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Human Metabolome Database Version 2.5

 

Showing metabocard for Pantothenol (HMDB04231)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2006-08-13 15:54:10
Update Date 2010-07-13 11:27:43
Accession Number HMDB04231
Secondary Accession Numbers Not Available
Common Name Pantothenol
Description In 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.
Synonyms
  1. (+)-Panthenol
  2. (+-)-Pantothenyl alcohol
  3. (R)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
  4. 2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutanamide
  5. Alcool DL-pantotenilico
  6. Alcopan-250
  7. Bepanthen
  8. Bepanthene
  9. Bepantol
  10. D(+)-Panthenol
  11. D(+)-Pantothenyl alcohol
  12. D-(+)-2,4-Dihydroxy-N-(3-hydroxypropyl)-3,3-dimethylbutyramide
  13. D-(+)-Panthenol
  14. D-(+)-Pantothenyl alcohol
  15. D-P-A Injection
  16. D-Panthenol
  17. D-Panthenol 50
  18. DL-Pantothenol
  19. Dexpantenol
  20. Dexpanthenol
  21. Dexpanthenolum
  22. Dextro pantothenyl alcohol
  23. Fancol DL
  24. Ilopan
  25. Intrapan
  26. Motilyn
  27. N-Pantoyl-3-propanolamine
  28. N-Pantoyl-propanolamine
  29. Panadon
  30. Pantenol
  31. Pantenolo
  32. Pantenyl
  33. Panthenolum
  34. Panthoderm
  35. Pantol
  36. Pantothenyl alcohol
  37. Pantothenylol
  38. Penthenol
  39. Provitamin B
  40. Provitamin B5
  41. Synapan
  42. Thenalton
  43. Urupan
  44. Varitan
  45. Zentinic
  46. compnent of ilopan-Choline
  47. d-Pantothenol
  48. d-Pantothenyl alcohol
  49. dl-Panthenol
  50. dl-Pantothenyl alcohol
Chemical IUPAC Name 2,4-dihydroxy-N-(3-hydroxypropyl)-3,3-dimethyl-butanamide
Chemical Formula C9H19NO4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Alcohols
Class
  • Amino Alcohols
  • Amino Acids
Sub Class
  • Miscellaneous amino alcohols
Family
  • Mammalian Metabolite
Species
  • primary alcohol
  • secondary alcohol
  • secondary carboxylic acid amide
Biofunction
  • Enzyme cofactor
Application
—
Source
  • Endogenous
Average Molecular Weight 205.251
Monoisotopic Molecular Weight 205.131409
Isomeric SMILES CC(C)(CO)C(O)C(=O)NCCCO
Canonical SMILES CC(C)(CO)C(O)C(=O)NCCCO
KEGG Compound ID C05944 Link Image
BioCyc ID PANTOTHENOL Link Image
BiGG ID Not Available
Wikipedia Link Dexpanthenol Link Image
NuGOwiki Link HMDB04231 Link Image
Metagene Link HMDB04231 Link Image
METLIN ID 7032 Link Image
PubChem Compound 4678 Link Image
PubChem Substance 8152874 Link Image
ChEBI ID Not Available
CAS Registry Number 81-13-0
InChI Identifier InChI=1/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)
Synthesis Reference Sun, Zhihao; Guo, Xinfu; Wang, Jun. Preparation of D-pantothenol by microbial enzyme method. Faming Zhuanli Shenqing Gongkai Shuomingshu (2002), 6 pp.
Melting Point (Experimental) < 25 oC
Experimental Water Solubility 1000 mg/mL [MERCK INDEX (1996)] Source: PhysProp
Predicted Water Solubility 121.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -1.00 [Predicted by ALOGPS]; -1.2 [Predicted by PubChem via XLOGP]; -1.92 [MEYLAN,WM & HOWARD,PH (1995)] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm (Predicted from LogP)
Biofluid Location Not Available
Tissue Location
Tissue References
Stratum Corneum —
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Pantothenate and CoA Biosynthesis SMP00027 Link Image map00770 Link Image
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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]
  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. [PubMed Link Image]
  5. Wikipedia Link Image