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Human Metabolome Database Version 3.5

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Showing metabocard for Isopropyl alcohol (HMDB00863)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:09:28 -0700
HMDB ID HMDB00863
Secondary Accession Numbers None
Metabolite Identification
Common Name Isopropyl alcohol
Description Isopropyl alcohol or 2-propanol is an isomer of 1-propanol. It is a colorless liquid having disinfectant properties. It is used in the manufacture of acetone and its derivatives and as a solvent. Topically, it is used as an antiseptic. Small amounts of this alcohol are produced naturally by gut microbial flora.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Propanol
  2. 2-Propyl alcohol
  3. Alcojel
  4. Alkolave
  5. Avantin
  6. Avantine
  7. Hartosol
  8. Isopropanol
  9. Isopropyl alcohol
  10. Lavaco
  11. Petrohol
  12. Takineocol
Chemical Formula C3H8O
Average Molecular Weight 60.095
Monoisotopic Molecular Weight 60.057514878
IUPAC Name propan-2-ol
Traditional IUPAC Name isopropyl alcohol
CAS Registry Number 67-63-0
SMILES CC(C)O
InChI Identifier InChI=1S/C3H8O/c1-3(2)4/h3-4H,1-2H3
InChI Key KFZMGEQAYNKOFK-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Alcohols and Polyols
Sub Class Secondary Alcohols
Other Descriptors
  • a small molecule(Cyc)
  • secondary alcohol(ChEBI)
Substituents
  • N/A
Direct Parent Secondary Alcohols
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility 1000.0 mg/mL Not Available
LogP 0.05 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 378 g/L ALOGPS
LogP 0.04 ALOGPS
LogP 0.25 ChemAxon
LogS 0.80 ALOGPS
pKa (strongest acidic) 17.26 ChemAxon
pKa (strongest basic) -1.8 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 17.43 ChemAxon
Polarizability 7.14 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-6M)
MS/MS Spectrum EI-B (JEOL JMS-D-3000)
MS/MS Spectrum EI-B (HITACHI M-80B)
MS/MS Spectrum EI-B (HITACHI RMU-7M)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Pancreas
  • Skin
  • Platelet
  • Stratum Corneum
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
83.3 +/- 132.8 uM Adult (>18 years old) Not Specified Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
Article_icon
22 +/- 56 uM Not Specified Both Normal Not Available
Urine Detected and not Quantified
Article_icon
Not Applicable Adult (>18 years old) Male Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
16.5 +/- 22.5 uM Adult (>18 years old) Not Specified Heart Transplant Not Available
Blood Detected and Quantified
Article_icon
8000.0 (7000.0-18000.0) uM Infant (0-1 year old) Both Isopropyl alcohol poisoning Fatal level
Blood Detected and Quantified
Article_icon
536.0 (66.0-1648.0) uM Adult (>18 years old) Both Alcohol intoxication Not Available
Associated Disorders and Diseases
Disease References
Isopropyl alcohol poisoning
  • Vicas IM, Beck R: Fatal inhalational isopropyl alcohol poisoning in a neonate. J Toxicol Clin Toxicol. 1993;31(3):473-81. Pubmed: 8355323 Link_out
    Alcoholism
    • Jones AW, Lund M, Andersson E: Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study. J Anal Toxicol. 1989 Jul-Aug;13(4):199-203. Pubmed: 2779169 Link_out
      Associated OMIM IDs None
      DrugBank ID DB02325 Link_out
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB008282
      KNApSAcK ID Not Available
      Chemspider ID 3644 Link_out
      KEGG Compound ID C01845 Link_out
      BioCyc ID Not Available
      BiGG ID Not Available
      Wikipedia Link Isopropyl alcohol Link_out
      NuGOwiki Link HMDB00863 Link_out
      Metagene Link HMDB00863 Link_out
      METLIN ID 4192 Link_out
      PubChem Compound 3776 Link_out
      PDB ID IOH Link_out
      ChEBI ID 17824 Link_out
      References
      Synthesis Reference Gu, Xiaoyan; Wu, Xiaolan; Ma, Guangyu. Process for preparation of hyper pure isopropyl alcohol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 6 pp.
      Material Safety Data Sheet (MSDS) Download (PDF)
      General References
      1. Lindberg M, Farm G, Scheynius A: Differential effects of sodium lauryl sulphate and non-anoic acid on the expression of CD1a and ICAM-1 in human epidermis. Acta Derm Venereol. 1991;71(5):384-8. Pubmed: 1684465 Link_out
      2. Lee CK, Ho PL, Chan NK, Mak A, Hong J, Lin CK: Impact of donor arm skin disinfection on the bacterial contamination rate of platelet concentrates. Vox Sang. 2002 Oct;83(3):204-8. Pubmed: 12366760 Link_out
      3. Specht C, Stoye I, Muller-Goymann CC: Comparative investigations to evaluate the use of organotypic cultures of transformed and native dermal and epidermal cells for permeation studies. Eur J Pharm Biopharm. 1998 Nov;46(3):273-8. Pubmed: 9885298 Link_out
      4. Zesch A, Schaefer H: [On interactions of drugs on and in the skin/comparative studies on the mutual influences of ethyleneglycol-monosalicylate and benzylnicotinate (author's transl)] Derm Beruf Umwelt. 1981;29(6):161-7. Pubmed: 7338200 Link_out
      5. NTP Toxicology and Carcinogenesis Studies of 1-Chloro-2-propanol (Technical Grade) (CAS NO. 127-00-4) in F344/N Rats and B6C3F1 Mice (Drinking Water Studies. Natl Toxicol Program Tech Rep Ser. 1998 Sep;477:1-264. Pubmed: 12571686 Link_out
      6. Liu P, Bergstrom TK: Quantitative evaluation of aqueous isopropyl alcohol enhancement on skin flux of terbutaline (sulfate). 2. Permeability contributions of equilibrated drug species across human skin in vitro. J Pharm Sci. 1996 Mar;85(3):320-5. Pubmed: 8699337 Link_out
      7. Froman RD, Owen SV, Murphy C: Isopropyl pad use in neonatal intensive care units. J Perinatol. 1998 May-Jun;18(3):216-20. Pubmed: 9659653 Link_out
      8. Bailey DG, Wilson TW, Johnson GE: A gas chromatographic method for measuring 6-mercaptopurine in serum. J Chromatogr. 1975 Sep 3;111(2):305-11. Pubmed: 1159009 Link_out
      9. Abdashirova NF: [Peculiarities of alternations in free radical oxidation in blood of humans contacting ozone at work] Aviakosm Ekolog Med. 1999;33(1):38-41. Pubmed: 10330571 Link_out
      10. Wittmann S, Gilg T, Dietz HG, Grantzow R, Peschel O, von Meyer L: [Isopropanol and acetone level in serum after preoperative surface disinfection with antiseptics containing isopropanol] Blutalkohol. 1992 Sep;29(5):326-35. Pubmed: 1389018 Link_out
      11. Anderson LM, Koseniauskas R, Burak ES, Moskal TJ, Gombar CT, Phillips JM, Sansone EB, Keimig S, Magee PN, Rice JM, et al.: Reduced blood clearance and increased urinary excretion of N-nitrosodimethylamine in patas monkeys exposed to ethanol or isopropyl alcohol. Cancer Res. 1992 Mar 15;52(6):1463-8. Pubmed: 1540953 Link_out
      12. Jones AE, Summers RL: Detection of isopropyl alcohol in a patient with diabetic ketoacidosis. J Emerg Med. 2000 Aug;19(2):165-8. Pubmed: 10903466 Link_out
      Enzymes
      Name: Phospholipase A2, membrane associated
      Reactions:
      • phosphatidylcholine + H2O = 1-acylglycerophosphocholine + a carboxylate [RN:R01313]
      Gene Name: PLA2G2A
      Uniprot ID: P14555 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      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: Peroxiredoxin-6
      Reactions:
      • 2 R'-SH + ROOH = R'-S-S-R' + H2O + ROH [RN:R07180]
      Gene Name: PRDX6
      Uniprot ID: P30041 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: L-xylulose reductase
      Reactions:
      • xylitol + NADP+ = L-xylulose + NADPH + H+ [RN:R01904]
      Gene Name: DCXR
      Uniprot ID: Q7Z4W1 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: Ribonuclease pancreatic
      Reactions:
      • Endonucleolytic cleavage to nucleoside 3'-phosphates and 3'-phosphooligonucleotides ending in Cp or Up with 2',3'-cyclic phosphate intermediates REFERENCE 1 AUTHORS Anfinsen, C.B. and White, F.H., Jr. TITLE The ribonucleases: occurrence, structure, and properties. JOURNAL In: Boyer, P.D., Lardy, H. and Myrback, K. (Eds.), The Enzymes, 2nd ed., vol. 5, Academic Press, New York, 1961, p. 95-122. REFERENCE 2 [PMID:14247667] AUTHORS BEARD JR, RAZZELL WE. TITLE PURIFICATION OF ALKALINE RIBONUCLEASE II FROM MITOCHONDRIAL AND SOLUBLE FRACTIONS OF LIVER. JOURNAL J. Biol. Chem. 239 (1964) 4186-93.
      Gene Name: RNASE1
      Uniprot ID: P07998 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: Adenosylhomocysteinase
      Reactions:
      • S-adenosyl-L-homocysteine + H2O = L-homocysteine + adenosine [RN:R00192]
      Gene Name: AHCY
      Uniprot ID: P23526 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: GTP cyclohydrolase 1
      Reactions:
      • GTP + H2O = formate + 7,8-dihydroneopterin 3'-triphosphate [RN:R00424]
      Gene Name: GCH1
      Uniprot ID: P30793 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: Chitotriosidase-1
      Reactions:
      • Random hydrolysis of N-acetyl-beta-D-glucosaminide (1->4)-beta-linkages in chitin and chitodextrins ALL_REAC (other) R01206 R02334 R06081(G) R06082(G) INHIBITOR Allosamidine [CPD:C05346]
      Gene Name: CHIT1
      Uniprot ID: Q13231 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: mRNA-capping enzyme
      Reactions:
      • a 5'-phosphopolynucleotide + H2O = a polynucleotide + phosphate [RN:R02249]
      Gene Name: RNGTT
      Uniprot ID: O60942 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Ganglioside GM2 activator
      Reactions:
        Gene Name: GM2A
        Uniprot ID: P17900 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: Tumor necrosis factor
        Reactions:
          Gene Name: TNF
          Uniprot ID: P01375 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: 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: Trypsin-2
                Reactions:
                • Preferential cleavage: Arg!, Lys! INHIBITOR Tos-Lys-CH2Cl [CPD:C00896]
                • Tos-Arg-CH2Cl [CPD:C02087]
                Gene Name: PRSS2
                Uniprot ID: P07478 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: Spliceosome RNA helicase BAT1
                Reactions:
                • ATP + H2O = ADP + phosphate
                Gene Name: BAT1
                Uniprot ID: Q13838 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: 1,2-dihydroxy-3-keto-5-methylthiopentene dioxygenase
                Reactions:
                  Gene Name: ADI1
                  Uniprot ID: Q9BV57 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