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Showing NP-Card for massoia lactone (NP0250030)

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Record Information
Version2.0
Created at2022-09-07 12:45:28 UTC
Updated at2022-09-07 12:45:28 UTC
NP-MRD IDNP0250030
Secondary Accession NumbersNone
Natural Product Identification
Common Namemassoia lactone
Description5,6-Dihydro-6-pentyl-2H-pyran-2-one, also known as 5-hydroxy-2-decenoic acid D-lactone or C-10 massoia lactone, 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. 5,6-Dihydro-6-pentyl-2H-pyran-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). 5,6-Dihydro-6-pentyl-2H-pyran-2-one is a sweet, coconut, and creamy tasting compound. Outside of the human body, 5,6-Dihydro-6-pentyl-2H-pyran-2-one has been detected, but not quantified in, fruits. massoia lactone is found in Fusarium solani. This could make 5,6-dihydro-6-pentyl-2H-pyran-2-one a potential biomarker for the consumption of these foods.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0250030 (massoia lactone)


  Mrv0541 02241215112D          

 12 12  0  0  0  0            999 V2000
   -1.0309    1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -0.0004    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 12  1  0  0  0  0
  3  4  2  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
  6 12  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
 10 11  1  0  0  0  0
M  END
Download

3D MOL for NP0250030 (massoia lactone)

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
   -3.6945    0.1563    0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939   -0.1874   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214   -0.9746   -0.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9090   -0.1749    0.0710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4198   -0.8880    0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4371    0.0483    0.6777 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8097   -0.5227    0.7125 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7250    0.0089   -0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5031    1.0452   -1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2353    1.7492   -0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9753    2.7648   -1.6239 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3347    1.2849    0.0363 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1713    1.0810    1.3014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7848    0.4450    0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6011   -0.6739    1.6624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723    0.7492   -1.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1115   -0.7593   -0.9751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7842   -1.1341   -1.5986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1104   -1.9726   -0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0907    0.1139    1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7800    0.7604   -0.5343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173   -1.1660   -0.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3238   -1.8031    0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664    0.1918    1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8294   -1.6439    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2643   -0.3138    1.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6801   -0.5101   -0.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2041    1.4195   -1.7978 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  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12  6  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  1
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
M  END
Download

3D SDF for NP0250030 (massoia lactone)


  Mrv0541 02241215112D          

 12 12  0  0  0  0            999 V2000
   -1.0309    1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0309   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1133   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708   -0.0004    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 12  1  0  0  0  0
  3  4  2  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
  6 12  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
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0250030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1CC=CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O2/c1-2-3-4-6-9-7-5-8-10(11)12-9/h5,8-9H,2-4,6-7H2,1H3

> <INCHI_KEY>
NEDIAPMWNCQWNW-UHFFFAOYSA-N

> <FORMULA>
C10H16O2

> <MOLECULAR_WEIGHT>
168.2328

> <EXACT_MASS>
168.115029756

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.59677997497928

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-pentyl-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
3.098080208333333

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.27798894158561

> <JCHEM_PKA_STRONGEST_BASIC>
-6.800379144826258

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
48.7482

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
massoia lactone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0250030 (massoia lactone)

Download
PDB for NP0250030 (massoia lactone)
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      -1.924   2.309   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.924   0.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.310  -0.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.310  -1.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.924  -2.309   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.692  -1.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.692  -2.309   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.078  -1.539   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.078  -0.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.310   0.769   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.310   2.309   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.692  -0.001   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    2    6                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0250030 (massoia lactone)
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SMILES for NP0250030 (massoia lactone)
CCCCCC1CC=CC(=O)O1
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INCHI for NP0250030 (massoia lactone)
InChI=1S/C10H16O2/c1-2-3-4-6-9-7-5-8-10(11)12-9/h5,8-9H,2-4,6-7H2,1H3
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View in JSmol
Synonyms
ValueSource
(R)-5,6-Dihydro-6-pentyl-2H-pyran-2-oneHMDB
2-Decen-5-olideHMDB
5,6-Dihydro-6-pentyl-(6R)-2H-pyran-2-oneHMDB
5,6-Dihydro-6-pentyl-(R)-2H-pyran-2-oneHMDB
5,6-Dihydro-6-pentyl-(theta)-2H-pyran-2-oneHMDB
5-Hydroxy-2-decenoic acid D-lactoneHMDB
5-Hydroxy-2-decenoic acid delta-lactoneHMDB
5-Hydroxy-2-decenoic acid lactoneHMDB
5-Hydroxy-2-decenoic acid laquo deltaraquo -lactoneHMDB
5-Hydroxy-2-decenoic acid, delta-lactoneHMDB
5-Hydroxy-2-decenoic acid, lactoneHMDB
C-10 Massoia lactoneHMDB
CocolactoneHMDB
FEMA 3744HMDB
Massoia lactoneHMDB
MassoilactoneHMDB
Massoy lactoneHMDB
Chemical FormulaC10H16O2
Average Mass168.2328 Da
Monoisotopic Mass168.11503 Da
IUPAC Name6-pentyl-5,6-dihydro-2H-pyran-2-one
Traditional Namemassoia lactone
CAS Registry NumberNot Available
SMILES
CCCCCC1CC=CC(=O)O1
InChI Identifier
InChI=1S/C10H16O2/c1-2-3-4-6-9-7-5-8-10(11)12-9/h5,8-9H,2-4,6-7H2,1H3
InChI KeyNEDIAPMWNCQWNW-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
Fusarium solaniLOTUS Database
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
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate 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
logP3.12ALOGPS
logP3.1ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)17.28ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity48.75 m³·mol⁻¹ChemAxon
Polarizability19.6 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034452  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012860  
KNApSAcK IDNot Available
Chemspider ID36500  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound39914  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]