Showing NP-Card for But-3-en-2-one (NP0047026)

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Record Information
Version2.0
Created at2022-03-17 20:33:24 UTC
Updated at2022-03-17 20:33:24 UTC
NP-MRD IDNP0047026
Secondary Accession NumbersNone
Natural Product Identification
Common NameBut-3-en-2-one
Description3-Buten-2-one, also known as 2-butenone or acetyl ethylene, 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, 3-buten-2-one is considered to be an oxygenated hydrocarbon lipid molecule. 3-Buten-2-one, also called methyl vinyl ketone, is the organic compound with the formula CH3CCH=CH2. It is a reactive compound classified as an enone, in fact the simplest example thereof. It is a useful intermediate in the synthesis of other compounds. 3-Buten-2-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3-Buten-2-one has been detected, but not quantified in, several different foods, such as radish (var.), Sour cherries, tamarinds, horseradish, and caraway. This could make 3-buten-2-one a potential biomarker for the consumption of these foods. It is a colorless, flammable, highly toxic liquid with a pungent odor. But-3-en-2-one was first documented in 1977 (PMID: 931562). It is soluble in water and polar organic solvents (PMID: 24068501) (PMID: 24569503) (PMID: 18031883) (PMID: 18031911).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047026 (But-3-en-2-one)

  Mrv1652304172017352D          

  5  4  0  0  0  0            999 V2000
    1.8576   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2866   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0010    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  5  2  0  0  0  0
  2  4  2  0  0  0  0
M  END
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3D MOL for NP0047026 (But-3-en-2-one)

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3D SDF for NP0047026 (But-3-en-2-one)
  Mrv1652304172017352D          

  5  4  0  0  0  0            999 V2000
    1.8576   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2866   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0010    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  5  2  0  0  0  0
  2  4  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047026

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O/c1-3-4(2)5/h3H,1H2,2H3

> <INCHI_KEY>
FUSUHKVFWTUUBE-UHFFFAOYSA-N

> <FORMULA>
C4H6O

> <MOLECULAR_WEIGHT>
70.0898

> <EXACT_MASS>
70.041864814

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
7.552254068796541

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
but-3-en-2-one

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
0.8625728153333332

> <ALOGPS_LOGS>
-0.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.945289804981293

> <JCHEM_PKA_STRONGEST_BASIC>
-4.670010321398548

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
20.8425

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.62e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl vinyl ketone

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047026 (But-3-en-2-one)
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PDB for NP0047026 (But-3-en-2-one)
HEADER    PROTEIN                                 17-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-20         0                                  
HETATM    1  C   UNK     0       3.468  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.801   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.135  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.801   1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       7.469   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2    5                                                       
CONECT    4    2                                                            
CONECT    5    3                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END

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3D PDB for NP0047026 (But-3-en-2-one)
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SMILES for NP0047026 (But-3-en-2-one)
CC(=O)C=C
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INCHI for NP0047026 (But-3-en-2-one)
InChI=1S/C4H6O/c1-3-4(2)5/h3H,1H2,2H3
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View in JSmol
Synonyms
Chemical FormulaC4H6O
Average Mass70.0898 Da
Monoisotopic Mass70.04186 Da
IUPAC Namebut-3-en-2-one
Traditional Namemethyl vinyl ketone
CAS Registry Number78-94-4
SMILES
CC(=O)C=C
InChI Identifier
InChI=1S/C4H6O/c1-3-4(2)5/h3H,1H2,2H3
InChI KeyFUSUHKVFWTUUBE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cinnamomum verumFooDB
Malus pumilaFooDB
Sambucus nigraFooDB
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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.51ALOGPS
logP0.86ChemAxon
logS-0.18ALOGPS
pKa (Strongest Acidic)19.95ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity20.84 m³·mol⁻¹ChemAxon
Polarizability7.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0061873  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007029  
KNApSAcK IDNot Available
Chemspider ID6322  
KEGG Compound IDNot Available
BioCyc IDCPD-8847  
BiGG IDNot Available
Wikipedia LinkMethyl_vinyl_ketone  
METLIN IDNot Available
PubChem Compound6570  
PDB IDNot Available
ChEBI ID48058  
Good Scents IDNot Available
References
General References
  1. Jiang L, Yu HW: An example of enzymatic promiscuity: the Baylis-Hillman reaction catalyzed by a biotin esterase (BioH) from Escherichia coli. Biotechnol Lett. 2014 Jan;36(1):99-103. doi: 10.1007/s10529-013-1329-9. Epub 2013 Sep 26. [PubMed:24068501  ] 
  2. Schone L, Schindelka J, Szeremeta E, Schaefer T, Hoffmann D, Rudzinski KJ, Szmigielski R, Herrmann H: Atmospheric aqueous phase radical chemistry of the isoprene oxidation products methacrolein, methyl vinyl ketone, methacrylic acid and acrylic acid--kinetics and product studies. Phys Chem Chem Phys. 2014 Apr 7;16(13):6257-72. doi: 10.1039/c3cp54859g. [PubMed:24569503  ] 
  3. Unterhalt B, Koehler H: [Halogenated 4-phenyl-3-buten-2-one Oximes (author's transl)]. Arch Pharm (Weinheim). 1977 Oct;310(10):787-92. doi: 10.1002/ardp.19773101005. [PubMed:931562  ] 
  4. Lapczynski A, Lalko J, McGinty D, Bhatia S, Letizia CS, Api AM: Fragrance material review on 4-(3,5,6-trimethyl-3-cyclohexen-1-yl)-3-buten-2-one. Food Chem Toxicol. 2007;45 Suppl 1:S315-7. doi: 10.1016/j.fct.2007.09.035. Epub 2007 Sep 14. [PubMed:18031883  ] 
  5. Lapczynski A, Lalko J, McGinty D, Bhatia S, Letizia CS, Api AM: Fragrance material review on 4-(2,4,6-trimethyl-3-cyclohexen-1-yl)-3-buten-2-one. Food Chem Toxicol. 2007;45 Suppl 1:S311-4. doi: 10.1016/j.fct.2007.09.024. Epub 2007 Sep 14. [PubMed:18031911  ]