Np mrd loader

Showing NP-Card for 5-Acetyl-3,4-dihydro-2H-pyrrole (NP0046142)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-03-17 19:49:10 UTC
Updated at2022-03-17 19:49:10 UTC
NP-MRD IDNP0046142
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Acetyl-3,4-dihydro-2H-pyrrole
Description5-Acetyl-3,4-dihydro-2H-pyrrole, also known as 2AP or APR, belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms. It is one of the key odourants of the crust of bread and considered to be responsible for the cracker-like odour properties. A pyrroline that is 1-pyrroline in which the hydrogen at position 2 is replaced by an acetyl group. 5-Acetyl-3,4-dihydro-2H-pyrrole is a strong basic compound (based on its pKa). 5-Acetyl-3,4-dihydro-2H-pyrrole is a sweet, ham, and nut tasting compound. Outside of the human body, 5-Acetyl-3,4-dihydro-2H-pyrrole has been detected, but not quantified in, cereals and cereal products and tortilla chips. This could make 5-acetyl-3,4-dihydro-2H-pyrrole a potential biomarker for the consumption of these foods. It is an aroma and flavour compound present in jasmine rice and basmati rice. It is responsible for the 'popcorn' aroma in a large variety of cereal and food products. 5-Acetyl-3,4-dihydro-2H-pyrrole is found in Pandanus amaryllifolius. 5-Acetyl-3,4-dihydro-2H-pyrrole was first documented in 2002 (PMID: 12428963). In bread, it is primarily generated during baking but amounts are influenced by ingredient composition and fermentation conditions (PMID: 12517110) (PMID: 16356012) (PMID: 16771451) (PMID: 20497370) (PMID: 20800726) (PMID: 22404867).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0046142 (5-Acetyl-3,4-dihydro-2H-pyrrole)


  Mrv0541 05061305522D          

  8  8  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  2  0  0  0  0
M  END
Download

3D MOL for NP0046142 (5-Acetyl-3,4-dihydro-2H-pyrrole)

Download
3D SDF for NP0046142 (5-Acetyl-3,4-dihydro-2H-pyrrole)

  Mrv0541 05061305522D          

  8  8  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  7  6  2  0  0  0  0
  8  5  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046142

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)C1=NCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3

> <INCHI_KEY>
DQBQWWSFRPLIAX-UHFFFAOYSA-N

> <FORMULA>
C6H9NO

> <MOLECULAR_WEIGHT>
111.1418

> <EXACT_MASS>
111.068413915

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
12.01402445253885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(3,4-dihydro-2H-pyrrol-5-yl)ethan-1-one

> <ALOGPS_LOGP>
0.19

> <JCHEM_LOGP>
0.8588400190000001

> <ALOGPS_LOGS>
-1.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.440199812800223

> <JCHEM_PKA_STRONGEST_BASIC>
3.7718036484536803

> <JCHEM_POLAR_SURFACE_AREA>
29.43

> <JCHEM_REFRACTIVITY>
31.389899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetyl-1-pyrroline

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0046142 (5-Acetyl-3,4-dihydro-2H-pyrrole)
Download
PDB for NP0046142 (5-Acetyl-3,4-dihydro-2H-pyrrole)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    7                                                       
CONECT    5    1    6    8                                                  
CONECT    6    3    5    7                                                  
CONECT    7    4    6                                                       
CONECT    8    5                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

Download
3D PDB for NP0046142 (5-Acetyl-3,4-dihydro-2H-pyrrole)
Download
SMILES for NP0046142 (5-Acetyl-3,4-dihydro-2H-pyrrole)
CC(=O)C1=NCCC1
Download
INCHI for NP0046142 (5-Acetyl-3,4-dihydro-2H-pyrrole)
InChI=1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3
Download
View in JSmol
Synonyms
ValueSource
2-Acetyl-4,5-dihydro-3H-pyrroleChEBI
2APChEBI
APRChEBI
1-(3,4-Dihydro-2H-pyrrol-5-yl)ethanoneHMDB
1-(3,4-Dihydro-2H-pyrrol-5-yl)ethanone, 9ciHMDB
1-Pyrroline, 2-acetylHMDB
2-Acetyl-1-pyrollineHMDB
2-Acetyl-1-pyrrolineHMDB
2-AcetylpyrrolineHMDB
Chemical FormulaC6H9NO
Average Mass111.1418 Da
Monoisotopic Mass111.06841 Da
IUPAC Name1-(3,4-dihydro-2H-pyrrol-5-yl)ethan-1-one
Traditional Name2-acetyl-1-pyrroline
CAS Registry Number85213-22-5
SMILES
CC(=O)C1=NCCC1
InChI Identifier
InChI=1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3
InChI KeyDQBQWWSFRPLIAX-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pandanus amaryllifoliusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrrolines  
Sub ClassNot Available
Direct ParentPyrrolines  
Alternative Parents
Substituents
  • Pyrroline
    • 

  • Ketimine
    • 

  • Ketone
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic 1,3-dipolar compound
    • 

  • Azacycle
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Imine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • 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
logP0.19ALOGPS
logP0.86ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)18.44ChemAxon
pKa (Strongest Basic)3.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.43 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity31.39 m³·mol⁻¹ChemAxon
Polarizability12.01 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031308  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003364  
KNApSAcK IDNot Available
Chemspider ID456071  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Acetyl-1-pyrroline  
METLIN IDNot Available
PubChem Compound522834  
PDB IDNot Available
ChEBI ID67125  
Good Scents IDNot Available
References
General References
  1. Costello PJ, Henschke PA: Mousy off-flavor of wine: precursors and biosynthesis of the causative N-heterocycles 2-ethyltetrahydropyridine, 2-acetyltetrahydropyridine, and 2-acetyl-1-pyrroline by Lactobacillus hilgardii DSM 20176. J Agric Food Chem. 2002 Nov 20;50(24):7079-87. doi: 10.1021/jf020341r. [PubMed:12428963  ] 
  2. Wongpornchai S, Sriseadka T, Choonvisase S: Identification and quantitation of the rice aroma compound, 2-acetyl-1-pyrroline, in bread flowers (Vallaris glabra Ktze). J Agric Food Chem. 2003 Jan 15;51(2):457-62. doi: 10.1021/jf025856x. [PubMed:12517110  ] 
  3. Harrison TJ, Dake GR: An expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1,2,3,4-tetrahydropyridine and 2-acetyl-1-pyrroline. J Org Chem. 2005 Dec 23;70(26):10872-4. doi: 10.1021/jo051940a. [PubMed:16356012  ] 
  4. Adams A, De Kimpe N: Chemistry of 2-acetyl-1-pyrroline, 6-acetyl-1,2,3,4-tetrahydropyridine, 2-acetyl-2-thiazoline, and 5-acetyl-2,3-dihydro-4H-thiazine: extraordinary Maillard flavor compounds. Chem Rev. 2006 Jun;106(6):2299-319. doi: 10.1021/cr040097y. [PubMed:16771451  ] 
  5. Arikit S, Yoshihashi T, Wanchana S, Uyen TT, Huong NT, Wongpornchai S, Vanavichit A: Deficiency in the amino aldehyde dehydrogenase encoded by GmAMADH2, the homologue of rice Os2AP, enhances 2-acetyl-1-pyrroline biosynthesis in soybeans (Glycine max L.). Plant Biotechnol J. 2011 Jan;9(1):75-87. doi: 10.1111/j.1467-7652.2010.00533.x. [PubMed:20497370  ] 
  6. Maraval I, Sen K, Agrebi A, Menut C, Morere A, Boulanger R, Gay F, Mestres C, Gunata Z: Quantification of 2-acetyl-1-pyrroline in rice by stable isotope dilution assay through headspace solid-phase microextraction coupled to gas chromatography-tandem mass spectrometry. Anal Chim Acta. 2010 Aug 24;675(2):148-55. doi: 10.1016/j.aca.2010.07.024. Epub 2010 Jul 21. [PubMed:20800726  ] 
  7. Poonlaphdecha J, Maraval I, Roques S, Audebert A, Boulanger R, Bry X, Gunata Z: Effect of timing and duration of salt treatment during growth of a fragrant rice variety on yield and 2-acetyl-1-pyrroline, proline, and GABA Levels. J Agric Food Chem. 2012 Apr 18;60(15):3824-30. doi: 10.1021/jf205130y. Epub 2012  Apr 5. [PubMed:22404867  ]