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Showing NP-Card for 4-Heptanone (NP0000303)

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Record Information
Version1.0
Created at2006-08-24 12:19:01 UTC
Updated at2021-08-19 23:58:01 UTC
NP-MRD IDNP0000303
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Heptanone
Description4-Heptanone, also known as dipropyl ketone or 4-oxoheptane, 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, 4-heptanone is considered to be an oxygenated hydrocarbon lipid molecule. 4-Heptanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 4-Heptanone is a sweet, cheese, and cognac tasting compound. With regards to humans, 4-Heptanone has been found to be associated with several diseases such as kidney disease, perillyl alcohol administration for cancer treatment, pervasive developmental disorder not otherwise specified, and autism; 4-heptanone has also been linked to the inborn metabolic disorder celiac disease.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000303 (4-Heptanone)


  Mrv1652305261923592D          

  8  7  0  0  0  0            999 V2000
   19.3228  -14.9950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0372  -13.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6083  -13.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3228  -14.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7517  -14.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8937  -14.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4662  -13.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1793  -13.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
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3D MOL for NP0000303 (4-Heptanone)

HMDB0004814
     RDKit          3D
4-Heptanone
 22 21  0  0  0  0  0  0  0  0999 V2000
   -2.5969    0.7473    0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3790   -0.7466    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1174   -1.0513   -0.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0912   -0.4797    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0888    0.1582    1.1023 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3922   -0.7177   -0.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5370   -0.0787    0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    1.4066    0.2354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    1.3257    0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8759    0.9348    1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4532    1.1019   -0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386   -1.2765    1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2255   -1.1358   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9650   -2.1554   -0.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1620   -0.6229   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3704   -0.1811   -1.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5215   -1.7960   -0.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4761   -0.3019   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5115   -0.5145    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2448    1.7528    1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2892    1.6839   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985    1.9468   -0.2528 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  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
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
M  END
Download

3D SDF for NP0000303 (4-Heptanone)


  Mrv1652305261923592D          

  8  7  0  0  0  0            999 V2000
   19.3228  -14.9950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0372  -13.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6083  -13.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3228  -14.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7517  -14.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8937  -14.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4662  -13.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1793  -13.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000303

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)CCC

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

> <INCHI_KEY>
HCFAJYNVAYBARA-UHFFFAOYSA-N

> <FORMULA>
C7H14O

> <MOLECULAR_WEIGHT>
114.1855

> <EXACT_MASS>
114.10446507

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.214020322763455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
heptan-4-one

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
2.3964888323333335

> <ALOGPS_LOGS>
-1.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.346622397493137

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
34.6506

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propyl ketone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000303 (4-Heptanone)

HMDB0004814
     RDKit          3D
4-Heptanone
 22 21  0  0  0  0  0  0  0  0999 V2000
   -2.5969    0.7473    0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3790   -0.7466    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1174   -1.0513   -0.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0912   -0.4797    0.0743 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0888    0.1582    1.1023 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3922   -0.7177   -0.6020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5370   -0.0787    0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2612    1.4066    0.2354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6689    1.3257    0.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8759    0.9348    1.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4532    1.1019   -0.2937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4386   -1.2765    1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2255   -1.1358   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9650   -2.1554   -0.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1620   -0.6229   -1.5953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3704   -0.1811   -1.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5215   -1.7960   -0.7249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4761   -0.3019   -0.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5115   -0.5145    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2448    1.7528    1.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2892    1.6839   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0985    1.9468   -0.2528 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  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
  6 16  1  0
  6 17  1  0
  7 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
  8 22  1  0
M  END
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PDB for NP0000303 (4-Heptanone)

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  O   UNK     0      36.069 -27.991   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      37.403 -25.680   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      34.735 -25.680   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      36.069 -26.450   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      38.737 -26.450   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      33.402 -26.450   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      40.070 -25.680   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.068 -25.680   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    4    5                                                       
CONECT    3    4    6                                                       
CONECT    4    1    2    3                                                  
CONECT    5    2    7                                                       
CONECT    6    3    8                                                       
CONECT    7    5                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for NP0000303 (4-Heptanone)

COMPND    HMDB0004814
HETATM    1  C1  UNL     1      -2.597   0.747   0.320  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.379  -0.747   0.201  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.117  -1.051  -0.574  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.091  -0.480   0.074  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.089   0.158   1.102  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.392  -0.718  -0.602  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.537  -0.079   0.168  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.261   1.407   0.235  1.00  0.00           C  
HETATM    9  H1  UNL     1      -1.669   1.326   0.097  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.876   0.935   1.395  1.00  0.00           H  
HETATM   11  H3  UNL     1      -3.453   1.102  -0.294  1.00  0.00           H  
HETATM   12  H4  UNL     1      -2.439  -1.277   1.149  1.00  0.00           H  
HETATM   13  H5  UNL     1      -3.225  -1.136  -0.431  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.965  -2.155  -0.594  1.00  0.00           H  
HETATM   15  H7  UNL     1      -1.162  -0.623  -1.595  1.00  0.00           H  
HETATM   16  H8  UNL     1       1.370  -0.181  -1.596  1.00  0.00           H  
HETATM   17  H9  UNL     1       1.521  -1.796  -0.725  1.00  0.00           H  
HETATM   18  H10 UNL     1       3.476  -0.302  -0.351  1.00  0.00           H  
HETATM   19  H11 UNL     1       2.511  -0.514   1.190  1.00  0.00           H  
HETATM   20  H12 UNL     1       2.245   1.753   1.296  1.00  0.00           H  
HETATM   21  H13 UNL     1       1.289   1.684  -0.213  1.00  0.00           H  
HETATM   22  H14 UNL     1       3.099   1.947  -0.253  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3   12   13
CONECT    3    4   14   15
CONECT    4    5    5    6
CONECT    6    7   16   17
CONECT    7    8   18   19
CONECT    8   20   21   22
END
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SMILES for NP0000303 (4-Heptanone)

CCCC(=O)CCC
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INCHI for NP0000303 (4-Heptanone)

InChI=1S/C7H14O/c1-3-5-7(8)6-4-2/h3-6H2,1-2H3
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View in JSmol
Synonyms
ValueSource
4-OxoheptaneChEBI
ButyroneChEBI
Di-N-propyl ketoneChEBI
Dipropyl ketoneChEBI
Heptan-4-oneChEBI
Propyl ketoneChEBI
4-HeptanoneMeSH
Chemical FormulaC7H14O
Average Mass114.1855 Da
Monoisotopic Mass114.10447 Da
IUPAC Nameheptan-4-one
Traditional Namepropyl ketone
CAS Registry Number123-19-3
SMILES
CCCC(=O)CCC
InChI Identifier
InChI=1S/C7H14O/c1-3-5-7(8)6-4-2/h3-6H2,1-2H3
InChI KeyHCFAJYNVAYBARA-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)Varshavi.d262021-09-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Varshavi.d262021-09-05View 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
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-08-03View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Aspalathus linearisLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capillipedium parviflorumKNApSAcK Database
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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-34 °CNot Available
Boiling Point144.00 to 145.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility3.2 mg/mL at 25 °CNot Available
LogP1.996 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility4.51 g/LALOGPS
logP2.06ALOGPS
logP2.4ChemAxon
logS-1.4ALOGPS
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.65 m³·mol⁻¹ChemAxon
Polarizability14.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004814
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008059
KNApSAcK IDC00035501
Chemspider ID28986
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Heptanone
METLIN ID7078
PubChem Compound31246
PDB IDNot Available
ChEBI ID89484
Good Scents IDrw1025681
References
General References
  1. Wahl HG, Hoffmann A, Luft D, Liebich HM: Analysis of volatile organic compounds in human urine by headspace gas chromatography-mass spectrometry with a multipurpose sampler. J Chromatogr A. 1999 Jun 25;847(1-2):117-25. [PubMed:10431355 ]
  2. Statheropoulos M, Sianos E, Agapiou A, Georgiadou A, Pappa A, Tzamtzis N, Giotaki H, Papageorgiou C, Kolostoumbis D: Preliminary investigation of using volatile organic compounds from human expired air, blood and urine for locating entrapped people in earthquakes. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):112-7. [PubMed:15996539 ]
  3. Walker V, Mills GA: Urine 4-heptanone: a beta-oxidation product of 2-ethylhexanoic acid from plasticisers. Clin Chim Acta. 2001 Apr;306(1-2):51-61. [PubMed:11282094 ]
  4. Dayrit FM, Ninonuevo MR: Development of an analytical method for 3-monochloropropane-1,2-diol in soy sauce using 4-heptanone as derivatizing agent. Food Addit Contam. 2004 Mar;21(3):204-9. doi: 10.1080/02652030310001656352. [PubMed:15195467 ]
  5. Wahl HG, Hong Q, Hildenbrand S, Risler T, Luft D, Liebich H: 4-Heptanone is a metabolite of the plasticizer di(2-ethylhexyl) phthalate (DEHP) in haemodialysis patients. Nephrol Dial Transplant. 2004 Oct;19(10):2576-83. doi: 10.1093/ndt/gfh425. Epub 2004 Jul 27. [PubMed:15280519 ]