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Showing metabocard for 3-Aminopropionaldehyde (HMDB0001106)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:26 UTC
HMDB IDHMDB0001106
Secondary Accession Numbers
  • HMDB01106
Metabolite Identification
Common Name3-Aminopropionaldehyde
Description3-Aminopropionaldehyde, also known as 3-aminopropanal, 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. 3-Aminopropionaldehyde is a very strong basic compound (based on its pKa). 3-Aminopropionaldehyde exists in all living species, ranging from bacteria to humans. Within humans, 3-aminopropionaldehyde participates in a number of enzymatic reactions. In particular, 3-aminopropionaldehyde can be converted into β-alanine through its interaction with the enzyme aldehyde dehydrogenase, mitochondrial. In addition, 3-aminopropionaldehyde can be biosynthesized from 1,3-diaminopropane through its interaction with the enzyme membrane primary amine oxidase. In humans, 3-aminopropionaldehyde is involved in beta-alanine metabolism. Outside of the human body, 3-Aminopropionaldehyde has been detected, but not quantified in, several different foods, such as hard wheats, abalones, jackfruits, blackcurrants, and strawberries. This could make 3-aminopropionaldehyde a potential biomarker for the consumption of these foods. 3-Aminopropionaldehyde is a reactive aldehyde that mediates progressive neuronal necrosis and glial apoptosis.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001106 (3-Aminopropionaldehyde)

  Mrv0541 02231218552D          

  5  4  0  0  0  0            999 V2000
    0.0000    0.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154   -0.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154   -0.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345    0.1636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4345    0.1636    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  2  0  0  0  0
M  END
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3D MOL for HMDB0001106 (3-Aminopropionaldehyde)

HMDB0001106
     RDKit          3D
3-Aminopropionaldehyde
 12 11  0  0  0  0  0  0  0  0999 V2000
   -1.8631   -0.0636    0.5999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4968    0.3754    0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4117   -0.4240   -0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8198    0.0417   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5309   -0.1922    0.8043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5364    0.7179    0.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261   -0.8817   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2006    0.2382    1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3940    1.4346    0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -1.4866    0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0384   -0.3770   -1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2819    0.6173   -0.9652 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  2  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  2  9  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
M  END
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3D SDF for HMDB0001106 (3-Aminopropionaldehyde)

  Mrv0541 02231218552D          

  5  4  0  0  0  0            999 V2000
    0.0000    0.1636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7154   -0.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7154   -0.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4345    0.1636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4345    0.1636    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  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001106

> <DATABASE_NAME>
hmdb

> <SMILES>
NCCC=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H7NO/c4-2-1-3-5/h3H,1-2,4H2

> <INCHI_KEY>
PCXDJQZLDDHMGX-UHFFFAOYSA-N

> <FORMULA>
C3H7NO

> <MOLECULAR_WEIGHT>
73.0938

> <EXACT_MASS>
73.052763851

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
7.711784373202365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-aminopropanal

> <ALOGPS_LOGP>
-1.23

> <JCHEM_LOGP>
-1.069079073

> <ALOGPS_LOGS>
0.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.186910038653014

> <JCHEM_PKA_STRONGEST_BASIC>
9.675566866157903

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
19.777400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.44e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-aminopropanal

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0001106 (3-Aminopropionaldehyde)

HMDB0001106
     RDKit          3D
3-Aminopropionaldehyde
 12 11  0  0  0  0  0  0  0  0999 V2000
   -1.8631   -0.0636    0.5999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4968    0.3754    0.6886 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4117   -0.4240   -0.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8198    0.0417   -0.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5309   -0.1922    0.8043 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5364    0.7179    0.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261   -0.8817   -0.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2006    0.2382    1.7444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3940    1.4346    0.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4344   -1.4866    0.1283 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0384   -0.3770   -1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2819    0.6173   -0.9652 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  2  0
  1  6  1  0
  1  7  1  0
  2  8  1  0
  2  9  1  0
  3 10  1  0
  3 11  1  0
  4 12  1  0
M  END
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PDB for HMDB0001106 (3-Aminopropionaldehyde)

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       0.000   0.305   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.335  -0.462   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.335  -0.462   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -2.678   0.305   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0       2.678   0.305   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2                                                            
CONECT    5    3                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0001106 (3-Aminopropionaldehyde)

COMPND    HMDB0001106
HETATM    1  N1  UNL     1      -1.863  -0.064   0.600  1.00  0.00           N  
HETATM    2  C1  UNL     1      -0.497   0.375   0.689  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.412  -0.424  -0.248  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.820   0.042  -0.161  1.00  0.00           C  
HETATM    5  O1  UNL     1       2.531  -0.192   0.804  1.00  0.00           O  
HETATM    6  H1  UNL     1      -2.536   0.718   0.440  1.00  0.00           H  
HETATM    7  H2  UNL     1      -2.026  -0.882  -0.015  1.00  0.00           H  
HETATM    8  H3  UNL     1      -0.201   0.238   1.744  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.394   1.435   0.382  1.00  0.00           H  
HETATM   10  H5  UNL     1       0.434  -1.487   0.128  1.00  0.00           H  
HETATM   11  H6  UNL     1       0.038  -0.377  -1.292  1.00  0.00           H  
HETATM   12  H7  UNL     1       2.282   0.617  -0.965  1.00  0.00           H  
CONECT    1    2    6    7
CONECT    2    3    8    9
CONECT    3    4   10   11
CONECT    4    5    5   12
END
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SMILES for HMDB0001106 (3-Aminopropionaldehyde)

NCCC=O
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INCHI for HMDB0001106 (3-Aminopropionaldehyde)

InChI=1S/C3H7NO/c4-2-1-3-5/h3H,1-2,4H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
beta-Aminopropion aldehydeChEBI
b-Aminopropion aldehydeGenerator
Β-aminopropion aldehydeGenerator
3-AminopropanalHMDB
Chemical FormulaC3H7NO
Average Molecular Weight73.0938
Monoisotopic Molecular Weight73.052763851
IUPAC Name3-aminopropanal
Traditional Name3-aminopropanal
CAS Registry Number352-92-1
SMILES
NCCC=O
InChI Identifier
InChI=1S/C3H7NO/c4-2-1-3-5/h3H,1-2,4H2
InChI KeyPCXDJQZLDDHMGX-UHFFFAOYSA-N
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
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
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 IDFDB030407
KNApSAcK IDNot Available
Chemspider ID74
KEGG Compound IDC05665
BioCyc IDCPD-6082
BiGG ID46232
Wikipedia LinkNot Available
METLIN ID6007
PubChem Compound75
PDB IDNot Available
ChEBI ID18090
Food Biomarker OntologyNot Available
VMH IDBAMPPALD
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceBott, Kaspar. Amidomethylation of trichloroethylene and acetylene: syntheses of N-protected a-chloro-b-alanines and b-aminopropanals. Journal of the Chemical Society [Section] D: Chemical Communications (1969), (22), 1304.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ivanova S, Batliwalla F, Mocco J, Kiss S, Huang J, Mack W, Coon A, Eaton JW, Al-Abed Y, Gregersen PK, Shohami E, Connolly ES Jr, Tracey KJ: Neuroprotection in cerebral ischemia by neutralization of 3-aminopropanal. Proc Natl Acad Sci U S A. 2002 Apr 16;99(8):5579-84. Epub 2002 Apr 9. [PubMed:11943872 ]
  2. Yu Z, Li W, Hillman J, Brunk UT: Human neuroblastoma (SH-SY5Y) cells are highly sensitive to the lysosomotropic aldehyde 3-aminopropanal. Brain Res. 2004 Aug 6;1016(2):163-9. [PubMed:15246852 ]

Only showing the first 10 proteins. There are 14 proteins in total.

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Enzymes

Enzyme Details
1. Carbonyl reductase [NADPH] 1
General function:
Involved in oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73
Reactions
3-Aminopropionaldehyde → 3-aminopropan-1-oldetails
Enzyme Details
2. 4-trimethylaminobutyraldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
Enzyme Details
3. Aldehyde dehydrogenase, dimeric NADP-preferring
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular weight:
50394.57
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
Enzyme Details
4. Alpha-aminoadipic semialdehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
Enzyme Details
5. Aldehyde dehydrogenase family 1 member A3
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
Enzyme Details
6. Aldehyde dehydrogenase, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
Enzyme Details
7. Fatty aldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
Enzyme Details
8. Aldehyde dehydrogenase X, mitochondrial
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
3-Aminopropionaldehyde + NAD + Water → beta-Alanine + NADH + Hydrogen Iondetails
Enzyme Details
9. Amiloride-sensitive amine oxidase [copper-containing]
General function:
Involved in copper ion binding
Specific function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
ABP1
Uniprot ID:
P19801
Molecular weight:
85377.1
Enzyme Details
10. Membrane primary amine oxidase
General function:
Involved in copper ion binding
Specific function:
Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:
AOC3
Uniprot ID:
Q16853
Molecular weight:
84621.27
Reactions
1,3-Diaminopropane + Oxygen + Water → 3-Aminopropionaldehyde + Ammonia + Hydrogen peroxidedetails

Only showing the first 10 proteins. There are 14 proteins in total.

Show all enzymes and transporters