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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
Thumb
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
Download

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
Download

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

$$$$
Download

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
Download

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
Download

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
ValueSource
1-Butyl alcoholChEBI
1-HydroxybutaneChEBI
BuOHChEBI
N-Butan-1-olChEBI
N-ButanolChEBI
N-Butyl alcoholChEBI
N-ButylalkoholChEBI
Propyl carbinolChEBI
Butan-1-olKegg
ButanolHMDB
Butyl alcoholHMDB
Butyl hydroxideHMDB
HemostypHMDB
MethylolpropaneHMDB
PropylcarbinolHMDB
Alcohol, N-butylHMDB
N Butyl alcoholHMDB
Alcohol, butylHMDB
1 ButanolHMDB
N ButanolHMDB
1-ButanolChEBI
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
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Camellia sinensisPlant
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
Carica papaya L.FooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
Citrullus lanatusFooDB
Coffea arabica L.Plant
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Glycine maxFooDB
Lagopus mutaFooDB
Laurus nobilis L.FooDB
LeporidaeFooDB
Lepus timidusFooDB
Malus pumilaFooDB
Medicago sativaPlant
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Prunus aviumFooDB
    • J. P. Mattheis, D. A. Buchanan, and J. K. Fellman Volatile Constituents of Bing Sweet Cherry Frui...
Pyrus communisFooDB
    • D. E. Heinz and W. C. Jennings. Volatile components of Bartlett Pear. V. Journal of Food Sci., 19...
Ribes nigrumFooDB
Sida galheirensisPlant
Solanum lycopersicum Mill.Plant
Solanum lycopersicum var. lycopersicumFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Vaccinium corymbosumFooDB
Vaccinium myrtillusFooDB
Vigna radiataFooDB
Zea mays L.FooDB
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
  1. 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 Emphasis Tumor Immunol. 1993 May 4;13(4):232-42. [PubMed:8334107 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  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 ]
  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 ]
  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 ]
  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 ]
  12. Wulkan RW, Huijskes-Heins MI, Leijnse B: Hydrophobic properties of alkaline phosphatases. Int J Biochem. 1986;18(11):1045-51. [PubMed:3803695 ]
  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 ]
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