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Showing NP-Card for 2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone (NP0337326)

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Record Information
Version2.0
Created at2024-09-11 10:20:40 UTC
Updated at2024-09-11 10:20:40 UTC
NP-MRD IDNP0337326
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone
Description 2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone was first documented in 2017 (PMID: 28573856). Based on a literature review a significant number of articles have been published on Wine lactone (PMID: 38334101) (PMID: 34547201) (PMID: 33720279) (PMID: 31502833) (PMID: 30813719) (PMID: 29889522).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0337326 (2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone)


  Mrv2104 05262312522D          

 12 13  0  0  0  0            999 V2000
   -1.3610    0.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610   -0.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6467   -0.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660   -0.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    0.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6467    1.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6467   -1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776   -1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776   -0.5339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6467    1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3610   -1.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  2  0  0  0  0
M  END
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3D MOL for NP0337326 (2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone)

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3D SDF for NP0337326 (2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone)

  Mrv2104 05262312522D          

 12 13  0  0  0  0            999 V2000
   -1.3610    0.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3610   -0.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6467   -0.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660   -0.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0660    0.7046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6467    1.1160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6467   -1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776   -1.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7776   -0.5339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6467    1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3610   -1.9417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2302   -1.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  2  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0337326

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CCC(C)=CC2OC1=O

> <INCHI_IDENTIFIER>
InChI=1/C10H14O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h5,7-9H,3-4H2,1-2H3

> <INCHI_KEY>
NQWBFQXRASPNLB-UHFFFAOYNA-N

> <FORMULA>
C10H14O2

> <MOLECULAR_WEIGHT>
166.22

> <EXACT_MASS>
166.099379691

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
18.197077839892025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-one

> <JCHEM_LOGP>
2.014797667333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.092979903000659

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
46.3404

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
wine lactone

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0337326 (2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone)
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PDB for NP0337326 (2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -2.541   1.315   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.541  -0.226   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.207  -0.997   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.123  -0.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.123   1.315   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.207   2.083   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.207  -2.535   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.452  -2.535   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.452  -0.997   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.207   3.625   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.541  -3.625   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.296  -3.625   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5   10                                                  
CONECT    7    3    8   12                                                  
CONECT    8    7    9   11                                                  
CONECT    9    4    8                                                       
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12    7                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0337326 (2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone)
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SMILES for NP0337326 (2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone)
CC1C2CCC(C)=CC2OC1=O
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INCHI for NP0337326 (2-(2-Hydroxy-4-methyl-3-cyclohexenyl)propionic acid gamma-lactone)
InChI=1/C10H14O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h5,7-9H,3-4H2,1-2H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H14O2
Average Mass166.2200 Da
Monoisotopic Mass166.09938 Da
IUPAC Name3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-one
Traditional Namewine lactone
CAS Registry NumberNot Available
SMILES
CC1C2CCC(C)=CC2OC1=O
InChI Identifier
InChI=1/C10H14O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h5,7-9H,3-4H2,1-2H3
InChI KeyNQWBFQXRASPNLB-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
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
logP2.01ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.34 m³·mol⁻¹ChemAxon
Polarizability18.2 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
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 IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkWine lactone  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Peng B, Ran J, Li Y, Tang M, Xiao H, Shi S, Ning Y, Dark A, Li J, Guan X, Song Z: Site-Directed Mutagenesis of VvCYP76F14 (Cytochrome P450) Unveils Its Potential for Selection in Wine Grape Varieties Linked to the Development of Wine Bouquet. J Agric Food Chem. 2024 Feb 21;72(7):3683-3694. doi: 10.1021/acs.jafc.3c09083.  Epub 2024 Feb 9. [PubMed:38334101  ] 
  2. Dein M, Kerley T, Munafo JP Jr: Characterization of Odorants in a 10-Year-Old Riesling Wine. J Agric Food Chem. 2021 Sep 29;69(38):11372-11381. doi: 10.1021/acs.jafc.1c04196.  Epub 2021 Sep 21. [PubMed:34547201  ] 
  3. Ohkubo Y, Masuda Y, Ogura Y, Takikawa H, Watanabe H: Concise enantioselective synthesis of wine lactone via intramolecular Diels-Alder reaction. Biosci Biotechnol Biochem. 2021 May 25;85(6):1390-1394. doi: 10.1093/bbb/zbab045. [PubMed:33720279  ] 
  4. Touge T, Sakaguchi K, Tamaki N, Nara H, Yokozawa T, Matsumura K, Kayaki Y: Multiple Absolute Stereocontrol in Cascade Lactone Formation via Dynamic Kinetic Resolution Driven by the Asymmetric Transfer Hydrogenation of Keto Acids with Oxo-Tethered Ruthenium Catalysts. J Am Chem Soc. 2019 Oct 16;141(41):16354-16361. doi: 10.1021/jacs.9b07297. Epub  2019 Sep 24. [PubMed:31502833  ] 
  5. Trapp T, Kirchner T, Birk F, Fraatz MA, Zorn H: Biosynthesis of Stereoisomers of Dill Ether and Wine Lactone by Pleurotus sapidus. J Agric Food Chem. 2019 Dec 11;67(49):13400-13411. doi: 10.1021/acs.jafc.8b07263.  Epub 2019 Mar 14. [PubMed:30813719  ] 
  6. Sellami I, Mall V, Schieberle P: Changes in the Key Odorants and Aroma Profiles of Hamlin and Valencia Orange Juices Not from Concentrate (NFC) during Chilled Storage. J Agric Food Chem. 2018 Jul 18;66(28):7428-7440. doi: 10.1021/acs.jafc.8b02257.  Epub 2018 Jul 3. [PubMed:29889522  ] 
  7. Kreissl J, Schieberle P: Characterization of Aroma-Active Compounds in Italian Tomatoes with Emphasis on New Odorants. J Agric Food Chem. 2017 Jun 28;65(25):5198-5208. doi: 10.1021/acs.jafc.7b01108.  Epub 2017 Jun 14. [PubMed:28573856  ] 
  8. Kroener EM, Buettner A: Unravelling important odorants in horseradish (Armoracia rusticana). Food Chem. 2017 Oct 1;232:455-465. doi: 10.1016/j.foodchem.2017.04.042. Epub 2017  Apr 7. [PubMed:28490098  ] 
  9. Ilc T, Halter D, Miesch L, Lauvoisard F, Kriegshauser L, Ilg A, Baltenweck R, Hugueney P, Werck-Reichhart D, Duchene E, Navrot N: A grapevine cytochrome P450 generates the precursor of wine lactone, a key odorant in wine. New Phytol. 2017 Jan;213(1):264-274. doi: 10.1111/nph.14139. Epub 2016 Aug 25. [PubMed:27560385  ]