Showing NP-Card for Isobutanol (NP0000131)

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Record Information
Version2.0
Created at2007-04-12 20:13:40 UTC
Updated at2022-04-04 18:44:35 UTC
NP-MRD IDNP0000131
Secondary Accession NumbersNone
Natural Product 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 ). Isobutanol is a microbial metabolite found in Clostridium, Cupriavidus, Escherichia, Geobacillus, Saccharomyces and Synechococcus (PMID:19946322 ).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0000131 (Isobutanol)

  Mrv1652305271900172D          

  5  4  0  0  0  0            999 V2000
   18.6164   -3.7814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1875   -3.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9020   -3.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4730   -3.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1875   -4.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
M  END
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3D MOL for NP0000131 (Isobutanol)

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3D SDF for NP0000131 (Isobutanol)
  Mrv1652305271900172D          

  5  4  0  0  0  0            999 V2000
   18.6164   -3.7814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1875   -3.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9020   -3.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4730   -3.3689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1875   -4.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000131

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3

> <INCHI_KEY>
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N

> <FORMULA>
C4H10O

> <MOLECULAR_WEIGHT>
74.1216

> <EXACT_MASS>
74.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
9.065725629445156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylpropan-1-ol

> <ALOGPS_LOGP>
0.60

> <JCHEM_LOGP>
0.7257261073333335

> <ALOGPS_LOGS>
0.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.32703147494006

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7809564328612169

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
22.005499999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isobutanol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0000131 (Isobutanol)
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PDB for NP0000131 (Isobutanol)
HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      34.751  -7.059   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      32.083  -7.059   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      33.417  -6.289   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.750  -6.289   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      32.083  -8.599   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2    3    4    5                                                  
CONECT    3    1    2                                                       
CONECT    4    2                                                            
CONECT    5    2                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END

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3D PDB for NP0000131 (Isobutanol)
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SMILES for NP0000131 (Isobutanol)
CC(C)CO
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INCHI for NP0000131 (Isobutanol)
InChI=1S/C4H10O/c1-4(2)3-5/h4-5H,3H2,1-2H3
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Synonyms
Chemical FormulaC4H10O
Average Mass74.1216 Da
Monoisotopic Mass74.07316 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-04-04View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as primary alcohols. Primary alcohols are compounds comprising the primary alcohol functional group, with the general structure RCOH (R=alkyl, aryl).
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct ParentPrimary alcohols  
Alternative Parents
Substituents
  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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 CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility140 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity22.01 m³·mol⁻¹ChemAxon
Polarizability9.07 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006006  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003274  
KNApSAcK IDNot Available
Chemspider ID6312  
KEGG Compound IDC14710  
BioCyc IDISOBUTANOL  
BiGG IDNot Available
Wikipedia LinkIsobutanol  
METLIN IDNot Available
PubChem Compound6560  
PDB IDNot Available
ChEBI ID46645  
Good Scents IDNot Available
References
General References
  1. 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  ] 
  2. Gu P, Liu L, Ma Q, Dong Z, Wang Q, Xu J, Huang Z, Li Q: Metabolic engineering of Escherichia coli for the production of isobutanol: a review. World J Microbiol Biotechnol. 2021 Sep 6;37(10):168. doi: 10.1007/s11274-021-03140-0. [PubMed:34487256  ]