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Record Information
Version3.6
Creation Date2006-08-13 14:54:10 UTC
Update Date2016-02-11 01:06:38 UTC
HMDB IDHMDB04231
Secondary Accession NumbersNone
Metabolite Identification
Common NamePantothenol
DescriptionIn cosmetics, panthenol is a humectant, emollient and moisturizer. It binds to hair follicles readily and is a frequent component of shampoos and hair conditioners (in concentrations of 0.1-1%). It coats the hair and seals its surface, lubricating follicles and making strands appear shiny. Panthenol is the alcohol analog of pantothenic acid (vitamin B5), and is thus the provitamin of B5. In organisms it is quickly oxidized to pantothenate. Panthenol is a viscous transparent liquid at room temperature, but salts of pantothenic acid (for example sodium pantothenate) are powders (typically white). It is well soluble in water, alcohol and propylene glycol, soluble in ether and chloroform, and slightly soluble in glycerin.
Structure
Thumb
Synonyms
ValueSource
DL-PanthenolKegg
(+)-PanthenolHMDB
(+-)-Pantothenyl alcoholHMDB
(R)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamideHMDB
Alcool DL-pantotenilicoHMDB
Alcopan-250HMDB
BepanthenHMDB
BepantheneHMDB
BepantolHMDB
Compnent OF ilopan-cholineHMDB
D(+)-PanthenolHMDB
D(+)-Pantothenyl alcoholHMDB
D-(+)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramideHMDB
D-(+)-PanthenolHMDB
D-(+)-Pantothenyl alcoholHMDB
D-P-a InjectionHMDB
D-PanthenolHMDB
D-Panthenol 50HMDB
D-PantothenolHMDB
D-Pantothenyl alcoholHMDB
DexpantenolHMDB
DexpanthenolHMDB
DexpanthenolumHMDB
dextro Pantothenyl alcoholHMDB
DL-PantothenolHMDB
DL-Pantothenyl alcoholHMDB
Fancol DLHMDB
IlopanHMDB
IntrapanHMDB
MotilynHMDB
N-Pantoyl-3-propanolamineHMDB
N-Pantoyl-propanolamineHMDB
PanadonHMDB
PantenolHMDB
PantenoloHMDB
PantenylHMDB
PanthenolumHMDB
PanthodermHMDB
PantolHMDB
Pantothenyl alcoholHMDB
PantothenylolHMDB
PenthenolHMDB
Provitamin bHMDB
Provitamin b5HMDB
SynapanHMDB
ThenaltonHMDB
UrupanHMDB
VaritanHMDB
ZentinicHMDB
Chemical FormulaC9H19NO4
Average Molecular Weight205.2515
Monoisotopic Molecular Weight205.131408101
IUPAC Name2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
Traditional Namepanthenol
CAS Registry Number81-13-0
SMILES
CC(C)(CO)C(O)C(=O)NCCCO
InChI Identifier
InChI=1S/C9H19NO4/c1-9(2,6-12)7(13)8(14)10-4-3-5-11/h7,11-13H,3-6H2,1-2H3,(H,10,14)
InChI KeyInChIKey=SNPLKNRPJHDVJA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl amines. These are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty amides
Direct ParentN-acyl amines
Alternative Parents
Substituents
  • N-acyl-amine
  • Monosaccharide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Alkanolamine
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
Biofunction
  • Enzyme cofactor
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility121.0 mg/mLALOGPS
logP-1ALOGPS
logP-1.7ChemAxon
logS-0.23ALOGPS
pKa (Strongest Acidic)12.69ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area89.79 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity51.88 m3·mol-1ChemAxon
Polarizability21.87 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations
  • Saliva
Tissue Location
  • Stratum Corneum
Pathways
NameSMPDB LinkKEGG Link
Pantothenate and CoA BiosynthesisSMP00027map00770
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008430
KNApSAcK IDNot Available
Chemspider ID4516
KEGG Compound IDC05944
BioCyc IDPANTOTHENOL
BiGG IDNot Available
Wikipedia LinkDexpanthenol
NuGOwiki LinkHMDB04231
Metagene LinkHMDB04231
METLIN ID7032
PubChem Compound4678
PDB IDNot Available
ChEBI ID895821
References
Synthesis ReferenceSun, Zhihao; Guo, Xinfu; Wang, Jun. Preparation of D-pantothenol by microbial enzyme method. Faming Zhuanli Shenqing Gongkai Shuomingshu (2002), 6 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Gobbels M, Gross D: [Clinical study of the effectiveness of a dexpanthenol containing artificial tears solution (Siccaprotect) in treatment of dry eyes] Klin Monatsbl Augenheilkd. 1996 Aug-Sep;209(2-3):84-8. [8992089 ]
  2. Gehring W, Gloor M: Effect of topically applied dexpanthenol on epidermal barrier function and stratum corneum hydration. Results of a human in vivo study. Arzneimittelforschung. 2000 Jul;50(7):659-63. [10965426 ]
  3. Sachs M, Asskali F, Lanaras C, Forster H, Bockhorn H: [The metabolism of panthenol in patients with postoperative intestinal atony] Z Ernahrungswiss. 1990 Dec;29(4):270-83. [2080639 ]
  4. Ebner F, Heller A, Rippke F, Tausch I: Topical use of dexpanthenol in skin disorders. Am J Clin Dermatol. 2002;3(6):427-33. [12113650 ]