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Showing NP-Card for 2-Isopropyl-3-methoxypyrazine (NP0049618)

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Record Information
Version2.0
Created at2022-03-17 21:15:23 UTC
Updated at2022-03-17 21:15:24 UTC
NP-MRD IDNP0049618
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Isopropyl-3-methoxypyrazine
Description2-Isopropyl-3-methoxypyrazine, also known as 2-methoxy-3-isopropylpyrazine, belongs to the class of organic compounds known as methoxypyrazines. These are pyrazines containing a methoxyl group attached to the pyrazine ring. 2-Isopropyl-3-methoxypyrazine is an extremely weak basic (essentially neutral) compound (based on its pKa). 2-Isopropyl-3-methoxypyrazine is a beany, earthy, and pea tasting compound. Outside of the human body, 2-Isopropyl-3-methoxypyrazine has been detected, but not quantified in, several different foods, such as green bell peppers, fishes, peppers, orange bell peppers, and yellow bell peppers. This could make 2-isopropyl-3-methoxypyrazine a potential biomarker for the consumption of these foods. Isopropyl methoxy pyrazine (IPMP) is a methoxypyrazine, a class of chemical compounds that produce odors. Two methoxypyrazine compounds, 3-isobutyl-2-methoxypyrazine (IBMP) and 3-isopropyl-2-methoxypyrazine, are considered to be important determinants of green flavours in Sauvignon blanc wines. IPMP is also an important flavour compound in coffee and is responsible for causing an off-taste called "potato taste" in East African coffee. It can be detected by human taste at concentrations of as low as 2 nanograms per litre. The odor is rather undesirable and is produced by the Asian lady beetle or by the actinomycete Streptomyces sp. The insects Antestiopsis are also implicated in causing the taste. 2-Isopropyl-3-methoxypyrazine is found in Asclepias curassavica, Coffea arabica, Panax ginseng and Panax notoginseng. The odor of IPMP tends to be undesirable in the case of certain wines.Cabernet Sauvignon has high levels of methoxypyrazines.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049618 (2-Isopropyl-3-methoxypyrazine)


  Mrv0541 02231215422D          

 11 11  0  0  0  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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 N   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 N   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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
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3D MOL for NP0049618 (2-Isopropyl-3-methoxypyrazine)

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3D SDF for NP0049618 (2-Isopropyl-3-methoxypyrazine)

  Mrv0541 02231215422D          

 11 11  0  0  0  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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 N   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 N   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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049618

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=NC=CN=C1C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2O/c1-6(2)7-8(11-3)10-5-4-9-7/h4-6H,1-3H3

> <INCHI_KEY>
NTOPKICPEQUPPH-UHFFFAOYSA-N

> <FORMULA>
C8H12N2O

> <MOLECULAR_WEIGHT>
152.1937

> <EXACT_MASS>
152.094963016

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
16.409760942094714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methoxy-3-(propan-2-yl)pyrazine

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
1.3495795206666665

> <ALOGPS_LOGS>
-0.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.8790385602220102

> <JCHEM_POLAR_SURFACE_AREA>
35.010000000000005

> <JCHEM_REFRACTIVITY>
42.31379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.14e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxy-3-isopropylpyrazine

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049618 (2-Isopropyl-3-methoxypyrazine)
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PDB for NP0049618 (2-Isopropyl-3-methoxypyrazine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+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  N   UNK     0       0.000   1.540   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0049618 (2-Isopropyl-3-methoxypyrazine)
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SMILES for NP0049618 (2-Isopropyl-3-methoxypyrazine)
COC1=NC=CN=C1C(C)C
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INCHI for NP0049618 (2-Isopropyl-3-methoxypyrazine)
InChI=1S/C8H12N2O/c1-6(2)7-8(11-3)10-5-4-9-7/h4-6H,1-3H3
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Synonyms
ValueSource
3-Isopropyl-2-methoxypyrazineHMDB
2-Methoxy-3-isopropylpyrazineHMDB
2-Isopropyl-3-methoxypyrazineMeSH
Chemical FormulaC8H12N2O
Average Mass152.1937 Da
Monoisotopic Mass152.09496 Da
IUPAC Name2-methoxy-3-(propan-2-yl)pyrazine
Traditional Name2-methoxy-3-isopropylpyrazine
CAS Registry Number25773-40-4
SMILES
COC1=NC=CN=C1C(C)C
InChI Identifier
InChI=1S/C8H12N2O/c1-6(2)7-8(11-3)10-5-4-9-7/h4-6H,1-3H3
InChI KeyNTOPKICPEQUPPH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Asclepias curassavicaLOTUS Database
Capsicum annuumFooDB
Coffea arabicaLOTUS Database
Panax ginsengLOTUS Database
Panax notoginsengLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxypyrazines. These are pyrazines containing a methoxyl group attached to the pyrazine ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDiazines  
Sub ClassPyrazines  
Direct ParentMethoxypyrazines  
Alternative Parents
Substituents
  • Methoxypyrazine
    • 

  • Alkyl aryl ether
    • 

  • Heteroaromatic compound
    • 

  • Azacycle
    • 

  • Ether
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic 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
logP2.08ALOGPS
logP1.35ChemAxon
logS-0.39ALOGPS
pKa (Strongest Basic)0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.01 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.31 m³·mol⁻¹ChemAxon
Polarizability16.41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0040340  
DrugBank IDDB01760  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020065  
KNApSAcK IDNot Available
Chemspider ID30649  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsopropyl methoxy pyrazine  
METLIN IDNot Available
PubChem Compound33166  
PDB IDIPZ  
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available