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Showing NP-Card for 3-penten-2-one (NP0151827)

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Record Information
Version2.0
Created at2022-09-02 08:12:09 UTC
Updated at2022-09-02 08:12:09 UTC
NP-MRD IDNP0151827
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-penten-2-one
DescriptionMethyl propenyl ketone, also known as (3E)-pent-3-en-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'. Methyl propenyl ketone is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-penten-2-one is found in Cichorium endivia and Tamarindus indica. 3-penten-2-one was first documented in 2006 (PMID: 16770722). An enone that is pent-2-ene in which the two methylene hydrogens have been replaced by an oxo group (PMID: 22272978) (PMID: 19246253) (PMID: 22247601) (PMID: 23662795).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0151827 (3-penten-2-one)


  Mrv1533004161519342D          

  6  5  0  0  0  0            999 V2000
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   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
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
M  END
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3D MOL for NP0151827 (3-penten-2-one)

     RDKit          3D

 14 13  0  0  0  0  0  0  0  0999 V2000
    2.4639   -0.2701   -0.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1810    0.4514   -0.4835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0739   -0.1756   -0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2057    0.5086   -0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4844   -0.1592    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2609    1.7047   -0.6255 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0929   -0.0249   -1.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3234   -1.3799   -0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9809   -0.0223    0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1547    1.4707   -0.8106 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0718   -1.2073    0.1731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3501   -0.9846    0.8266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1186    0.5973    0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9228   -0.5086   -0.8683 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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3D SDF for NP0151827 (3-penten-2-one)


  Mrv1533004161519342D          

  6  5  0  0  0  0            999 V2000
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   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
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0151827

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
LABTWGUMFABVFG-UHFFFAOYSA-N

> <FORMULA>
C5H8O

> <MOLECULAR_WEIGHT>
84.118

> <EXACT_MASS>
84.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
9.649396744260637

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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>
-4.453989863515021

> <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>
3-penten-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0151827 (3-penten-2-one)

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PDB for NP0151827 (3-penten-2-one)
HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    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 NP0151827 (3-penten-2-one)
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SMILES for NP0151827 (3-penten-2-one)
CC=CC(C)=O
Download
INCHI for NP0151827 (3-penten-2-one)
InChI=1S/C5H8O/c1-3-4-5(2)6/h3-4H,1-2H3
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View in JSmol
Synonyms
ValueSource
(3E)-Pent-3-en-2-oneChEBI
2-oxo-3-PenteneChEBI
3-Penten-2-oneChEBI
Ethylidene acetoneChEBI
Methyl 1-propenyl ketoneChEBI
Pent-3-en-2-oneChEBI
1-Pentene-3-oneMeSH
Ethyl vinyl ketoneMeSH
PentenoneMeSH
EthylvinylketoneMeSH
Chemical FormulaC5H8O
Average Mass84.1180 Da
Monoisotopic Mass84.05751 Da
IUPAC Namepent-3-en-2-one
Traditional Name3-penten-2-one
CAS Registry NumberNot Available
SMILES
CC=CC(C)=O
InChI Identifier
InChI=1S/C5H8O/c1-3-4-5(2)6/h3-4H,1-2H3
InChI KeyLABTWGUMFABVFG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, 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
    • 

  • Aldehyde
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
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 IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12248  
PDB IDNot Available
ChEBI ID89540  
Good Scents IDNot Available
References
General References
  1. 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  ] 
  2. Blanco MB, Barnes I, Wiesen P: Kinetic investigation of the OH radical and Cl atom initiated degradation of unsaturated ketones at atmospheric pressure and 298 K. J Phys Chem A. 2012 Jun 21;116(24):6033-40. doi: 10.1021/jp2109972. Epub 2012 Feb 10. [PubMed:22272978  ] 
  3. Walker V, Mills GA, Stansbridge EM: 3-Penten-2-one, a novel aldehyde adduct, is a biomarker for increased acetaldehyde in urine. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Mar 15;877(8-9):784-90. doi:  10.1016/j.jchromb.2009.02.017. Epub 2009 Feb 11. [PubMed:19246253  ] 
  4. Kil JS, Son Y, Cheong YK, Kim NH, Jeong HJ, Kwon JW, Lee EJ, Kwon TO, Chung HT, Pae HO: Okanin, a chalcone found in the genus Bidens, and 3-penten-2-one inhibit inducible nitric oxide synthase expression via heme oxygenase-1 induction in RAW264.7 macrophages activated with lipopolysaccharide. J Clin Biochem Nutr. 2012 Jan;50(1):53-8. doi: 10.3164/jcbn.11-30. Epub 2011 Dec  15. [PubMed:22247601  ] 
  5. Kraujalyte V, Leitner E, Venskutonis PR: Characterization of Aronia melanocarpa volatiles by headspace-solid-phase microextraction (HS-SPME), simultaneous distillation/extraction (SDE), and gas chromatography-olfactometry (GC-O) methods. J Agric Food Chem. 2013 May 22;61(20):4728-36. doi: 10.1021/jf400152x. Epub 2013  May 10. [PubMed:23662795  ] 
  6. LOTUS database [Link]