Human Metabolome Database Version 3.5

Showing metabocard for Octanol (HMDB01183)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:30:40 -0600
HMDB ID HMDB01183
Secondary Accession Numbers None
Metabolite Identification
Common Name Octanol
Description Octanol occurs naturally in the form of esters in some essential oils. Octanol and water are immiscible. The distribution of a compound between water and octanol is used to calculate the partition coefficient (logP) of that molecule. Water/octanol partitioning is a good approximation of the partitioning between the cytosol and lipid membranes of living systems.(wikipedia). A colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed). It is also one of many compounds derived from tobacco and tobacco smoke and shown to increase the permeability of the membranes of human lung fibroblasts (PMID 7466833 Link_out).
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Hydroxyoctane
  2. 1-Octanol
  3. 2-Capryl alcohol
  4. 2-Octanol
  5. 2-Octanol ~99%
  6. Alcohol C-8
  7. Alfol 8
  8. Capryl alcohol
  9. Caprylic alcohol
  10. DL-2-Octanol
  11. Dytol m-83
  12. Emery 3322
  13. Emery 3324
  14. Epal 8
  15. Heptyl carbinol
  16. Hexyl methyl carbinol
  17. Lorol 20
  18. Lorol C8
  19. N-Heptyl carbinol
  20. N-Octan-1-ol
  21. N-Octanol
  22. N-Octyl alcohol
  23. N-Octyl-alcohol
  24. Octan-1-ol
  25. Octan-2-ol
  26. Octan-2-ol 98+ %
  27. Octanol
  28. Octilin
  29. Octyl alcohol
  30. Octyl alcohol normal-primary
  31. Octyl-alcohol
  32. Prim-N-octyl alcohol
  33. Primary octyl alcohol
  34. Sipol L8
Chemical Formula C8H18O
Average Molecular Weight 130.2279
Monoisotopic Molecular Weight 130.135765198
IUPAC Name octan-1-ol
Traditional IUPAC Name octanol
CAS Registry Number 111-87-5
SMILES CCCCCCCCO
InChI Identifier InChI=1S/C8H18O/c1-2-3-4-5-6-7-8-9/h9H,2-8H2,1H3
InChI Key KBPLFHHGFOOTCA-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Alcohols
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Fatty alcohols(Lipidmaps)
  • a small molecule(Cyc)
  • octanol(ChEBI)
  • primary alcohol(ChEBI)
Substituents
  • Primary Alcohol
Direct Parent Fatty Alcohols
Ontology
Status Detected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Component of Fatty acid metabolism
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -15.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 0.54 mg/mL Not Available
LogP 3.00 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 0.53 g/L ALOGPS
LogP 3.21 ALOGPS
LogP 2.58 ChemAxon
LogS -2.39 ALOGPS
pKa (strongest acidic) 16.84 ChemAxon
pKa (strongest basic) -2 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 6 ChemAxon
Refractivity 40.54 ChemAxon
Polarizability 17.42 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum EI-B (HITACHI RMU-6M)
MS/MS Spectrum EI-B (HITACHI RMU-7M)
MS/MS Spectrum EI-B (HITACHI M-80)
MS/MS Spectrum CI-B (HITACHI M-80)
MS/MS Spectrum EI-B (HITACHI M-80B)
MS/MS Spectrum EI-B (SHIMADZU QP-1000)
MS/MS Spectrum GC-MS
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Urine
Tissue Location
  • Muscle
  • Fibroblasts
  • Intestine
  • Placenta
  • Brain
  • Skin
  • Adipose Tissue
  • Stratum Corneum
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Breast cancer
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB012583
KNApSAcK ID C00001264 Link_out
Chemspider ID 932 Link_out
KEGG Compound ID C00756 Link_out
BioCyc ID OCTANOL Link_out
BiGG ID Not Available
Wikipedia Link Octanol Link_out
NuGOwiki Link HMDB01183 Link_out
Metagene Link HMDB01183 Link_out
METLIN ID 6063 Link_out
PubChem Compound 957 Link_out
PDB ID OC9 Link_out
ChEBI ID 16188 Link_out
References
Synthesis Reference Hagiwara, Nobue; Takahashi, Shigetoshi; Shibano, Toshishige. n-Octanol. Jpn. Tokkyo Koho (1977), 3 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Fujioka H, Murase K, Inoue T, Ishimaru Y, Akamune A, Yamamoto Y, Ikezoe J: A method for estimating the integral of the input function for the quantification of cerebral blood flow with 123I-IMP using one-point arterial blood sampling. Nucl Med Commun. 1998 Jun;19(6):561-6. Pubmed: 10234660 Link_out
  2. Tuntland T, Odinecs A, Pereira CM, Nosbisch C, Unadkat JD: In vitro models to predict the in vivo mechanism, rate, and extent of placental transfer of dideoxynucleoside drugs against human immunodeficiency virus. Am J Obstet Gynecol. 1999 Jan;180(1 Pt 1):198-206. Pubmed: 9914604 Link_out
  3. Okazawa H, Yonekura Y, Fujibayashi Y, Nishizawa S, Magata Y, Ishizu K, Tanaka F, Tsuchida T, Tamaki N, Konishi J: Clinical application and quantitative evaluation of generator-produced copper-62-PTSM as a brain perfusion tracer for PET. J Nucl Med. 1994 Dec;35(12):1910-5. Pubmed: 7989968 Link_out
  4. Anderson BD, Raykar PV: Solute structure-permeability relationships in human stratum corneum. J Invest Dermatol. 1989 Aug;93(2):280-6. Pubmed: 2754277 Link_out
  5. Bunge AL, Cleek RL: A new method for estimating dermal absorption from chemical exposure: 2. Effect of molecular weight and octanol-water partitioning. Pharm Res. 1995 Jan;12(1):88-95. Pubmed: 7724493 Link_out
  6. Potts RO, Guy RH: Predicting skin permeability. Pharm Res. 1992 May;9(5):663-9. Pubmed: 1608900 Link_out
  7. Poulin P, Schoenlein K, Theil FP: Prediction of adipose tissue: plasma partition coefficients for structurally unrelated drugs. J Pharm Sci. 2001 Apr;90(4):436-47. Pubmed: 11170034 Link_out
  8. Southwell D, Barry BW: Penetration enhancers for human skin: mode of action of 2-pyrrolidone and dimethylformamide on partition and diffusion of model compounds water, n-alcohols, and caffeine. J Invest Dermatol. 1983 Jun;80(6):507-14. Pubmed: 6854051 Link_out
  9. Barry BW, Bennett SL: Effect of penetration enhancers on the permeation of mannitol, hydrocortisone and progesterone through human skin. J Pharm Pharmacol. 1987 Jul;39(7):535-46. Pubmed: 2886623 Link_out
  10. Fujioka H, Murase K, Inoue T, Ishimaru Y, Ebara H, Akamune A, Yamamoto Y, Mochizuki T, Ikezoe J: [Estimation of integral of input function for quantification of cerebral blood flow with N-isopropyl-p-[123I]iodoamphetamine using one-point venous blood sampling] Kaku Igaku. 1999 Oct;36(8):801-7. Pubmed: 10586540 Link_out
  11. Ross1 JS, Shah JC: Reduction in skin permeation of N,N-diethyl-m-toluamide (DEET) by altering the skin/vehicle partition coefficient. J Control Release. 2000 Jul 3;67(2-3):211-21. Pubmed: 10825555 Link_out
  12. Hadgraft J, Goosen C, du Plessis J, Flynn G: Predicting the dermal absorption of thalidomide and its derivatives. Skin Pharmacol Appl Skin Physiol. 2003 Mar-Apr;16(2):123-9. Pubmed: 12637788 Link_out
  13. Al-Madhoun AS, Johnsamuel J, Barth RF, Tjarks W, Eriksson S: Evaluation of human thymidine kinase 1 substrates as new candidates for boron neutron capture therapy. Cancer Res. 2004 Sep 1;64(17):6280-6. Pubmed: 15342416 Link_out
  14. Shun-xing L, Nan-sheng D, Feng-ying Z: Effect of digestive site acidity and compatibility on the species, lipopily and bioavailability of iron, manganese and zinc in Prunus persica Batsch and Carthamus tinctorus. Bioorg Med Chem Lett. 2004 Jan 19;14(2):505-10. Pubmed: 14698191 Link_out
  15. Geyer H, Scheunert I, Korte F: Bioconcentration potential of organic environmental chemicals in humans. Regul Toxicol Pharmacol. 1986 Dec;6(4):313-47. Pubmed: 3101145 Link_out
  16. Lange Y, Ye J, Steck TL: Activation of membrane cholesterol by displacement from phospholipids. J Biol Chem. 2005 Oct 28;280(43):36126-31. Epub 2005 Aug 29. Pubmed: 16129675 Link_out
  17. Mantione KJ, Goumon Y, Esch T, Stefano GB: Morphine 6beta glucuronide: fortuitous morphine metabolite or preferred peripheral regulatory opiate? Med Sci Monit. 2005 May;11(5):MS43-46. Epub 2005 Apr 28. Pubmed: 15874899 Link_out
  18. Stafford RG, Mehta M, Kemppainen BW: Comparison of the partition coefficient and skin penetration of a marine algal toxin (lyngbyatoxin A). Food Chem Toxicol. 1992 Sep;30(9):795-801. Pubmed: 1427518 Link_out
  19. Makino K, Masuda Y, Gotoh S: [Measurement of regional cerebral blood flow using one-point arterial blood sampling and microsphere model with 123I-IMP: correction of one-point arterial sampling count by whole brain count ratio] Kaku Igaku. 1998 Jul;35(6):405-12. Pubmed: 9753919 Link_out
  20. Zuo Y, Yeh JZ, Narahashi T: Octanol modulation of neuronal nicotinic acetylcholine receptor single channels. Alcohol Clin Exp Res. 2004 Nov;28(11):1648-56. Pubmed: 15547451 Link_out
  21. Thelestam M, Curvall M, Enzell CR: Effect of tobacco smoke compounds on the plasma membrane of cultured human lung fibroblasts. Toxicology. 1980;15(3):203-17. Pubmed: 7466833 Link_out

Enzymes
Name: Cytochrome P450 4A11
Reactions:
Octane + reduced rubredoxin + Oxygen unknown Octanol + oxidized rubredoxin + Water details
Gene Name: CYP4A11
Uniprot ID: Q02928 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 4A22
Reactions:
Octane + reduced rubredoxin + Oxygen unknown Octanol + oxidized rubredoxin + Water details
Gene Name: CYP4A22
Uniprot ID: Q5TCH4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA