Showing NP-Card for gamma-nonalactone (NP0207992)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Show more...Show more...
Record Information
Version2.0
Created at2022-09-05 04:49:35 UTC
Updated at2022-09-05 04:49:35 UTC
NP-MRD IDNP0207992
Secondary Accession NumbersNone
Natural Product Identification
Common Namegamma-nonalactone
DescriptionDihydro-5-pentyl-2(3H)-furanone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, dihydro-5-pentyl-2(3H)-furanone is considered to be a fatty ester lipid molecule. gamma-nonalactone is found in Angelica dahurica, Aspalathus linearis, Carpesium abrotanoides, Citrullus lanatus, Fusarium poae, Glycyrrhiza glabra, Gossypium hirsutum, Hamamelis virginiana, Mangifera indica, Opuntia ficus-indica, Polygala senega, Prunus dulcis, Trigonella foenum-graecum and Zea mays. Dihydro-5-pentyl-2(3H)-furanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0207992 (gamma-nonalactone)

  Mrv0541 02241215282D          

 11 11  0  0  0  0            999 V2000
   -1.1955   -1.8550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357   -1.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886   -1.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886   -0.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5357    0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0409    1.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7833    1.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886    1.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1955    1.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357   -0.5353    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 11  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
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
Download

3D MOL for NP0207992 (gamma-nonalactone)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
   -3.7489    0.1850   -0.1331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8032   -0.9942   -0.2101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3845   -0.4872   -0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0212    0.4294    0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3345    1.0321    0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4521    0.0170    0.4879 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7711    0.7912    0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6666   -0.3077   -0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7459   -0.9422   -1.1659 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0543   -1.5811   -2.1888 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4540   -0.6979   -0.7211 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6935    0.6774    0.8757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200    0.9479   -0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7852   -0.2084   -0.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7746   -1.5057    0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1476   -1.6984   -0.9701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3900    0.0076   -1.4820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7616   -1.4071   -0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059   -0.1050    1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7585    1.2660    0.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4977    1.6439    1.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3596    1.7161   -0.3217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4570   -0.6150    1.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6552    1.6237   -0.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1301    1.1255    1.3579 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5746    0.1037   -0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8421   -1.0166    0.6269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  1
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
M  END
Download

3D SDF for NP0207992 (gamma-nonalactone)

  Mrv0541 02241215282D          

 11 11  0  0  0  0            999 V2000
   -1.1955   -1.8550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357   -1.3603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886   -1.6080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886   -0.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5357    0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0409    1.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7833    1.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2886    1.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1955    1.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357   -0.5353    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 11  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
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0207992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1CCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C9H16O2/c1-2-3-4-5-8-6-7-9(10)11-8/h8H,2-7H2,1H3

> <INCHI_KEY>
OALYTRUKMRCXNH-UHFFFAOYSA-N

> <FORMULA>
C9H16O2

> <MOLECULAR_WEIGHT>
156.2221

> <EXACT_MASS>
156.115029756

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.327496484601895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-pentyloxolan-2-one

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.422354720333333

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.042552424460948

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
43.0539

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.79e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-pentyloxolan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0207992 (gamma-nonalactone)

Download
PDB for NP0207992 (gamma-nonalactone)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -2.232  -3.463   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.000  -2.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.539  -3.002   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.308  -1.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.539  -0.538   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.000   0.846   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.076   2.078   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.462   2.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.539   3.308   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.232   3.463   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.000  -0.999   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    2    5                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

Download
3D PDB for NP0207992 (gamma-nonalactone)
Download
SMILES for NP0207992 (gamma-nonalactone)
CCCCCC1CCC(=O)O1
Download
INCHI for NP0207992 (gamma-nonalactone)
InChI=1S/C9H16O2/c1-2-3-4-5-8-6-7-9(10)11-8/h8H,2-7H2,1H3
Download
View in JSmol
Synonyms
ValueSource
g-NonanolideGenerator
Γ-nonanolideGenerator
Chemical FormulaC9H16O2
Average Mass156.2221 Da
Monoisotopic Mass156.11503 Da
IUPAC Name5-pentyloxolan-2-one
Traditional Name5-pentyloxolan-2-one
CAS Registry NumberNot Available
SMILES
CCCCCC1CCC(=O)O1
InChI Identifier
InChI=1S/C9H16O2/c1-2-3-4-5-8-6-7-9(10)11-8/h8H,2-7H2,1H3
InChI KeyOALYTRUKMRCXNH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactones  
Sub ClassGamma butyrolactones  
Direct ParentGamma butyrolactones  
Alternative Parents
Substituents
  • Gamma butyrolactone
    • 

  • Tetrahydrofuran
    • 

  • 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
logP2.41ALOGPS
logP2.42ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.05 m³·mol⁻¹ChemAxon
Polarizability18.33 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031531  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008138  
KNApSAcK IDC00001318  
Chemspider ID7424  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7710  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]