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Showing NP-Card for Isomintlactone (NP0048446)

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Record Information
Version2.0
Created at2022-03-17 20:56:36 UTC
Updated at2022-03-17 20:56:36 UTC
NP-MRD IDNP0048446
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsomintlactone
DescriptionIsomintlactone, also known as menthalactone, belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Isomintlactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Isomintlactone is found, on average, in the highest concentration within peppermints. Isomintlactone has also been detected, but not quantified in, herbs and spices. This could make isomintlactone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048446 (Isomintlactone)


  Mrv0541 02241217072D          

 12 13  0  0  0  0            999 V2000
    1.5668    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7418    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2468    1.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946    0.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5668   -1.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9897   -1.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1646   -1.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946   -0.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946   -0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547   -0.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946    1.8964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  2  0  0  0  0
  3  4  1  0  0  0  0
  3 12  2  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  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
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3D MOL for NP0048446 (Isomintlactone)

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3D SDF for NP0048446 (Isomintlactone)

  Mrv0541 02241217072D          

 12 13  0  0  0  0            999 V2000
    1.5668    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7418    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2468    1.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946    0.8243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5668   -1.8964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9897   -1.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1646   -1.5664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946   -0.9893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3297   -0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946   -0.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547   -0.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946    1.8964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  2  0  0  0  0
  3  4  1  0  0  0  0
  3 12  2  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  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>
NP0048446

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2=C(C)C(=O)OC2C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h6,9H,3-5H2,1-2H3

> <INCHI_KEY>
VUVQBYIJRDUVHT-UHFFFAOYSA-N

> <FORMULA>
C10H14O2

> <MOLECULAR_WEIGHT>
166.217

> <EXACT_MASS>
166.099379692

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.454261380943557

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.382486628

> <ALOGPS_LOGS>
-1.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.3174497753173

> <JCHEM_PKA_STRONGEST_BASIC>
-6.88372860506763

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
46.176700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6-dimethyl-5,6,7,7a-tetrahydro-4H-1-benzofuran-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048446 (Isomintlactone)
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PDB for NP0048446 (Isomintlactone)
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  C   UNK     0       2.925   0.769   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.385   0.769   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.461   2.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.923   1.539   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.925  -3.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.847  -2.463   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.307  -2.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.923  -1.847   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.615  -0.461   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.923  -0.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.155  -0.923   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.923   3.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3   10                                                       
CONECT    5    6                                                            
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    2    8   10                                                  
CONECT   10    4    9   11                                                  
CONECT   11    6   10                                                       
CONECT   12    3                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0048446 (Isomintlactone)
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SMILES for NP0048446 (Isomintlactone)
CC1CCC2=C(C)C(=O)OC2C1
Download
INCHI for NP0048446 (Isomintlactone)
InChI=1S/C10H14O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h6,9H,3-5H2,1-2H3
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View in JSmol
Synonyms
ValueSource
(+)-IsomintlactoneHMDB
5,6,7,7a-Tetrahydro-3,6-dimethyl-(4H)-benzofuran-2-oneHMDB
5,6,7,7a-Tetrahydro-3,6-dimethyl-2(4H)-benzofuranoneHMDB
MenthalactoneHMDB
MintlactoneHMDB
IsomintlactoneMeSH
Chemical FormulaC10H14O2
Average Mass166.2170 Da
Monoisotopic Mass166.09938 Da
IUPAC Name3,6-dimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one
Traditional Name3,6-dimethyl-5,6,7,7a-tetrahydro-4H-1-benzofuran-2-one
CAS Registry Number75684-66-1
SMILES
CC1CCC2=C(C)C(=O)OC2C1
InChI Identifier
InChI=1S/C10H14O2/c1-6-3-4-8-7(2)10(11)12-9(8)5-6/h6,9H,3-5H2,1-2H3
InChI KeyVUVQBYIJRDUVHT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Mentha x piperitaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzofurans  
Sub ClassNot Available
Direct ParentBenzofurans  
Alternative Parents
Substituents
  • Benzofuran
    • 

  • 2-furanone
    • 

  • Dihydrofuran
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP2.26ALOGPS
logP2.38ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)15.32ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.18 m³·mol⁻¹ChemAxon
Polarizability18.45 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036084  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014920  
KNApSAcK IDNot Available
Chemspider ID85151  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound94349  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available