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Showing NP-Card for (S)-2-Methyl-1-butanol (NP0000979)

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Record Information
Version2.0
Created at2012-09-11 17:43:50 UTC
Updated at2022-01-05 19:13:31 UTC
NP-MRD IDNP0000979
Secondary Accession NumbersNone
Natural Product Identification
Common Name(S)-2-Methyl-1-butanol
Description(S)-2-Methyl-1-butanol, also known as sec-butylcarbinol or 2-methyl butanol-1, 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). (S)-2-Methyl-1-butanol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, (S)-2-methyl-1-butanol is considered to be a fatty alcohol lipid molecule. (S)-2-Methyl-1-butanol exists in all eukaryotes, ranging from yeast to humans. (S)-2-Methyl-1-butanol is a malt tasting compound. (S)-2-Methyl-1-butanol is found, on average, in the highest concentration within milk (cow) and it has also been detected, but not quantified, in several different foods, such as red raspberries, nectarines, carobs, wild leeks, and black-eyed pea. This could make (S)-2-methyl-1-butanol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0000979 ((S)-2-Methyl-1-butanol)


  Mrv1652305261923502D          

  6  5  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
    0.8250   -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
    0.8250    0.0000    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
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
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3D MOL for NP0000979 ((S)-2-Methyl-1-butanol)

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3D SDF for NP0000979 ((S)-2-Methyl-1-butanol)

  Mrv1652305261923502D          

  6  5  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
    0.8250   -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
    0.8250    0.0000    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
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000979

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3

> <INCHI_KEY>
QPRQEDXDYOZYLA-UHFFFAOYSA-N

> <FORMULA>
C5H12O

> <MOLECULAR_WEIGHT>
88.1482

> <EXACT_MASS>
88.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
10.992265927493843

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylbutan-1-ol

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
1.1702947723333335

> <ALOGPS_LOGS>
-0.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.501123795275216

> <JCHEM_PKA_STRONGEST_BASIC>
-1.7048084519466205

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
26.606499999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.20e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-1-butanol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0000979 ((S)-2-Methyl-1-butanol)
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PDB for NP0000979 ((S)-2-Methyl-1-butanol)
HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.850  -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  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    5                                                            
CONECT    3    1    5                                                       
CONECT    4    5    6                                                       
CONECT    5    2    3    4                                                  
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0000979 ((S)-2-Methyl-1-butanol)
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SMILES for NP0000979 ((S)-2-Methyl-1-butanol)
CCC(C)CO
Download
INCHI for NP0000979 ((S)-2-Methyl-1-butanol)
InChI=1S/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3
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Synonyms
ValueSource
2-Methyl butanol-1ChEBI
2-Methyl-1-butanolChEBI
2-Methyl-N-butanolChEBI
2-MethylbutanolChEBI
2-Methylbutyl alcoholChEBI
Active amyl alcoholChEBI
Active primary amyl alcoholChEBI
CH3CH2CH(CH3)CH2OHChEBI
Methyl-2-butan-1-olChEBI
Primary active amyl alcoholChEBI
Sec-butylcarbinolChEBI
(+/-)-2-methyl-1-butanolHMDB
(1)-2-Methylbutan-1-olHMDB
(S)-(-)-2-Methyl-1-butanolHMDB
(S)-2-Methylbutan-1-olHMDB
2-Methyl-(.+/-.)-1-butanolHMDB
2-Methyl-(2S)-1-butanolHMDB
2-Methyl-(S)-1-butanolHMDB
2-Methylbutan-1-olHMDB
D-2-METHYL-1-butanolHMDB
DL-2-Methyl-1-butanolHMDB
DL-2-METHYL-1-butanol, practHMDB
DL-Sec-butyl carbinolHMDB
L-2-Methyl-1-butanolHMDB
Sec-butyl carbinolHMDB
Chemical FormulaC5H12O
Average Mass88.1482 Da
Monoisotopic Mass88.08882 Da
IUPAC Name2-methylbutan-1-ol
Traditional Name2-methyl-1-butanol
CAS Registry Number1565-80-6
SMILES
CCC(C)CO
InChI Identifier
InChI=1S/C5H12O/c1-3-5(2)4-6/h5-6H,3-4H2,1-2H3
InChI KeyQPRQEDXDYOZYLA-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-10-13View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-06-09View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-01-05View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
Aloe arborescensLOTUS Database
Ananas comosusLOTUS Database
Brassica oleracea var. gongylodesFooDB
Bystropogon plumosusLOTUS Database
Camellia sinensisLOTUS Database
Capsicum annuumFooDB
Foeniculum vulgareLOTUS Database
Glycine maxFooDB
Gossypium hirsutumLOTUS Database
Juglans nigraLOTUS Database
Malus pumilaFooDB
Mangifera indicaLOTUS Database
Mentha spicataFooDB
Myrtus communisLOTUS Database
Paeonia lactifloraLOTUS Database
Phaseolus vulgarisFooDB
Plectranthus glabratusLOTUS Database
Plumeria rubraLOTUS Database
Prunus aviumFooDB
    • Bernalte, M. J., Hernandez, M. T., Vidal-Aragon, M. C. & Sabio, E. (1999) Physical, chemical, fla...
Solanum lycopersicumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Spondias mombinLOTUS Database
Trifolium pratenseLOTUS Database
Tuber melanosporumLOTUS Database
Vaccinium myrtillusFooDB
Vaccinium vitis-idaeaLOTUS Database
Vigna radiataFooDB
Zea maysLOTUS Database
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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility42 g/LALOGPS
logP1.24ALOGPS
logP1.17ChemAxon
logS-0.32ALOGPS
pKa (Strongest Acidic)17.5ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.61 m³·mol⁻¹ChemAxon
Polarizability10.99 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031527  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008130  
KNApSAcK IDNot Available
Chemspider ID8398  
KEGG Compound IDNot Available
BioCyc IDCPD-7033  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8723  
PDB IDNot Available
ChEBI ID48945  
Good Scents IDNot Available
References
General References
  1. Amaro AL, Fundo JF, Oliveira A, Beaulieu JC, Fernandez-Trujillo JP, Almeida DP: 1-methylcyclopropene effects on temporal changes of aroma volatiles and phytochemicals of fresh-cut cantaloupe. J Sci Food Agric. 2013 Mar 15;93(4):828-37. doi: 10.1002/jsfa.5804. Epub 2012 Jul 20. [PubMed:22821412  ] 
  2. Baena-Ruano S, Santos-Duenas IM, Mauricio JC, Garcia-Garcia I: Relationship between changes in the total concentration of acetic acid bacteria and major volatile compounds during the acetic acid fermentation of white wine. J Sci Food Agric. 2010 Dec;90(15):2675-81. doi: 10.1002/jsfa.4139. [PubMed:20812374  ] 
  3. Cann AF, Liao JC: Production of 2-methyl-1-butanol in engineered Escherichia coli. Appl Microbiol Biotechnol. 2008 Nov;81(1):89-98. doi: 10.1007/s00253-008-1631-y.  Epub 2008 Aug 29. [PubMed:18758769  ] 
  4. Silva WD, Millar JG, Hanks LM, Costa CM, Leite MOG, Tonelli M, Bento JMS: Interspecific Cross-Attraction between the South American Cerambycid Beetles Cotyclytus curvatus and Megacyllene acuta is Averted by Minor Pheromone Components. J Chem Ecol. 2018 Mar;44(3):268-275. doi: 10.1007/s10886-018-0933-5. Epub 2018 Feb 12. [PubMed:29430578  ] 
  5.  (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .