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Showing NP-Card for 5-Hydroxy-4-pentenoic acid d-lactone (NP0336925)

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Record Information
Version2.0
Created at2024-09-11 08:27:03 UTC
Updated at2024-09-11 08:27:04 UTC
NP-MRD IDNP0336925
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Hydroxy-4-pentenoic acid d-lactone
Description5-Hydroxy-4-pentenoic acid d-lactone, also known as 3,4-dihydro-2H-pyran-2-one or 4,5-dehydrovalerolactone, belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. 5-Hydroxy-4-pentenoic acid d-lactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 5-Hydroxy-4-pentenoic acid d-lactone has been detected, but not quantified in, nuts. This could make 5-hydroxy-4-pentenoic acid D-lactone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336925 (5-Hydroxy-4-pentenoic acid d-lactone)


  Mrv0541 05061311392D          

  7  7  0  0  0  0            999 V2000
   -0.7703   -0.8246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1981    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9128    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9128   -0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1981   -0.8246    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
  2  7  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
  6  7  1  0  0  0  0
M  END
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3D MOL for NP0336925 (5-Hydroxy-4-pentenoic acid d-lactone)

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3D SDF for NP0336925 (5-Hydroxy-4-pentenoic acid d-lactone)

  Mrv0541 05061311392D          

  7  7  0  0  0  0            999 V2000
   -0.7703   -0.8246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835   -0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4835    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1981    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9128    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9128   -0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1981   -0.8246    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
  2  7  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
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336925

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CCC=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O2/c6-5-3-1-2-4-7-5/h2,4H,1,3H2

> <INCHI_KEY>
VEFDLKXOSOFUIN-UHFFFAOYSA-N

> <FORMULA>
C5H6O2

> <MOLECULAR_WEIGHT>
98.0999

> <EXACT_MASS>
98.036779436

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
9.329548385970492

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
0.63

> <JCHEM_LOGP>
0.6060990156666666

> <ALOGPS_LOGS>
0.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.15911865169973

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
25.0022

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0336925 (5-Hydroxy-4-pentenoic acid d-lactone)
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PDB for NP0336925 (5-Hydroxy-4-pentenoic acid d-lactone)
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  O   UNK     0      -1.438  -1.539   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.769  -0.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.769   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.103   1.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.437   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.437  -0.769   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.103  -1.539   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    2    6                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0336925 (5-Hydroxy-4-pentenoic acid d-lactone)
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SMILES for NP0336925 (5-Hydroxy-4-pentenoic acid d-lactone)
O=C1CCC=CO1
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INCHI for NP0336925 (5-Hydroxy-4-pentenoic acid d-lactone)
InChI=1S/C5H6O2/c6-5-3-1-2-4-7-5/h2,4H,1,3H2
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Synonyms
ValueSource
5-Hydroxy-4-pentenoate D-lactoneGenerator
3,4-Dihydro-2H-pyran-2-oneHMDB
4,5-DehydrovalerolactoneHMDB
Chemical FormulaC5H6O2
Average Mass98.0999 Da
Monoisotopic Mass98.03678 Da
IUPAC Name3,4-dihydro-2H-pyran-2-one
Traditional Name3,4-dihydropyran-2-one
CAS Registry NumberNot Available
SMILES
O=C1CCC=CO1
InChI Identifier
InChI=1S/C5H6O2/c6-5-3-1-2-4-7-5/h2,4H,1,3H2
InChI KeyVEFDLKXOSOFUIN-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 dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentDihydropyranones  
Alternative Parents
Substituents
  • Dihydropyranone
    • 

  • Enol ester
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP0.63ALOGPS
logP0.61ChemAxon
logS0.05ALOGPS
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25 m³·mol⁻¹ChemAxon
Polarizability9.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040145  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019842  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound147020  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available