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Showing NP-Card for 4-Penten-2-one (NP0047290)

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Record Information
Version1.0
Created at2022-03-17 20:37:43 UTC
Updated at2022-03-17 20:37:44 UTC
NP-MRD IDNP0047290
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Penten-2-one
Description4-Penten-2-one, also known as vinylacetone, 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-penten-2-one is considered to be an oxygenated hydrocarbon lipid molecule. 4-Penten-2-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4-Penten-2-one has been detected, but not quantified in, fruits and tamarinds. This could make 4-penten-2-one a potential biomarker for the consumption of these foods. It was first documented in 1996 (PMID: 11667814). A methyl ketone that is pent-1-ene substituted by an oxo group at position 4.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047290 (4-Penten-2-one)


  Mrv0541 05061306012D          

  6  5  0  0  0  0            999 V2000
    1.2375    2.1434    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
    0.8250    1.4289    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
    0.8250    0.0000    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  2  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
M  END
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3D MOL for NP0047290 (4-Penten-2-one)

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3D SDF for NP0047290 (4-Penten-2-one)

  Mrv0541 05061306012D          

  6  5  0  0  0  0            999 V2000
    1.2375    2.1434    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
    0.8250    1.4289    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
    0.8250    0.0000    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  2  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047290

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O/c1-3-4-5(2)6/h3H,1,4H2,2H3

> <INCHI_KEY>
PNJWIWWMYCMZRO-UHFFFAOYSA-N

> <FORMULA>
C5H8O

> <MOLECULAR_WEIGHT>
84.1164

> <EXACT_MASS>
84.057514878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
9.494209362282714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pent-4-en-2-one

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.9473963339999997

> <ALOGPS_LOGS>
-0.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.88525840835349

> <JCHEM_PKA_STRONGEST_BASIC>
-7.35951587867593

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
25.4668

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pent-4-en-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047290 (4-Penten-2-one)
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PDB for NP0047290 (4-Penten-2-one)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   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    4                                                       
CONECT    4    3    5                                                       
CONECT    5    2    4    6                                                  
CONECT    6    5                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0047290 (4-Penten-2-one)
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SMILES for NP0047290 (4-Penten-2-one)
CC(=O)CC=C
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INCHI for NP0047290 (4-Penten-2-one)
InChI=1S/C5H8O/c1-3-4-5(2)6/h3H,1,4H2,2H3
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View in JSmol
Synonyms
ValueSource
Allyl methyl ketoneHMDB
VinylacetoneHMDB
Chemical FormulaC5H8O
Average Mass84.1164 Da
Monoisotopic Mass84.05751 Da
IUPAC Namepent-4-en-2-one
Traditional Namepent-4-en-2-one
CAS Registry Number13891-87-7
SMILES
CC(=O)CC=C
InChI Identifier
InChI=1S/C5H8O/c1-3-4-5(2)6/h3H,1,4H2,2H3
InChI KeyPNJWIWWMYCMZRO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Tamarindus indicaFooDB
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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.66ALOGPS
logP0.95ChemAxon
logS-0.57ALOGPS
pKa (Strongest Acidic)16.89ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.47 m³·mol⁻¹ChemAxon
Polarizability9.49 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031606  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008242  
KNApSAcK IDNot Available
Chemspider ID75618  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound83797  
PDB IDNot Available
ChEBI ID87508  
Good Scents IDNot Available
References
General References
  1. Nishino H, Nguyen VH, Yoshinaga S, Kurosawa K: Formation of Tetrahydrofuran Derivatives and Acetonylation of Alkenes Using Carbon Radicals Derived from Manganese(III) Oxidation of Diketene. J Org Chem. 1996 Nov 15;61(23):8264-8271. doi: 10.1021/jo960939w. [PubMed:11667814  ]