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Showing NP-Card for 4-Aminobutanal (NP0062931)

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Record Information
Version2.0
Created at2022-04-28 07:27:17 UTC
Updated at2022-04-28 07:27:18 UTC
NP-MRD IDNP0062931
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Aminobutanal
Description4-Aminobutyraldehyde, also known as 4-amino-butanal, belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group. 4-Aminobutyraldehyde is a very strong basic compound (based on its pKa). 4-Aminobutyraldehyde exists in all living species, ranging from bacteria to humans. Outside of the human body, 4-Aminobutyraldehyde has been detected, but not quantified in, several different foods, such as chinese bayberries, sour cherries, romaine lettuces, black salsifies, and green zucchinis. This could make 4-aminobutyraldehyde a potential biomarker for the consumption of these foods. 4-Aminobutanal is found in Escherichia coli and Santalum album . 4-Aminobutanal was first documented in 1987 (PMID: 3324802). An omega-aminoaldehyde that is butanal in which one of the hydrogens of the terminal methyl group has been replaced by an amino group (PMID: 8269919) (PMID: 8112751) (PMID: 1799975) (PMID: 8645224).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0062931 (4-Aminobutanal)


  Mrv0541 02231218552D          

  6  5  0  0  0  0            999 V2000
   -0.3562    0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562   -0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726    0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850    0.2046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7850   -0.2046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
M  END
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3D MOL for NP0062931 (4-Aminobutanal)

     RDKit          3D

 15 14  0  0  0  0  0  0  0  0999 V2000
    2.3335    0.2164    0.3028 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9097    0.2634    0.6261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1934   -0.5877   -0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2884   -0.6476   -0.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9770    0.6356   -0.2559 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1834    0.6546   -0.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4431    0.1277   -0.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8293    1.0072    0.7190 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8364   -0.1748    1.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6196    1.3215    0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5764   -1.6384   -0.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4665   -0.2974   -1.3860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -1.1604    0.7702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6921   -1.3023   -0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4952    1.5823   -0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
M  END
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3D SDF for NP0062931 (4-Aminobutanal)


  Mrv0541 02231218552D          

  6  5  0  0  0  0            999 V2000
   -0.3562    0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3562   -0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726   -0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726    0.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850    0.2046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7850   -0.2046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
  4  6  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0062931

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCCC=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H9NO/c5-3-1-2-4-6/h4H,1-3,5H2

> <INCHI_KEY>
DZQLQEYLEYWJIB-UHFFFAOYSA-N

> <FORMULA>
C4H9NO

> <MOLECULAR_WEIGHT>
87.1204

> <EXACT_MASS>
87.068413915

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
9.71572746213239

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-aminobutanal

> <ALOGPS_LOGP>
-0.73

> <JCHEM_LOGP>
-0.780417868

> <ALOGPS_LOGS>
0.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.828866437700317

> <JCHEM_PKA_STRONGEST_BASIC>
9.792866479907637

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
24.532400000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.59e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ω-aminoaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0062931 (4-Aminobutanal)

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PDB for NP0062931 (4-Aminobutanal)
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      -0.665   0.382   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.665  -0.382   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.002  -0.382   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.002   0.382   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -3.332   0.382   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0       3.332  -0.382   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3                                                            
CONECT    6    4                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0062931 (4-Aminobutanal)
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SMILES for NP0062931 (4-Aminobutanal)
NCCCC=O
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INCHI for NP0062931 (4-Aminobutanal)
InChI=1S/C4H9NO/c5-3-1-2-4-6/h4H,1-3,5H2
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View in JSmol
Synonyms
ValueSource
4-Amino-butyraldehydeChEBI
4-Amino-butanalHMDB
4-AminobutanalHMDB
4-AmmoniobutanalHMDB
gamma-AminobutyraldehydeHMDB
4-AminobutyraldehydeChEBI
Chemical FormulaC4H9NO
Average Mass87.1204 Da
Monoisotopic Mass87.06841 Da
IUPAC Name4-aminobutanal
Traditional Nameω-aminoaldehyde
CAS Registry NumberNot Available
SMILES
NCCCC=O
InChI Identifier
InChI=1S/C4H9NO/c5-3-1-2-4-6/h4H,1-3,5H2
InChI KeyDZQLQEYLEYWJIB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Escherichia coliBacteria
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Santalum albumPlant
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha-hydrogen aldehydes. These are aldehydes with the general formula HC(H)(R)C(=O)H, where R is an organyl group.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAlpha-hydrogen aldehydes  
Alternative Parents
Substituents
  • Alpha-hydrogen aldehyde
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Amine
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP-0.73ALOGPS
logP-0.78ChemAxon
logS0.47ALOGPS
pKa (Strongest Acidic)14.83ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.53 m³·mol⁻¹ChemAxon
Polarizability9.72 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001080  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022412  
KNApSAcK IDC00019656  
Chemspider ID115  
KEGG Compound IDC02903  
BioCyc ID4-AMINO-BUTYRALDEHYDE  
BiGG ID35337  
Wikipedia LinkNot Available
METLIN ID3225  
PubChem Compound118  
PDB IDNot Available
ChEBI ID17769  
Good Scents IDNot Available
References
General References
  1. Kurys G, Shah PC, Kikonygo A, Reed D, Ambroziak W, Pietruszko R: Human aldehyde dehydrogenase. cDNA cloning and primary structure of the enzyme that catalyzes dehydrogenation of 4-aminobutyraldehyde. Eur J Biochem. 1993 Dec 1;218(2):311-20. doi: 10.1111/j.1432-1033.1993.tb18379.x. [PubMed:8269919  ] 
  2. McPherson JD, Wasmuth JJ, Kurys G, Pietruszko R: Human aldehyde dehydrogenase: chromosomal assignment of the gene for the isozyme that metabolizes gamma-aminobutyraldehyde. Hum Genet. 1994 Feb;93(2):211-2. doi: 10.1007/BF00210615. [PubMed:8112751  ] 
  3. Ambroziak W, Kurys G, Pietruszko R: Aldehyde dehydrogenase (EC 1.2.1.3): comparison of subcellular localization of the third isozyme that dehydrogenates gamma-aminobutyraldehyde in rat, guinea pig and human liver. Comp Biochem Physiol B. 1991;100(2):321-7. doi: 10.1016/0305-0491(91)90382-n. [PubMed:1799975  ] 
  4. Ambroziak W, Pietruszko R: Human aldehyde dehydrogenase: metabolism of putrescine and histamine. Alcohol Clin Exp Res. 1987 Dec;11(6):528-32. doi: 10.1111/j.1530-0277.1987.tb00167.x. [PubMed:3324802  ] 
  5. Kikonyogo A, Pietruszko R: Aldehyde dehydrogenase from adult human brain that dehydrogenates gamma-aminobutyraldehyde: purification, characterization, cloning and distribution. Biochem J. 1996 May 15;316 ( Pt 1):317-24. doi: 10.1042/bj3160317. [PubMed:8645224  ]