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Record Information
Version3.6
Creation Date2007-04-12 20:13:40 UTC
Update Date2014-12-01 23:15:34 UTC
HMDB IDHMDB06006
Secondary Accession NumbersNone
Metabolite Identification
Common NameIsobutanol
DescriptionIsobutanol is an aliphatic alcohol. Isobutanol is a colorless, flammable, organic compound with a characteristic smell. Isobutanol is widely used in industry, as a solvent in chemical reactions, as well as being a useful starting material for organic synthesis. Isobutanol is a flammable liquid that should be stored and used in well-ventilated areas. It is moderately irritating to the skin and greatly irritating to the eyes, mucous membranes and respiratory tract. Exposure to high concentrations of its vapour can cause temporary narcosis. Isobutanol is occasionally found as a volatile component of urine and arises from gut microbial metabolism. Isobutanol is used as one of the markers to measure occupational exposure to a mixture of solvents. Aliphatic alcohols levels increase in both diabetes mellitus and insulin-dependent diabetes patients. (PMID: 5556886 , 2477620 , 9143482 , 7627316 , 2288731 ).
Structure
Thumb
Synonyms
  1. 1-Hydroxymethylpropane
  2. 1-Propanol, 2-methyl-
  3. 2-Methyl propanol
  4. 2-Methyl-1-propanol
  5. 2-Methyl-1-propanyl alcohol
  6. 2-Methylpropan-1-ol
  7. 2-MethylpropanoI
  8. 2-Methylpropanol
  9. 2-Methylpropanol-1
  10. 2-Methylpropyl alcohol
  11. Alcool isobutylique
  12. I-Butanol
  13. I-Butyl alcohol
  14. IBA
  15. Iso-butyl alcohol
  16. Isobutanol
  17. Isobutyl alcohol
  18. Isopropyl carbitol
  19. Isopropylcarbinol
  20. Methyl-2 propanol-1
Chemical FormulaC4H10O
Average Molecular Weight74.1216
Monoisotopic Molecular Weight74.073164942
IUPAC Name2-methylpropan-1-ol
Traditional Nameisobutanol
CAS Registry Number78-83-1
SMILES
CC(C)CO
InChI Identifier
InChI=1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3
InChI KeyZXEKIIBDNHEJCQ-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlcohols and Polyols
Sub ClassPrimary Alcohols
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Fatty alcohols(Lipidmaps)
  • a small molecule(Cyc)
  • alkyl alcohol(ChEBI)
  • primary alcohol(ChEBI)
Substituents
  • N/A
Direct ParentPrimary Alcohols
Ontology
StatusDetected and Not Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-108 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility85 mg/mL at 25 °CNot Available
LogP0.76HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility140.0ALOGPS
logP0.6ALOGPS
logP0.73ChemAxon
logS0.28ALOGPS
pKa (Strongest Acidic)17.33ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.01 m3·mol-1ChemAxon
Polarizability9.07 Å3ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative Colitis
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative colitis 
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003274
KNApSAcK IDNot Available
Chemspider ID6312
KEGG Compound IDC14710
BioCyc IDISOBUTANOL
BiGG IDNot Available
Wikipedia Linkhttp://en.wikipedia.org/wiki/Isobutanol
NuGOwiki LinkHMDB06006
Metagene LinkHMDB06006
METLIN IDNot Available
PubChem Compound6560
PDB IDNot Available
ChEBI ID46645
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. Pubmed: 5556886
  2. Bilzer N, Schmutte P, Jehs M, Penners BM: [Kinetics of aliphatic alcohols (methanol, propanol-1 and isobutanol) in the presence of alcohol in the human body]. Blutalkohol. 1990 Nov;27(6):385-409. Pubmed: 2288731
  3. Inglik N, Rudenko BA, Kakhnovskii IM, Koroleva TV: [Gas chromatographic study of the composition of the volatile components of the urine in normal subjects and patients with diabetes mellitus]. Lab Delo. 1989;(8):24-7. Pubmed: 2477620
  4. Norback D, Bjornsson E, Janson C, Widstrom J, Boman G: Asthmatic symptoms and volatile organic compounds, formaldehyde, and carbon dioxide in dwellings. Occup Environ Med. 1995 Jun;52(6):388-95. Pubmed: 7627316
  5. Kruszewski FH, Walker TL, DiPasquale LC: Evaluation of a human corneal epithelial cell line as an in vitro model for assessing ocular irritation. Fundam Appl Toxicol. 1997 Apr;36(2):130-40. Pubmed: 9143482

Enzymes

General function:
Involved in arylesterase activity
Specific function:
Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:
PON3
Uniprot ID:
Q15166
Molecular weight:
39607.185
General function:
Involved in arylesterase activity
Specific function:
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:
PON1
Uniprot ID:
P27169
Molecular weight:
39730.99
General function:
Involved in arylesterase activity
Specific function:
Capable of hydrolyzing lactones and a number of aromatic carboxylic acid esters. Has antioxidant activity. Is not associated with high density lipoprotein. Prevents LDL lipid peroxidation, reverses the oxidation of mildly oxidized LDL, and inhibits the ability of MM-LDL to induce monocyte chemotaxis.
Gene Name:
PON2
Uniprot ID:
Q15165
Molecular weight:
39380.535
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPI
Uniprot ID:
P09923
Molecular weight:
56811.695
General function:
Involved in acid phosphatase activity
Specific function:
Not Available
Gene Name:
ACP2
Uniprot ID:
P11117
Molecular weight:
48343.92
General function:
Involved in catalytic activity
Specific function:
This isozyme may play a role in skeletal mineralization.
Gene Name:
ALPL
Uniprot ID:
P05186
Molecular weight:
57304.435
General function:
Involved in hydrolase activity
Specific function:
Involved in osteopontin/bone sialoprotein dephosphorylation. Its expression seems to increase in certain pathological states such as Gaucher and Hodgkin diseases, the hairy cell, the B-cell, and the T-cell leukemias.
Gene Name:
ACP5
Uniprot ID:
P13686
Molecular weight:
36598.47
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPPL2
Uniprot ID:
P10696
Molecular weight:
57376.515
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
General function:
Involved in zinc ion binding
Specific function:
Converts sorbitol to fructose. Part of the polyol pathway that plays an important role in sperm physiology. May play a role in the sperm motility by providing an energetic source for sperm (By similarity).
Gene Name:
SORD
Uniprot ID:
Q00796
Molecular weight:
38324.25
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a variety of aromatic and aliphatic aldehydes to their corresponding alcohols. Catalyzes the reduction of mevaldate to mevalonic acid and of glyceraldehyde to glycerol. Has broad substrate specificity. In vitro substrates include succinic semialdehyde, 4-nitrobenzaldehyde, 1,2-naphthoquinone, methylglyoxal, and D-glucuronic acid. Plays a role in the activation of procarcinogens, such as polycyclic aromatic hydrocarbon trans-dihydrodiols, and in the metabolism of various xenobiotics and drugs, including the anthracyclines doxorubicin (DOX) and daunorubicin (DAUN).
Gene Name:
AKR1A1
Uniprot ID:
P14550
Molecular weight:
36572.71
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH4
Uniprot ID:
P08319
Molecular weight:
40221.335
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1B
Uniprot ID:
P00325
Molecular weight:
39835.17
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH1A
Uniprot ID:
P07327
Molecular weight:
39858.37
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ADH6
Uniprot ID:
P28332
Molecular weight:
39072.275
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Plays an important role in the degradation of dermatan and keratan sulfates.
Gene Name:
GUSB
Uniprot ID:
P08236
Molecular weight:
74731.46
General function:
Involved in alpha-L-fucosidase activity
Specific function:
Alpha-L-fucosidase is responsible for hydrolyzing the alpha-1,6-linked fucose joined to the reducing-end N-acetylglucosamine of the carbohydrate moieties of glycoproteins.
Gene Name:
FUCA2
Uniprot ID:
Q9BTY2
Molecular weight:
54066.31
General function:
Involved in zinc ion binding
Specific function:
Catalyzes the reduction of trans-2-enoyl-CoA to acyl-CoA with chain length from C6 to C16 in an NADPH-dependent manner with preference to medium chain length substrate. May have a role in the mitochondrial synthesis of fatty acids.
Gene Name:
MECR
Uniprot ID:
Q9BV79
Molecular weight:
32228.0
General function:
Involved in phosphatidylcholine-retinol O-acyltransfera
Specific function:
Transfers the acyl group from the sn-1 position of phosphatidylcholine to all-trans retinol, producing all-trans retinyl esters. Retinyl esters are storage forms of vitamin A. LRAT plays a critical role in vision. It provides the all-trans retinyl ester substrates for the isomerohydrolase which processes the esters into 11-cis-retinol in the retinal pigment epithelium; due to a membrane-associated alcohol dehydrogenase, 11 cis-retinol is oxidized and converted into 11-cis-retinaldehyde which is the chromophore for rhodopsin and the cone photopigments.
Gene Name:
LRAT
Uniprot ID:
O95237
Molecular weight:
25702.635
General function:
Involved in sequence-specific DNA binding transcription factor activity
Specific function:
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital responsive element module of the human CYP2B6 gene and the CYP3A4 xenobiotic response element
Gene Name:
NR1I3
Uniprot ID:
Q14994
Molecular weight:
39942.1
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
ZADH2
Uniprot ID:
Q8N4Q0
Molecular weight:
40140.1
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the cofactor-independent reversible oxidation of gamma-hydroxybutyrate (GHB) to succinic semialdehyde (SSA) coupled to reduction of 2-ketoglutarate (2-KG) to D-2-hydroxyglutarate (D-2-HG). D,L-3-hydroxyisobutyrate and L-3-hydroxybutyrate (L-3-OHB) are also substrates for HOT with 10-fold lower activities.
Gene Name:
ADHFE1
Uniprot ID:
Q8IWW8
Molecular weight:
50307.42
General function:
Involved in catalytic activity
Specific function:
Catalyzes the reduction of fatty acyl-CoA to fatty alcohols. The preferred substrates are C16, C18, C18:1 and C18:2 but low activity can be observed with C10-C14 substrates.
Gene Name:
FAR2
Uniprot ID:
Q96K12
Molecular weight:
59437.92
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Acyltransferase that predominantly esterify long chain (wax) alcohols with acyl-CoA-derived fatty acids to produce wax esters. Wax esters are enriched in sebum, suggesting that it plays a central role in lipid metabolism in skin. Has no activity using decyl alcohol and significantly prefers the C16 and C18 alcohols. May also have 2-acylglycerol O-acyltransferase (MGAT) and acyl-CoA:retinol acyltransferase (ARAT) activities, to catalyze the synthesis of diacylglycerols and retinyl esters; however this activity is unclear in vivo.
Gene Name:
AWAT2
Uniprot ID:
Q6E213
Molecular weight:
38093.25
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
May have weak glycosidase activity towards glucuronylated steroids. However, it lacks essential active site Glu residues at positions 239 and 872, suggesting it may be inactive as a glycosidase in vivo. May be involved in the regulation of calcium and phosphorus homeostasis by inhibiting the synthesis of active vitamin D (By similarity). Essential factor for the specific interaction between FGF23 and FGFR1 (By similarity). The Klotho peptide generated by cleavage of the membrane-bound isoform may be an anti-aging circulating hormone which would extend life span by inhibiting insulin/IGF1 signaling (By similarity).
Gene Name:
KL
Uniprot ID:
Q9UEF7
Molecular weight:
116179.815
General function:
Involved in acid phosphatase activity
Specific function:
Dephosphorylates receptor tyrosine-protein kinase erbB-4 and inhibits the ligand-induced proteolytic cleavage.
Gene Name:
ACPT
Uniprot ID:
Q9BZG2
Molecular weight:
46089.015
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs (By similarity).
Gene Name:
CES5A
Uniprot ID:
Q6NT32
Molecular weight:
63925.82
General function:
Involved in acid phosphatase activity
Specific function:
Not Available
Gene Name:
ACPL2
Uniprot ID:
Q8TE99
Molecular weight:
55239.395
General function:
Involved in zinc ion binding
Specific function:
Not Available
Gene Name:
VAT1L
Uniprot ID:
Q9HCJ6
Molecular weight:
45899.2
General function:
Involved in zinc ion binding
Specific function:
May be involved in the generation of reactive oxygen species (ROS). Has low NADPH-dependent naphtoquinone reductase activity, with a preference for 1,2-naphtoquinone over 1,4- naphtoquinone. Has low NADPH-dependent diamine reductase activity (in vitro)
Gene Name:
TP53I3
Uniprot ID:
Q53FA7
Molecular weight:
35535.9
General function:
Involved in zinc ion binding
Specific function:
Possesses ATPase activity. Plays a part in calcium-regulated keratinocyte activation in epidermal repair mechanisms. Has no effect on cell proliferation
Gene Name:
VAT1
Uniprot ID:
Q99536
Molecular weight:
41920.0
General function:
Involved in zinc ion binding
Specific function:
Appears to be a potent inhibitor of regeneration following spinal cord injury
Gene Name:
RTN4IP1
Uniprot ID:
Q8WWV3
Molecular weight:
43589.4