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Showing NP-Card for delta-valerolactone (NP0213348)

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Record Information
Version1.0
Created at2022-09-05 12:18:35 UTC
Updated at2022-09-05 12:18:35 UTC
NP-MRD IDNP0213348
Secondary Accession NumbersNone
Natural Product Identification
Common Namedelta-valerolactone
Description5-Valerolactone belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. delta-valerolactone is found in Aspalathus linearis and Clerodendrum mandarinorum. It was first documented in 2005 (PMID: 16134088). 5-Valerolactone is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 18324833).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0213348 (delta-valerolactone)


  Mrv1533004241508262D          

  7  7  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
M  END
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3D MOL for NP0213348 (delta-valerolactone)

     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
    2.5767    0.9700    0.7303 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4067    0.6634    0.4541 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9194   -0.7032    0.7085 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0628   -1.0497   -0.5108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1098   -0.1229   -0.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9009    1.2275    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4997    1.5409   -0.0926 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7128   -1.4386    0.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2427   -0.7422    1.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7343   -0.9260   -1.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2209   -2.1164   -0.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3072    0.0500   -1.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9732   -0.6292   -0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4680    1.9890   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1752    1.2873    1.0777 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  2  1  0
  3  8  1  0
  3  9  1  0
  4 10  1  0
  4 11  1  0
  5 12  1  0
  5 13  1  0
  6 14  1  0
  6 15  1  0
M  END
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3D SDF for NP0213348 (delta-valerolactone)


  Mrv1533004241508262D          

  7  7  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213348

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1CCCCO1

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O2/c6-5-3-1-2-4-7-5/h1-4H2

> <INCHI_KEY>
OZJPLYNZGCXSJM-UHFFFAOYSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.117

> <EXACT_MASS>
100.052429498

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.13461628715531

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
oxan-2-one

> <ALOGPS_LOGP>
0.31

> <JCHEM_LOGP>
0.5941199706666667

> <ALOGPS_LOGS>
-0.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.032743010701426

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
24.9091

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.54e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
delta-valerolactone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0213348 (delta-valerolactone)

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PDB for NP0213348 (delta-valerolactone)
HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   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    6    2                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0213348 (delta-valerolactone)
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SMILES for NP0213348 (delta-valerolactone)
O=C1CCCCO1
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INCHI for NP0213348 (delta-valerolactone)
InChI=1S/C5H8O2/c6-5-3-1-2-4-7-5/h1-4H2
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View in JSmol
Synonyms
ValueSource
delta-ValerolactoneChEBI
gamma-ValerolactoneKegg
Δ-valerolactoneGenerator
g-ValerolactoneGenerator
Γ-valerolactoneGenerator
delta-ValerothiolactoneMeSH
Chemical FormulaC5H8O2
Average Mass100.1170 Da
Monoisotopic Mass100.05243 Da
IUPAC Nameoxan-2-one
Traditional Namedelta-valerolactone
CAS Registry NumberNot Available
SMILES
O=C1CCCCO1
InChI Identifier
InChI=1S/C5H8O2/c6-5-3-1-2-4-7-5/h1-4H2
InChI KeyOZJPLYNZGCXSJM-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
Aspalathus linearisLOTUS Database
Clerodendrum mandarinorumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactones  
Sub ClassDelta valerolactones  
Direct ParentDelta valerolactones  
Alternative Parents
Substituents
  • Delta_valerolactone
    • 

  • Delta valerolactone
    • 

  • Oxane
    • 

  • 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 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
logP0.31ALOGPS
logP0.59ChemAxon
logS-0.02ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity24.91 m³·mol⁻¹ChemAxon
Polarizability10.13 ųChemAxon
Number of Rings1ChemAxon
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 IDC02240  
BioCyc ID5-VALEROLACTONE  
BiGG IDNot Available
Wikipedia LinkDelta-Valerolactone  
METLIN IDNot Available
PubChem Compound10953  
PDB IDNot Available
ChEBI ID16545  
Good Scents IDNot Available
References
General References
  1. Yang J, Jia L, Hao Q, Li Y, Li Q, Fang Q, Cao A: New biodegradable amphiphilic block copolymers of epsilon-caprolactone and delta-valerolactone catalyzed by novel aluminum metal complexes. II. Micellization and solution to gel transition. Macromol Biosci. 2005 Sep 16;5(9):896-903. doi: 10.1002/mabi.200500096. [PubMed:16134088  ] 
  2. Houk KN, Jabbari A, Hall HK Jr, Aleman C: Why delta-valerolactone polymerizes and gamma-butyrolactone does not. J Org Chem. 2008 Apr 4;73(7):2674-8. doi: 10.1021/jo702567v. Epub 2008 Mar 7. [PubMed:18324833  ] 
  3. LOTUS database [Link]