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Showing NP-Card for 2-Heptanone (NP0000731)

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Record Information
Version2.0
Created at2006-08-13 02:57:08 UTC
Updated at2021-10-07 20:41:04 UTC
NP-MRD IDNP0000731
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Heptanone
Description2-Heptanone, also known as butylacetone or heptan-2-one, belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 2-heptanone is considered to be an oxygenated hydrocarbon lipid molecule. 2-Heptanone is a ketone with the molecular formula C7H14O. 2-Heptanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 2-Heptanone exists in all living species, ranging from bacteria to humans. 2-Heptanone is a sweet, cinnamon, and coconut tasting compound. 2-Heptanone is found, on average, in the highest concentration within a few different foods, such as corns, cow milk, and peppermints. 2-Heptanone has also been detected, but not quantified in several different foods, such as tarragons, blackberries, tortilla chips, ceylon cinnamons, and evergreen blackberries. 2-Heptanone is one of the metabolites of n-heptane found in the urine of employees exposed to heptane in shoe and tire factories. 2-Heptanone, with regard to humans, has been found to be associated with several diseases such as ulcerative colitis, nonalcoholic fatty liver disease, crohn's disease, and hepatic encephalopathy; 2-heptanone has also been linked to the inborn metabolic disorder celiac disease. It is a colorless to white liquid with a banana-like, fruity odor.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000731 (2-Heptanone)


  Mrv1652303202018592D          

  8  7  0  0  0  0            999 V2000
   -0.5445   -0.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    0.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2477    0.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8824   -0.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9715   -0.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2201    0.9650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6095    0.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3092   -0.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
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3D MOL for NP0000731 (2-Heptanone)

HMDB0003671
     RDKit          3D
2-Heptanone
 22 21  0  0  0  0  0  0  0  0999 V2000
   -3.0037    0.5943   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5054   -0.4712    0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980   -0.9213    0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1045    0.2129    0.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2541   -0.3441    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3161    0.6958    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    0.2733   -0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917    1.8656    0.3623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5336    0.5870   -1.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9471    1.6206    0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0945    0.4341   -0.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6115   -0.1394    1.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1547   -1.3687    0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0957   -1.3612   -0.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8144   -1.6513    1.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515    0.6114    1.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476    0.9801   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864   -0.8245   -0.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5604   -1.1525    0.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    1.1268   -0.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1534   -0.2936    0.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -0.4743   -1.0705 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
  5  6  1  0
  6  7  1  0
  6  8  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
M  END
Download

3D SDF for NP0000731 (2-Heptanone)


  Mrv1652303202018592D          

  8  7  0  0  0  0            999 V2000
   -0.5445   -0.2930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827    0.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2477    0.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8824   -0.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9715   -0.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2201    0.9650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6095    0.0552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3092   -0.3826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000731

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3

> <INCHI_KEY>
CATSNJVOTSVZJV-UHFFFAOYSA-N

> <FORMULA>
C7H14O

> <MOLECULAR_WEIGHT>
114.1855

> <EXACT_MASS>
114.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.314468281537355

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
heptan-2-one

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
2.140521650333333

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.64344979346997

> <JCHEM_PKA_STRONGEST_BASIC>
-7.270866222403733

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
34.6247

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-heptanone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000731 (2-Heptanone)

HMDB0003671
     RDKit          3D
2-Heptanone
 22 21  0  0  0  0  0  0  0  0999 V2000
   -3.0037    0.5943   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5054   -0.4712    0.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980   -0.9213    0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1045    0.2129    0.3490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2541   -0.3441    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3161    0.6958    0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7069    0.2733   -0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917    1.8656    0.3623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5336    0.5870   -1.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9471    1.6206    0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0945    0.4341   -0.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6115   -0.1394    1.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1547   -1.3687    0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0957   -1.3612   -0.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8144   -1.6513    1.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0515    0.6114    1.3735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476    0.9801   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2864   -0.8245   -0.9907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5604   -1.1525    0.7299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3609    1.1268   -0.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1534   -0.2936    0.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6323   -0.4743   -1.0705 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
  5  6  1  0
  6  7  1  0
  6  8  2  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
M  END
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PDB for NP0000731 (2-Heptanone)

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      -1.016  -0.547   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.341   0.180   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.329   0.264   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.647  -0.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.680  -0.463   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.278   1.801   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.004   0.103   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.311  -0.714   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2    7                                                       
CONECT    5    3                                                            
CONECT    6    3                                                            
CONECT    7    4    8                                                       
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for NP0000731 (2-Heptanone)

COMPND    HMDB0003671
HETATM    1  C1  UNL     1      -3.004   0.594  -0.337  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.505  -0.471   0.582  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.098  -0.921   0.258  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.105   0.213   0.349  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.254  -0.344   0.009  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.316   0.696   0.069  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.707   0.273  -0.247  1.00  0.00           C  
HETATM    8  O1  UNL     1       2.092   1.866   0.362  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.534   0.587  -1.337  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.947   1.621   0.134  1.00  0.00           H  
HETATM   11  H3  UNL     1      -4.094   0.434  -0.511  1.00  0.00           H  
HETATM   12  H4  UNL     1      -2.611  -0.139   1.633  1.00  0.00           H  
HETATM   13  H5  UNL     1      -3.155  -1.369   0.466  1.00  0.00           H  
HETATM   14  H6  UNL     1      -1.096  -1.361  -0.742  1.00  0.00           H  
HETATM   15  H7  UNL     1      -0.814  -1.651   1.056  1.00  0.00           H  
HETATM   16  H8  UNL     1      -0.051   0.611   1.374  1.00  0.00           H  
HETATM   17  H9  UNL     1      -0.348   0.980  -0.391  1.00  0.00           H  
HETATM   18  H10 UNL     1       1.286  -0.824  -0.991  1.00  0.00           H  
HETATM   19  H11 UNL     1       1.560  -1.152   0.730  1.00  0.00           H  
HETATM   20  H12 UNL     1       4.361   1.127  -0.521  1.00  0.00           H  
HETATM   21  H13 UNL     1       4.153  -0.294   0.622  1.00  0.00           H  
HETATM   22  H14 UNL     1       3.632  -0.474  -1.070  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12   13
CONECT    3    4   14   15
CONECT    4    5   16   17
CONECT    5    6   18   19
CONECT    6    7    8    8
CONECT    7   20   21   22
END
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SMILES for NP0000731 (2-Heptanone)

CCCCCC(C)=O
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INCHI for NP0000731 (2-Heptanone)

InChI=1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3
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Synonyms
ValueSource
ButylacetoneChEBI
Methyl N-amyl ketoneChEBI
Methyl pentyl ketoneChEBI
N-Amyl methyl ketoneChEBI
N-Pentyl methyl ketoneChEBI
Heptan-2-oneKegg
1-MethylhexanalHMDB
2-OxoheptaneHMDB
Amyl methyl ketoneHMDB
Methyl amyl ketoneHMDB
Methyl N-pentyl ketoneHMDB
Pentyl methyl ketoneHMDB
Methyl-N-amyl ketoneHMDB
2-HeptanoneChEBI
Chemical FormulaC7H14O
Average Mass114.1855 Da
Monoisotopic Mass114.10447 Da
IUPAC Nameheptan-2-one
Traditional Name2-heptanone
CAS Registry Number110-43-0
SMILES
CCCCCC(C)=O
InChI Identifier
InChI=1S/C7H14O/c1-3-4-5-6-7(2)8/h3-6H2,1-2H3
InChI KeyCATSNJVOTSVZJV-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
Amorphophallus eichleriLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anethum foeniculumPlant
Anser anserFooDB
Apis melliferaLOTUS Database
Artemisia dracunculusFooDB
Arum maculatumKNApSAcK Database
Aspalathus linearisLOTUS Database
Averrhoa carambolaKNApSAcK Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
Capsicum annuum var. annuumFooDB
Carica papaya L.FooDB
Centipeda minimaLOTUS Database
CervidaeFooDB
Cervus canadensisFooDB
Cinnamomum verumFooDB
Citrullus lanatusFooDB
Coffea arabicaKNApSAcK Database
Coffea arabica L.Plant
ColumbaFooDB
ColumbidaeFooDB
Daucus carotaLOTUS Database
Dromaius novaehollandiaeFooDB
Elettaria cardamomumFooDB
Equus caballusFooDB
Evernia prunastriLOTUS Database
Foeniculum vulgareKNApSAcK Database
Gallus gallusFooDB
Lagopus mutaFooDB
Laminaria japonicaKNApSAcK Database
LeporidaeFooDB
Lepus timidusFooDB
Mandragora autumnalisKNApSAcK Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mentha x piperitaFooDB
Musa paradisiacaLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
Ontholestes murinusLOTUS Database
Ophrys sphegodesLOTUS Database
Ophrys spp.KNApSAcK Database
OryctolagusFooDB
Ovis ariesFooDB
Pelargonium vitifoliumLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Polygala senegaLOTUS Database
Prunus aviumFooDB
    • J. P. Mattheis, D. A. Buchanan, and J. K. Fellman Volatile Constituents of Bing Sweet Cherry Frui...
Prunus cerasusFooDB
Psidium guajavaKNApSAcK Database
Saccharina japonicaPlant
Sergia lucensLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Syzygium aromaticumKNApSAcK Database
Tricholoma matsutakeLOTUS Database
Trifolium pratenseLOTUS Database
Trigonella foenum-graecumLOTUS Database
Vaccinium angustifoliumFooDB
    • Lugemwa, F. N., Lwande, W., Bentley, M. D., Mendel, M. J., and Alford, A. R. (1989). Volatiles of...
Vitis viniferaLOTUS Database
Zea maysLOTUS Database
Zea mays L.FooDB
    • Carlos Macku, and Takayuki Shibamoto. Headspace volatile compounds formed from heated corn oil an...
Zingiber miogaLOTUS Database
Zingiber officinaleFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-35 °CNot Available
Boiling Point149.00 to 150.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility4.3 mg/mL at 25 °CNot Available
LogP1.98Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility2.26 g/LALOGPS
logP1.92ALOGPS
logP2.14ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.62 m³·mol⁻¹ChemAxon
Polarizability14.31 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003671
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008055
KNApSAcK IDC00001254
Chemspider ID7760
KEGG Compound IDC08380
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Heptanone
METLIN IDNot Available
PubChem Compound8051
PDB IDNot Available
ChEBI ID5672
Good Scents IDrw1002111
References
General References
  1. Hansson BS, Larsson MC: Receptor neuron responses to potential sex pheromone components in the caddisfly Rhyacophila nubila (Trichoptera: Rhyacophilidae). J Insect Physiol. 1998 Feb;44(2):189-196. doi: 10.1016/s0022-1910(97)00043-7. [PubMed:12769891 ]
  2. Pionnier E, Chabanet C, Mioche L, Le Quere JL, Salles C: 1. In vivo aroma release during eating of a model cheese: relationships with oral parameters. J Agric Food Chem. 2004 Feb 11;52(3):557-64. doi: 10.1021/jf030544v. [PubMed:14759148 ]
  3. Xu F, Schaefer M, Kida I, Schafer J, Liu N, Rothman DL, Hyder F, Restrepo D, Shepherd GM: Simultaneous activation of mouse main and accessory olfactory bulbs by odors or pheromones. J Comp Neurol. 2005 Sep 5;489(4):491-500. doi: 10.1002/cne.20652. [PubMed:16025460 ]
  4. Resconi VC, Campo MM, Montossi F, Ferreira V, Sanudo C, Escudero A: Relationship between odour-active compounds and flavour perception in meat from lambs fed different diets. Meat Sci. 2010 Aug;85(4):700-6. doi: 10.1016/j.meatsci.2010.03.027. Epub 2010 Mar 21. [PubMed:20416794 ]