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Showing NP-Card for Methyl propenyl ketone (NP0000113)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:40:11 UTC
NP-MRD IDNP0000113
Secondary Accession Numbers
  • NP0073070
Natural Product Identification
Common NameMethyl propenyl ketone
DescriptionMethyl propenyl ketone, also known as (3E)-3-penten-2-one or 2-oxo-3-pentene, belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. Thus, methyl propenyl ketone is considered to be an oxygenated hydrocarbon lipid molecule. Methyl propenyl ketone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Methyl propenyl ketone, with regard to humans, has been found to be associated with several diseases such as nonalcoholic fatty liver disease and ulcerative colitis. Methyl propenyl ketone has also been linked to the inborn metabolic disorder celiac disease. Methyl propenyl ketone is occasionally found as a volatile component of normal human biofluids. It is found as a volatile in the hawthorn fruit upon ripening, and also is part of the scent components of the urine of some animals. Methyl propenyl ketone is a volatile organic compound.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000113 (Methyl propenyl ketone)


  Mrv1652304202019262D          

  6  5  0  0  0  0            999 V2000
   18.2463   -2.9345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5318   -4.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2463   -3.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8171   -3.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9608   -4.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1026   -4.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
M  END
Download

3D MOL for NP0000113 (Methyl propenyl ketone)

HMDB0001184
     RDKit          3D
Methyl propenyl ketone
 14 13  0  0  0  0  0  0  0  0999 V2000
   -2.2669   -0.2441   -0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8055   -0.0289   -0.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1873   -0.3458    0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512   -0.1215    0.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969    0.4576   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593   -0.4558    2.0538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6944    0.7523   -0.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5015   -0.9230   -1.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7094   -0.5562    0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126    0.3963   -1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7952   -0.7725    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870   -0.3318   -0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5985    1.2312   -0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9800    0.9422    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  5 12  1  0
  5 13  1  0
  5 14  1  0
M  END
Download

3D SDF for NP0000113 (Methyl propenyl ketone)


  Mrv1652304202019262D          

  6  5  0  0  0  0            999 V2000
   18.2463   -2.9345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5318   -4.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2463   -3.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8171   -3.7595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9608   -4.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1026   -4.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  3  5  1  0  0  0  0
  4  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000113

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C\C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O/c1-3-4-5(2)6/h3-4H,1-2H3/b4-3+

> <INCHI_KEY>
LABTWGUMFABVFG-ONEGZZNKSA-N

> <FORMULA>
C5H8O

> <MOLECULAR_WEIGHT>
84.1164

> <EXACT_MASS>
84.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
9.649396744260631

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E)-pent-3-en-2-one

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
1.24920781

> <ALOGPS_LOGS>
-0.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.861101976908156

> <JCHEM_PKA_STRONGEST_BASIC>
-4.45398986351502

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
26.516

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(E)-3-penten-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0000113 (Methyl propenyl ketone)

HMDB0001184
     RDKit          3D
Methyl propenyl ketone
 14 13  0  0  0  0  0  0  0  0999 V2000
   -2.2669   -0.2441   -0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8055   -0.0289   -0.3526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1873   -0.3458    0.7744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2512   -0.1215    0.9389 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969    0.4576   -0.1077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7593   -0.4558    2.0538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6944    0.7523   -0.7903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5015   -0.9230   -1.3695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7094   -0.5562    0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2126    0.3963   -1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7952   -0.7725    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4870   -0.3318   -0.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5985    1.2312   -0.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9800    0.9422    0.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  2 10  1  0
  3 11  1  0
  5 12  1  0
  5 13  1  0
  5 14  1  0
M  END
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PDB for NP0000113 (Methyl propenyl ketone)

HEADER    PROTEIN                                 20-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-20         0                                  
HETATM    1  O   UNK     0      34.060  -5.478   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      32.726  -7.788   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      34.060  -7.018   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.392  -7.018   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      35.393  -7.788   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.058  -7.788   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2    3    4                                                       
CONECT    3    1    2    5                                                  
CONECT    4    2    6                                                       
CONECT    5    3                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for NP0000113 (Methyl propenyl ketone)

COMPND    HMDB0001184
HETATM    1  C1  UNL     1      -2.267  -0.244  -0.552  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.805  -0.029  -0.353  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.187  -0.346   0.774  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.251  -0.122   0.939  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.097   0.458  -0.108  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.759  -0.456   2.054  1.00  0.00           O  
HETATM    7  H1  UNL     1      -2.694   0.752  -0.790  1.00  0.00           H  
HETATM    8  H2  UNL     1      -2.501  -0.923  -1.370  1.00  0.00           H  
HETATM    9  H3  UNL     1      -2.709  -0.556   0.429  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.213   0.396  -1.135  1.00  0.00           H  
HETATM   11  H5  UNL     1      -0.795  -0.773   1.553  1.00  0.00           H  
HETATM   12  H6  UNL     1       2.487  -0.332  -0.810  1.00  0.00           H  
HETATM   13  H7  UNL     1       1.598   1.231  -0.705  1.00  0.00           H  
HETATM   14  H8  UNL     1       2.980   0.942   0.366  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    3   10
CONECT    3    4   11
CONECT    4    5    6    6
CONECT    5   12   13   14
END
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SMILES for NP0000113 (Methyl propenyl ketone)

C\C=C\C(C)=O
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INCHI for NP0000113 (Methyl propenyl ketone)

InChI=1S/C5H8O/c1-3-4-5(2)6/h3-4H,1-2H3/b4-3+
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View in JSmol
Synonyms
ValueSource
(3E)-Penten-2-oneChEBI
(e)-3-Penten-2-oneChEBI
(e)-Pent-3-en-2-oneChEBI
trans-3-Penten-2-oneChEBI
(3E)-3-Penten-2-oneHMDB
(3E)-Pent-3-en-2-oneHMDB
2-oxo-3-PenteneHMDB
3-Penten-2-oneHMDB
3-Penten-2-one (methyl vinyl ketone)HMDB
Ethylidene acetoneHMDB
FEMA no. 3417HMDB
Methyl 1-propenyl ketoneHMDB
Pent-3-en-2-oneHMDB
2-oxo-(3E)-PenteneHMDB
Chemical FormulaC5H8O
Average Mass84.1164 Da
Monoisotopic Mass84.05751 Da
IUPAC Name(3E)-pent-3-en-2-one
Traditional Name(E)-3-penten-2-one
CAS Registry Number625-33-2
SMILES
C\C=C\C(C)=O
InChI Identifier
InChI=1S/C5H8O/c1-3-4-5(2)6/h3-4H,1-2H3/b4-3+
InChI KeyLABTWGUMFABVFG-ONEGZZNKSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 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
Cichorium endiviaLOTUS Database
Tamarindus indicaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentEnones
Alternative Parents
Substituents
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point122.5 °CNot Available
Water Solubility46180 mg/l @ 25 °C (est)The Good Scents Company Information System
LogP0.52Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility32.2 g/LALOGPS
logP1.48ALOGPS
logP1.25ChemAxon
logS-0.42ALOGPS
pKa (Strongest Acidic)19.86ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.52 m³·mol⁻¹ChemAxon
Polarizability9.65 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001184
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB112172
KNApSAcK IDNot Available
Chemspider ID553493
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound637920
PDB IDNot Available
ChEBI ID145276
Good Scents IDrw1123851
References
General References
  1. Chen L, Xie B, Yu T: [Identification of volatile compounds of hawthorn by gas chromatography/mass spectrometry (GC/MS)]. Se Pu. 1997 May;15(3):219-21. [PubMed:15739361 ]
  2. Rock F, Mueller S, Weimar U, Rammensee HG, Overath P: Comparative analysis of volatile constituents from mice and their urine. J Chem Ecol. 2006 Jun;32(6):1333-46. Epub 2006 May 31. [PubMed:16770722 ]