Showing NP-Card for 1-Butanol (NP0000127)

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Record Information
Version2.0
Created at2006-08-13 16:50:24 UTC
Updated at2022-01-12 18:59:14 UTC
NP-MRD IDNP0000127
Secondary Accession Numbers
  • NP0055076
Natural Product Identification
Common Name1-Butanol
Description1-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. It has been found in Bacillus, Clostridium, Escherichia, Lactobacillus, Pseudomonas, Saccharomyces, Synechococcus and Thermoanaerobacterium.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000127 (1-Butanol)

  Mrv1652303202019002D          

  5  4  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
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3D MOL for NP0000127 (1-Butanol)

HMDB0004327
     RDKit          3D
1-Butanol
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.5192   -0.3178    0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9588   -0.1222   -0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4660   -0.4929   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344    0.2620    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4162    1.6179   -0.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6395   -0.3839    0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -1.2713    1.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3705    0.5433    1.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5632   -0.7271   -1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1232    0.9361   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6415   -1.5787   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7324   -0.2721   -1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.0802    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4635   -0.1405    0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    1.8670   -0.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
M  END
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3D SDF for NP0000127 (1-Butanol)

  Mrv1652303202019002D          

  5  4  0  0  0  0            999 V2000
    2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000127

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCO

> <INCHI_IDENTIFIER>
InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3

> <INCHI_KEY>
LRHPLDYGYMQRHN-UHFFFAOYSA-N

> <FORMULA>
C4H10O

> <MOLECULAR_WEIGHT>
74.1216

> <EXACT_MASS>
74.073164942

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
9.214856371458051

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
butan-1-ol

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
0.805321946

> <ALOGPS_LOGS>
0.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.954258074443697

> <JCHEM_PKA_STRONGEST_BASIC>
-1.944007518238327

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
22.1349

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butanol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0000127 (1-Butanol)

HMDB0004327
     RDKit          3D
1-Butanol
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.5192   -0.3178    0.8754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9588   -0.1222   -0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4660   -0.4929   -0.6766 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4344    0.2620    0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4162    1.6179   -0.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6395   -0.3839    0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2262   -1.2713    1.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3705    0.5433    1.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5632   -0.7271   -1.1970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1232    0.9361   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6415   -1.5787   -0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7324   -0.2721   -1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1450    0.0802    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4635   -0.1405    0.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    1.8670   -0.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
M  END
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PDB for NP0000127 (1-Butanol)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for NP0000127 (1-Butanol)

COMPND    HMDB0004327
HETATM    1  C1  UNL     1      -1.519  -0.318   0.875  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.959  -0.122  -0.488  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.466  -0.493  -0.677  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.434   0.262   0.189  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.416   1.618  -0.003  1.00  0.00           O  
HETATM    6  H1  UNL     1      -2.639  -0.384   0.757  1.00  0.00           H  
HETATM    7  H2  UNL     1      -1.226  -1.271   1.353  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.370   0.543   1.558  1.00  0.00           H  
HETATM    9  H4  UNL     1      -1.563  -0.727  -1.197  1.00  0.00           H  
HETATM   10  H5  UNL     1      -1.123   0.936  -0.779  1.00  0.00           H  
HETATM   11  H6  UNL     1       0.642  -1.579  -0.536  1.00  0.00           H  
HETATM   12  H7  UNL     1       0.732  -0.272  -1.733  1.00  0.00           H  
HETATM   13  H8  UNL     1       1.145   0.080   1.266  1.00  0.00           H  
HETATM   14  H9  UNL     1       2.463  -0.140   0.100  1.00  0.00           H  
HETATM   15  H10 UNL     1       2.101   1.867  -0.686  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    9   10
CONECT    3    4   11   12
CONECT    4    5   13   14
CONECT    5   15
END
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SMILES for NP0000127 (1-Butanol)

CCCCO
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INCHI for NP0000127 (1-Butanol)

InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3
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View in JSmol
Synonyms
Chemical FormulaC4H10O
Average Mass74.1216 Da
Monoisotopic Mass74.07316 Da
IUPAC Namebutan-1-ol
Traditional Namebutanol
CAS Registry Number71-36-3
SMILES
CCCCO
InChI Identifier
InChI=1S/C4H10O/c1-2-3-4-5/h5H,2-4H2,1H3
InChI KeyLRHPLDYGYMQRHN-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-12View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
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-89.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility63.2 mg/mL at 25 °CNot Available
LogP0.88Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility158 g/LALOGPS
logP0.84ALOGPS
logP0.81ChemAxon
logS0.33ALOGPS
pKa (Strongest Acidic)16.95ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity22.13 m³·mol⁻¹ChemAxon
Polarizability9.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004327
DrugBank IDDB02145
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031032
KNApSAcK IDC00035814
Chemspider ID258
KEGG Compound IDC06142
BioCyc IDBUTANOL
BiGG IDNot Available
Wikipedia LinkN-Butanol
METLIN ID7052
PubChem Compound263
PDB ID1BO
ChEBI ID28885
Good Scents IDrw1029131
References
General References