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Showing NP-Card for 4-Pentenoic acid (NP0337219)

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Record Information
Version2.0
Created at2024-09-11 09:52:45 UTC
Updated at2024-09-11 09:52:45 UTC
NP-MRD IDNP0337219
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Pentenoic acid
Description4-Pentenoic acid, also known as allyl acetic acid or 4-pentenate, belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. 4-Pentenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Pentenoic acid is a cheese, parmesan, and ricotta tasting compound. Outside of the human body,. 4-Pentenoic acid was first documented in 1984 (PMID: 6712730). A pentenoic acid having the double bond at position 4 (PMID: 1936211) (PMID: 2730684) (PMID: 7835402).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337219 (4-Pentenoic acid)


  Mrv1652304272018562D          

  7  6  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
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3D MOL for NP0337219 (4-Pentenoic acid)

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3D SDF for NP0337219 (4-Pentenoic acid)

  Mrv1652304272018562D          

  7  6  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337219

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CCC=C

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O2/c1-2-3-4-5(6)7/h2H,1,3-4H2,(H,6,7)

> <INCHI_KEY>
HVAMZGADVCBITI-UHFFFAOYSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.1158

> <EXACT_MASS>
100.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.343458290193247

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
pent-4-enoic acid

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
1.062339476333333

> <ALOGPS_LOGS>
-0.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.88728129985372

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
26.5167

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.34e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-pentenoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0337219 (4-Pentenoic acid)
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PDB for NP0337219 (4-Pentenoic acid)
HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for NP0337219 (4-Pentenoic acid)
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SMILES for NP0337219 (4-Pentenoic acid)
OC(=O)CCC=C
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INCHI for NP0337219 (4-Pentenoic acid)
InChI=1S/C5H8O2/c1-2-3-4-5(6)7/h2H,1,3-4H2,(H,6,7)
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Synonyms
ValueSource
3-Vinylpropionic acidChEBI
4-Penten-1-Oic acidChEBI
4-Pentenic acidChEBI
4-PentensaeureChEBI
Allyl acetic acidChEBI
Allylacetic acidChEBI
AllylessigsaeureChEBI
Delta(4)-Pentenoic acidChEBI
3-VinylpropionateGenerator
4-Penten-1-OateGenerator
4-PentenateGenerator
Allyl acetateGenerator
AllylacetateGenerator
delta(4)-PentenoateGenerator
Δ(4)-pentenoateGenerator
Δ(4)-pentenoic acidGenerator
4-PentenoateGenerator
3-Butene-1-carboxylic acidHMDB
Delta4-Pentenoic acidHMDB
FEMA 2843HMDB
Pent-4-enoic acidHMDB
4-Pentenoic acid, sodium saltHMDB
Pent-4-enoateHMDB
4-Pentenoic acid, potassium saltHMDB
4-Pentenoic acidChEBI
Chemical FormulaC5H8O2
Average Mass100.1158 Da
Monoisotopic Mass100.05243 Da
IUPAC Namepent-4-enoic acid
Traditional Name4-pentenoic acid
CAS Registry NumberNot Available
SMILES
OC(=O)CCC=C
InChI Identifier
InChI=1S/C5H8O2/c1-2-3-4-5(6)7/h2H,1,3-4H2,(H,6,7)
InChI KeyHVAMZGADVCBITI-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty acids and conjugates  
Direct ParentStraight chain fatty acids  
Alternative Parents
Substituents
  • Unsaturated fatty acid
    • 

  • Straight chain fatty acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP0.87ALOGPS
logP1.06ChemAxon
logS-0.2ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.52 m³·mol⁻¹ChemAxon
Polarizability10.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031602  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008235  
KNApSAcK IDNot Available
Chemspider ID55085  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound61138  
PDB IDNot Available
ChEBI ID35936  
Good Scents IDNot Available
References
General References
  1. Hidaka T, Inokuchi T, Nakamura Y, Kotegawa M, Sugiyama M, Ogura R: Prevention of 4-pentenoic acid-induced liver injury in rats by 16,16-dimethyl PGE2. Exp Mol Pathol. 1991 Oct;55(2):135-42. doi: 10.1016/0014-4800(91)90048-3. [PubMed:1936211  ] 
  2. Hart MA, Swisher JA, Caspers ML: Alterations in plasma amino acids and hepatic enzymes in the 4-pentenoic acid model of Reye's syndrome. Biochem Pharmacol. 1989 May 15;38(10):1696-8. doi: 10.1016/0006-2952(89)90320-1. [PubMed:2730684  ] 
  3. Thayer WS: Inhibition of mitochondrial fatty acid oxidation in pentenoic acid-induced fatty liver. A possible model for Reye's syndrome. Biochem Pharmacol. 1984 Apr 15;33(8):1187-94. doi: 10.1016/0006-2952(84)90169-2. [PubMed:6712730  ] 
  4. Hurst JS, Bazan HE, Balazy M: The incorporation and release of 12(S)-hydroxyeicosatetraenoic acid and its major metabolite, 8(S)-hydroxyhexadecatrienoic acid, from rabbit corneal lipids. Exp Eye Res. 1994 Jul;59(1):97-105. doi: 10.1006/exer.1994.1085. [PubMed:7835402  ]