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Showing metabocard for 5-Acetyl-3,4-dihydro-2H-pyrrole (HMDB0031308)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:42:14 UTC
Update Date2023-02-21 17:20:19 UTC
HMDB IDHMDB0031308
Secondary Accession Numbers
  • HMDB31308
Metabolite 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. 5-Acetyl-3,4-dihydro-2H-pyrrole is a sweet, ham, and nut tasting compound. 5-Acetyl-3,4-dihydro-2H-pyrrole has been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, corns (Zea mays), taco, and tortilla chip. This could make 5-acetyl-3,4-dihydro-2H-pyrrole a potential biomarker for the consumption of these foods. 5-Acetyl-3,4-dihydro-2H-pyrrole is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 5-Acetyl-3,4-dihydro-2H-pyrrole.
Structure
Data?1677000019
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031308 (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
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3D MOL for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

HMDB0031308
     RDKit          3D
5-Acetyl-3,4-dihydro-2H-pyrrole
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.7640   -0.4571    0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6922    0.4998   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0428    1.6340   -0.5529 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2751    0.1819   -0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1672   -0.9421    0.3403 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -1.0523    0.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0912    0.2622   -0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8614    1.0566   -0.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8501   -1.2432   -0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -0.9695    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7096    0.0517    0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9001   -1.2952    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9164   -1.9043   -0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7247    0.1162   -1.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565    0.6989    0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8716    1.9966    0.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8624    1.3657   -1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  6 12  1  0
  6 13  1  0
  7 14  1  0
  7 15  1  0
  8 16  1  0
  8 17  1  0
M  END
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3D SDF for HMDB0031308 (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>
HMDB0031308

> <DATABASE_NAME>
hmdb

> <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 HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

HMDB0031308
     RDKit          3D
5-Acetyl-3,4-dihydro-2H-pyrrole
 17 17  0  0  0  0  0  0  0  0999 V2000
    2.7640   -0.4571    0.2190 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6922    0.4998   -0.1480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0428    1.6340   -0.5529 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2751    0.1819   -0.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1672   -0.9421    0.3403 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -1.0523    0.3539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0912    0.2622   -0.1324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8614    1.0566   -0.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8501   -1.2432   -0.5857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -0.9695    1.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7096    0.0517    0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9001   -1.2952    1.3950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9164   -1.9043   -0.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7247    0.1162   -1.0520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7565    0.6989    0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8716    1.9966    0.1968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8624    1.3657   -1.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  6 12  1  0
  6 13  1  0
  7 14  1  0
  7 15  1  0
  8 16  1  0
  8 17  1  0
M  END
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PDB for HMDB0031308 (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
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3D PDB for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

COMPND    HMDB0031308
HETATM    1  C1  UNL     1       2.764  -0.457   0.219  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.692   0.500  -0.148  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.043   1.634  -0.553  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.275   0.182  -0.059  1.00  0.00           C  
HETATM    5  N1  UNL     1      -0.167  -0.942   0.340  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.587  -1.052   0.354  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.091   0.262  -0.132  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.861   1.057  -0.398  1.00  0.00           C  
HETATM    9  H1  UNL     1       2.850  -1.243  -0.586  1.00  0.00           H  
HETATM   10  H2  UNL     1       2.404  -0.970   1.157  1.00  0.00           H  
HETATM   11  H3  UNL     1       3.710   0.052   0.393  1.00  0.00           H  
HETATM   12  H4  UNL     1      -1.900  -1.295   1.395  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.916  -1.904  -0.306  1.00  0.00           H  
HETATM   14  H6  UNL     1      -2.725   0.116  -1.052  1.00  0.00           H  
HETATM   15  H7  UNL     1      -2.757   0.699   0.641  1.00  0.00           H  
HETATM   16  H8  UNL     1      -0.872   1.997   0.197  1.00  0.00           H  
HETATM   17  H9  UNL     1      -0.862   1.366  -1.462  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    4
CONECT    4    5    5    8
CONECT    5    6
CONECT    6    7   12   13
CONECT    7    8   14   15
CONECT    8   16   17
END
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SMILES for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

CC(=O)C1=NCCC1
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INCHI for HMDB0031308 (5-Acetyl-3,4-dihydro-2H-pyrrole)

InChI=1S/C6H9NO/c1-5(8)6-3-2-4-7-6/h2-4H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
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, MeSH
2-AcetylpyrrolineMeSH, HMDB
Chemical FormulaC6H9NO
Average Molecular Weight111.1418
Monoisotopic Molecular Weight111.068413915
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
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
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point19.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point182.00 to 183.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility4103 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.019 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1583501
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .