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Human Metabolome Database Version 3.5

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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 | 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 Comments
Blood Detected and Quantified
Article_icon
0.08 (0.00 - 0.27) uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
0.11 (0 - 2.43) uM Adult (>18 years old) Both Diabetes Not Available
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
    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:
    • an aryl dialkyl phosphate + H2O = dialkyl phosphate + an aryl alcohol [RN:R03979]
    Gene Name: PON3
    Uniprot ID: Q15166 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Serum paraoxonase/arylesterase 1
    Reactions:
    • an aryl dialkyl phosphate + H2O = dialkyl phosphate + an aryl alcohol [RN:R03979]
    Gene Name: PON1
    Uniprot ID: P27169 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Serum paraoxonase/arylesterase 2
    Reactions:
    • an N-acyl-L-homoserine lactone + H2O = an N-acyl-L-homoserine [RN:R08970]
    Gene Name: PON2
    Uniprot ID: Q15165 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Intestinal-type alkaline phosphatase
    Reactions:
    • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
    Gene Name: ALPI
    Uniprot ID: P09923 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Lysosomal acid phosphatase
    Reactions:
    • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
    Gene Name: ACP2
    Uniprot ID: P11117 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Alkaline phosphatase, tissue-nonspecific isozyme
    Reactions:
    • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
    Gene Name: ALPL
    Uniprot ID: P05186 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Tartrate-resistant acid phosphatase type 5
    Reactions:
    • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
    Gene Name: ACP5
    Uniprot ID: P13686 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Alkaline phosphatase, placental-like
    Reactions:
    • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
    Gene Name: ALPPL2
    Uniprot ID: P10696 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Aldehyde dehydrogenase X, mitochondrial
    Reactions:
    • an aldehyde + NAD+ + H2O = an acid + NADH + H+ [RN:R00538]
    Gene Name: ALDH1B1
    Uniprot ID: P30837 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Sulfotransferase family cytosolic 2B member 1
    Reactions:
    • 3'-phosphoadenylyl sulfate + an alcohol = adenosine 3',5'-bisphosphate + an alkyl sulfate [RN:R00629]
    Gene Name: SULT2B1
    Uniprot ID: O00204 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Sorbitol dehydrogenase
    Reactions:
    • L-iditol + NAD+ = L-sorbose + NADH + H+ [RN:R07145]
    Gene Name: SORD
    Uniprot ID: Q00796 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Alcohol dehydrogenase [NADP+]
    Reactions:
    • an alcohol + NADP+ = an aldehyde + NADPH + H+ [RN:R07328]
    Gene Name: AKR1A1
    Uniprot ID: P14550 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Alcohol dehydrogenase 4
    Reactions:
    • an alcohol + NAD+ = an aldehyde or ketone + NADH + H+ [RN:R07326 R07327]
    Gene Name: ADH4
    Uniprot ID: P08319 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Alcohol dehydrogenase 1B
    Reactions:
    • an alcohol + NAD+ = an aldehyde or ketone + NADH + H+ [RN:R07326 R07327]
    Gene Name: ADH1B
    Uniprot ID: P00325 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Alcohol dehydrogenase 1A
    Reactions:
    • an alcohol + NAD+ = an aldehyde or ketone + NADH + H+ [RN:R07326 R07327]
    Gene Name: ADH1A
    Uniprot ID: P07327 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Alcohol dehydrogenase 6
    Reactions:
    • an alcohol + NAD+ = an aldehyde or ketone + NADH + H+ [RN:R07326 R07327]
    Gene Name: ADH6
    Uniprot ID: P28332 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Beta-glucuronidase
    Reactions:
    • a beta-D-glucuronoside + H2O = D-glucuronate + an alcohol [RN:R01478]
    Gene Name: GUSB
    Uniprot ID: P08236 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Plasma alpha-L-fucosidase
    Reactions:
    • an alpha-L-fucoside + H2O = L-fucose + an alcohol [RN:R03162]
    Gene Name: FUCA2
    Uniprot ID: Q9BTY2 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Trans-2-enoyl-CoA reductase, mitochondrial
    Reactions:
    • acyl-CoA + NADP+ = trans-2,3-dehydroacyl-CoA + NADPH + H+ [RN:R07162]
    Gene Name: MECR
    Uniprot ID: Q9BV79 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Lecithin retinol acyltransferase
    Reactions:
    • phosphatidylcholine + retinol---[cellular-retinol-binding-protein] = 2-acylglycerophosphocholine + retinyl-ester---[cellular-retinol-binding-protein] [RN:R04514]
    Gene Name: LRAT
    Uniprot ID: O95237 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Nuclear receptor subfamily 1 group I member 3
    Reactions:
      Gene Name: NR1I3
      Uniprot ID: Q14994 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Zinc-binding alcohol dehydrogenase domain-containing protein 2
      Reactions:
        Gene Name: ZADH2
        Uniprot ID: Q8N4Q0 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Retinol dehydrogenase 13
        Reactions:
          Gene Name: RDH13
          Uniprot ID: Q8NBN7 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Hydroxyacid-oxoacid transhydrogenase, mitochondrial
          Reactions:
          • (S)-3-hydroxybutanoate + 2-oxoglutarate = acetoacetate + (R)-2-hydroxyglutarate [RN:R03225]
          Gene Name: ADHFE1
          Uniprot ID: Q8IWW8 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Fatty acyl-CoA reductase 2
          Reactions:
            Gene Name: FAR2
            Uniprot ID: Q96K12 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Acyl-CoA wax alcohol acyltransferase 2
            Reactions:
            • acyl-CoA + a long-chain alcohol = CoA + a long-chain ester [RN:R01999]
            Gene Name: AWAT2
            Uniprot ID: Q6E213 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Klotho
            Reactions:
            • a beta-D-glucuronoside + H2O = D-glucuronate + an alcohol [RN:R01478]
            Gene Name: KL
            Uniprot ID: Q9UEF7 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Testicular acid phosphatase
            Reactions:
            • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
            Gene Name: ACPT
            Uniprot ID: Q9BZG2 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Carboxylesterase 7
            Reactions:
            • a carboxylic ester + H2O = an alcohol + a carboxylate [RN:R00630]
            Gene Name: CES7
            Uniprot ID: Q6NT32 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Acid phosphatase-like protein 2
            Reactions:
            • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
            Gene Name: ACPL2
            Uniprot ID: Q8TE99 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Synaptic vesicle membrane protein VAT-1 homolog-like
            Reactions:
              Gene Name: VAT1L
              Uniprot ID: Q9HCJ6 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Quinone oxidoreductase PIG3
              Reactions:
                Gene Name: TP53I3
                Uniprot ID: Q53FA7 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: Synaptic vesicle membrane protein VAT-1 homolog
                Reactions:
                  Gene Name: VAT1
                  Uniprot ID: Q99536 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Reticulon-4-interacting protein 1, mitochondrial
                  Reactions:
                    Gene Name: RTN4IP1
                    Uniprot ID: Q8WWV3 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA