form may antagonize the effects of the dextrorotatory isomer. [Wikipedia]

Structure
Thumb
Synonyms
SynonymLanguageCode
(+)-Pantothenic acidNot AvailableNot Available
D-pantothenic acidNot AvailableNot Available
PantothenateNot AvailableNot Available
Vitamin B5Not AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Calcium pantothenate
137-08-6
Thumb
  • InChI Key: FAPWYRCQGJNNSJ-UBKPKTQASA-L
  • Monoisotopic Mass: 476.168286409
  • Average Mass: 476.532
DBSALT000034
Categories
CAS number79-83-4
WeightAverage: 219.235
Monoisotopic: 219.110672659
Chemical FormulaC9H17NO5
InChI KeyGHOKWGTUZJEAQD-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)
IUPAC Name
3-(2,4-dihydroxy-3,3-dimethylbutanamido)propanoic acid
SMILES
CC(C)(CO)C(O)C(=O)NCCC(O)=O
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentBeta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Fatty acyl
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationStudied for the treatment of many uses such as treatment of testicular torsion, diabetic ulceration, wound healing, acne, obesity, diabetic peripheral polyneuropathy. It has also been investigated for its hypolipidemic effects and as cholesterol lowering agent.
PharmacodynamicsPantothenic acid is used in the synthesis of coenzyme A (CoA). Coenzyme A may act as an acyl group carrier to form acetyl-CoA and other related compounds; this is a way to transport carbon atoms within the cell. CoA is important in energy metabolism for pyruvate to enter the tricarboxylic acid cycle (TCA cycle) as acetyl-CoA, and for α-ketoglutarate to be transformed to succinyl-CoA in the cycle. CoA is also important in the biosynthesis of many important compounds such as fatty acids, cholesterol, and acetylcholine. CoA is incidentally also required in the formation of ACP, which is also required for fatty acid synthesis in addition to CoA. Pantothenic acid in the form of CoA is also required for acylation and acetylation, which, for example, are involved in signal transduction and enzyme activation and deactivation, respectively. Since pantothenic acid participates in a wide array of key biological roles, it is essential to all forms of life. As such, deficiencies in pantothenic acid may have numerous wide-ranging effects, as discussed below.
Mechanism of actionPantothenic acid is incorporated into COENZYME A and protects cells against peroxidative damage by increasing the level of GLUTATHIONE.
AbsorptionWhen found in foods, most pantothenic acid is in the form of CoA or acyl carrier protein (ACP). For the intestinal cells to absorb this vitamin, it must be converted into free pantothenic acid. Within the lumen of the intestine, CoA and ACP are hydrolyzed into 4'-phosphopantetheine. The 4'-phosphopantetheine is then dephosphorylated into pantetheine. Pantetheinase, an intestinal enzyme, then hydrolyzes pantetheine into free pantothenic acid. Free pantothenic acid is absorbed into intestinal cells via a saturable, sodium-dependent active transport system. At high levels of intake, when this mechanism is saturated, some pantothenic acid may also be absorbed via passive diffusion. As intake increases 10-fold, however, absorption rate decreases to 10%. [Wikipedia]
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNo Tolerable Upper Level Intake (UL) has been established for the vitamin.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Pantothenate and CoA BiosynthesisMetabolicSMP00027
Ureidopropionase deficiencyDiseaseSMP00492
Beta-Alanine MetabolismMetabolicSMP00007
Carnosinuria, carnosinemiaDiseaseSMP00493
GABA-Transaminase DeficiencyDiseaseSMP00351
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6189
Blood Brain Barrier+0.6889
Caco-2 permeable-0.7055
P-glycoprotein substrateSubstrate0.5464
P-glycoprotein inhibitor INon-inhibitor0.836
P-glycoprotein inhibitor IINon-inhibitor0.9184
Renal organic cation transporterNon-inhibitor0.95
CYP450 2C9 substrateNon-substrate0.8235
CYP450 2D6 substrateNon-substrate0.8051
CYP450 3A4 substrateNon-substrate0.5411
CYP450 1A2 substrateNon-inhibitor0.9133
CYP450 2C9 substrateNon-inhibitor0.9137
CYP450 2D6 substrateNon-inhibitor0.9417
CYP450 2C19 substrateNon-inhibitor0.8929
CYP450 3A4 substrateNon-inhibitor0.9587
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9305
Ames testNon AMES toxic0.9278
CarcinogenicityNon-carcinogens0.9062
BiodegradationReady biodegradable0.662
Rat acute toxicity1.7394 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9968
hERG inhibition (predictor II)Non-inhibitor0.944
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point195ºC (D-Calcium Pantothenate salt)MSDS
water solubilitySolubleMSDS
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
Spectra
Mass Spec (NIST)Not Available
SpectraMS/MS1D NMR2D NMR
References
Synthesis Reference

John F. Verbeeck, “Process for the production of the calcium salt of pantothenic acid.” U.S. Patent US3935256, issued February, 1971.

US3935256
General Reference
  1. Trumbo, P. R. (2006). “Pantothenic Acid”. In Shils, M. E.; Shike, M.; Ross, A. C. et al.. Modern Nutrition in Health and Disease (10th ed.). Philadelphia, PA: Lippincott Williams & Wilkins. pp. 462–467. ISBN 0-7817-4133-5.
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSDownload (47.9 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Pantothenate kinase

Kind: protein

Organism: Escherichia coli (strain K12)

Pharmacological action: unknown

Components

Name UniProt ID Details
Pantothenate kinase P0A6I3 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:16