Human Metabolome Database Version 3.5

Showing metabocard for 1-Butanol (HMDB04327)

Record Information
Version 3.5
Creation Date 2006-08-13 10:50:24 -0600
Update Date 2013-02-08 17:13:11 -0700
HMDB ID HMDB04327
Secondary Accession Numbers None
Metabolite Identification
Common Name 1-Butanol
Description 1-Butanol, which is also known as n-butanol or 1-butanol or butyl alcohol (sometimes also called biobutanol when produced biologically), is an alcohol with a 4 carbon structure and the molecular formula of C4H10O. It is primarily used as a solvent, as an intermediate in chemical synthesis, and as a fuel. There are four isomeric structures for butanol. The straight chain isomer with the alcohol at an internal carbon is sec-butanol or 2-butanol. The branched isomer with the alcohol at a terminal carbon is isobutanol, and the branched isomer with the alcohol at the internal carbon is tert-butanol. 1-Butanol is produced in small amounts by gut microbial fermenetation through the butanoate metabolic pathway.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Butanol
  2. 1-Butyl alcohol
  3. Butanol
  4. Butyl alcohol
  5. Butyl hydroxide
  6. Hemostyp
  7. Methylolpropane
  8. N-Butanol
  9. N-Butyl alcohol
  10. Propylcarbinol
Chemical Formula C4H10O
Average Molecular Weight 74.1216
Monoisotopic Molecular Weight 74.073164942
IUPAC Name butan-1-ol
Traditional IUPAC Name butan-1-ol
CAS Registry Number 71-36-3
SMILES CCCCO
InChI Identifier InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3
InChI Key LRHPLDYGYMQRHN-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Alcohols and Polyols
Sub Class Primary Alcohols
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Fatty alcohols(Lipidmaps)
  • a primary alcohol(Cyc)
  • alkyl alcohol(ChEBI)
  • primary alcohol(ChEBI)
Substituents
  • N/A
Direct Parent Primary Alcohols
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point -89.8 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 63.2 mg/mL at 25 °C Not Available
LogP 0.88 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 158 g/L ALOGPS
LogP 0.84 ALOGPS
LogP 0.81 ChemAxon
LogS 0.33 ALOGPS
pKa (strongest acidic) 16.95 ChemAxon
pKa (strongest basic) -1.9 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 22.13 ChemAxon
Polarizability 9.21 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-80B)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations Not Available
Biofluid Locations
  • Blood
Tissue Location
  • Fibroblasts
  • Pancreas
  • Kidney
  • Liver
  • Epidermis
  • Spleen
  • Stratum Corneum
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.08 (0.00 - 0.27) uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified 0.11 (0 - 2.43) uM Adult (>18 years old) Both Diabetes
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  • Liebich HM, Buelow HJ, Kallmayer R: Quantification of endogenous aliphatic alcohols in serum and urine. J Chromatogr. 1982 Apr 30;239:343-9. Pubmed: 7096503 Link_out
      Associated OMIM IDs
      • 125853 Link_out (Diabetes mellitus type 2)
      DrugBank ID DB02145 Link_out
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB012614
      KNApSAcK ID C00035814 Link_out
      Chemspider ID 258 Link_out
      KEGG Compound ID C06142 Link_out
      BioCyc ID BUTANOL Link_out
      BiGG ID Not Available
      Wikipedia Link 1-Butanol Link_out
      NuGOwiki Link HMDB04327 Link_out
      Metagene Link HMDB04327 Link_out
      METLIN ID 7052 Link_out
      PubChem Compound 263 Link_out
      PDB ID 1BO Link_out
      ChEBI ID 28885 Link_out
      References
      Synthesis Reference Tsuchida, Takashi; Sakuma, Shuji. Ethanol to 1-butanol on hydroxyapatite. Shokubai (2007), 49(3), 238-243.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Copovi A, Diez-Sales O, Herraez-Dominguez JV, Herraez-Dominguez M: Enhancing effect of alpha-hydroxyacids on "in vitro" permeation across the human skin of compounds with different lipophilicity. Int J Pharm. 2006 May 11;314(1):31-6. Epub 2006 Mar 20. Pubmed: 16545927 Link_out
      2. Bailyes EM, Seabrook RN, Calvin J, Maguire GA, Price CP, Siddle K, Luzio JP: The preparation of monoclonal antibodies to human bone and liver alkaline phosphatase and their use in immunoaffinity purification and in studying these enzymes when present in serum. Biochem J. 1987 Jun 15;244(3):725-33. Pubmed: 2451502 Link_out
      3. Gainer AL, Stinson RA: Evidence that alkaline phosphatase from human neutrophils is the same gene product as the liver/kidney/bone isoenzyme. Clin Chim Acta. 1982 Aug 4;123(1-2):11-7. Pubmed: 7116633 Link_out
      4. Yamamoto K, Takahashi Y, Mano T, Sakata Y, Nishikawa N, Yoshida J, Oishi Y, Hori M, Miwa T, Inoue S, Masuyama T: N-methylethanolamine attenuates cardiac fibrosis and improves diastolic function: inhibition of phospholipase D as a possible mechanism. Eur Heart J. 2004 Jul;25(14):1221-9. Pubmed: 15246640 Link_out
      5. Seiffert UB, Siede WH, Welsch GJ, Oremek G: Multiple forms of alkaline phosphatases in human liver tissue. Clin Chim Acta. 1984 Dec 15;144(1):17-27. Pubmed: 6210164 Link_out
      6. Chen M: Amended final report of the safety assessment of t-Butyl Alcohol as used in cosmetics. Int J Toxicol. 2005;24 Suppl 2:1-20. Pubmed: 16154913 Link_out
      7. Okamoto M, Kaji R, Kasetani H, Yoshida H, Moriya Y, Saito M, Sato M: Purification and characterization of interferon-gamma-inducing molecule of OK-432, a penicillin-killed streptococcal preparation, by monoclonal antibody neutralizing interferon-gamma-inducing activity of OK-432. J Immunother. 1993 May 4;13(4):232-42. Pubmed: 8334107 Link_out
      8. Chang CH, Angellis D: Identification of a butanol-extractable human placenta-specific antigen with alkaline phosphatase activity. J Immunol. 1976 Jul;117(1):91-6. Pubmed: 58937 Link_out
      9. Oakley DM, Swarbrick J: Effects of ionization on the percutaneous absorption of drugs: partitioning of nicotine into organic liquids and hydrated stratum corneum. J Pharm Sci. 1987 Dec;76(12):866-71. Pubmed: 3440928 Link_out
      10. Waddell WJ, Marlowe C: Inhibition by alcohols of the localization of radioactive nitrosonornicotine in sites of tumor formation. Science. 1983 Jul 1;221(4605):51-3. Pubmed: 6857261 Link_out
      11. Bieler CA, Cornelius MG, Klein R, Arlt VM, Wiessler M, Phillips DH, Schmeiser HH: DNA adduct formation by the environmental contaminant 3-nitrobenzanthrone after intratracheal instillation in rats. Int J Cancer. 2005 Oct 10;116(6):833-8. Pubmed: 15856450 Link_out
      12. Wulkan RW, Huijskes-Heins MI, Leijnse B: Hydrophobic properties of alkaline phosphatases. Int J Biochem. 1986;18(11):1045-51. Pubmed: 3803695 Link_out
      13. Kalimanovska V, Whitaker KB, Moss DW: Effect of bromelain on alkaline phosphatases of intestinal and non-intestinal tissues and serum. Clin Chim Acta. 1987 Dec;170(2-3):219-25. Pubmed: 3436056 Link_out
      14. Basu A, Glew RH: Characterization of the activation of rat liver beta-glucosidase by sialosylgangliotetraosylceramide. J Biol Chem. 1985 Oct 25;260(24):13067-73. Pubmed: 3932339 Link_out
      15. Arlt VM, Sorg BL, Osborne M, Hewer A, Seidel A, Schmeiser HH, Phillips DH: DNA adduct formation by the ubiquitous environmental pollutant 3-nitrobenzanthrone and its metabolites in rats. Biochem Biophys Res Commun. 2003 Jan 3;300(1):107-14. Pubmed: 12480528 Link_out

      Enzymes
      Name: Serum paraoxonase/lactonase 3
      Reactions: Not Available
      Gene Name: PON3
      Uniprot ID: Q15166 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Serum paraoxonase/arylesterase 1
      Reactions: Not Available
      Gene Name: PON1
      Uniprot ID: P27169 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Serum paraoxonase/arylesterase 2
      Reactions: Not Available
      Gene Name: PON2
      Uniprot ID: Q15165 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Intestinal-type alkaline phosphatase
      Reactions: Not Available
      Gene Name: ALPI
      Uniprot ID: P09923 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Lysosomal acid phosphatase
      Reactions: Not Available
      Gene Name: ACP2
      Uniprot ID: P11117 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alkaline phosphatase, tissue-nonspecific isozyme
      Reactions: Not Available
      Gene Name: ALPL
      Uniprot ID: P05186 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Tartrate-resistant acid phosphatase type 5
      Reactions: Not Available
      Gene Name: ACP5
      Uniprot ID: P13686 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alkaline phosphatase, placental-like
      Reactions: Not Available
      Gene Name: ALPPL2
      Uniprot ID: P10696 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Aldehyde dehydrogenase X, mitochondrial
      Reactions: Not Available
      Gene Name: ALDH1B1
      Uniprot ID: P30837 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Sulfotransferase family cytosolic 2B member 1
      Reactions: Not Available
      Gene Name: SULT2B1
      Uniprot ID: O00204 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Sorbitol dehydrogenase
      Reactions: Not Available
      Gene Name: SORD
      Uniprot ID: Q00796 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alcohol dehydrogenase [NADP(+)]
      Reactions: Not Available
      Gene Name: AKR1A1
      Uniprot ID: P14550 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alcohol dehydrogenase 4
      Reactions: Not Available
      Gene Name: ADH4
      Uniprot ID: P08319 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alcohol dehydrogenase 1B
      Reactions: Not Available
      Gene Name: ADH1B
      Uniprot ID: P00325 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alcohol dehydrogenase 1A
      Reactions: Not Available
      Gene Name: ADH1A
      Uniprot ID: P07327 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Alcohol dehydrogenase 6
      Reactions: Not Available
      Gene Name: ADH6
      Uniprot ID: P28332 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Beta-glucuronidase
      Reactions: Not Available
      Gene Name: GUSB
      Uniprot ID: P08236 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Plasma alpha-L-fucosidase
      Reactions: Not Available
      Gene Name: FUCA2
      Uniprot ID: Q9BTY2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Trans-2-enoyl-CoA reductase, mitochondrial
      Reactions: Not Available
      Gene Name: MECR
      Uniprot ID: Q9BV79 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Lecithin retinol acyltransferase
      Reactions: Not Available
      Gene Name: LRAT
      Uniprot ID: O95237 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Nuclear receptor subfamily 1 group I member 3
      Reactions: Not Available
      Gene Name: NR1I3
      Uniprot ID: Q14994 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Zinc-binding alcohol dehydrogenase domain-containing protein 2
      Reactions: Not Available
      Gene Name: ZADH2
      Uniprot ID: Q8N4Q0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Retinol dehydrogenase 13
      Reactions: Not Available
      Gene Name: RDH13
      Uniprot ID: Q8NBN7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Hydroxyacid-oxoacid transhydrogenase, mitochondrial
      Reactions: Not Available
      Gene Name: ADHFE1
      Uniprot ID: Q8IWW8 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Fatty acyl-CoA reductase 2
      Reactions: Not Available
      Gene Name: FAR2
      Uniprot ID: Q96K12 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Acyl-CoA wax alcohol acyltransferase 2
      Reactions: Not Available
      Gene Name: AWAT2
      Uniprot ID: Q6E213 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Klotho
      Reactions: Not Available
      Gene Name: KL
      Uniprot ID: Q9UEF7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Testicular acid phosphatase
      Reactions: Not Available
      Gene Name: ACPT
      Uniprot ID: Q9BZG2 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Carboxylesterase 5A
      Reactions: Not Available
      Gene Name: CES5A
      Uniprot ID: Q6NT32 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Acid phosphatase-like protein 2
      Reactions: Not Available
      Gene Name: ACPL2
      Uniprot ID: Q8TE99 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Synaptic vesicle membrane protein VAT-1 homolog-like
      Reactions: Not Available
      Gene Name: VAT1L
      Uniprot ID: Q9HCJ6 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Quinone oxidoreductase PIG3
      Reactions: Not Available
      Gene Name: TP53I3
      Uniprot ID: Q53FA7 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Synaptic vesicle membrane protein VAT-1 homolog
      Reactions: Not Available
      Gene Name: VAT1
      Uniprot ID: Q99536 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Reticulon-4-interacting protein 1, mitochondrial
      Reactions: Not Available
      Gene Name: RTN4IP1
      Uniprot ID: Q8WWV3 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA