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Showing metabocard for L-Aspartate-semialdehyde (HMDB0012249)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-04-06 16:21:44 UTC
Update Date2023-02-21 17:17:46 UTC
HMDB IDHMDB0012249
Secondary Accession Numbers
  • HMDB12249
Metabolite Identification
Common NameL-Aspartate-semialdehyde
DescriptionL-Aspartate-semialdehyde (CAS: 15106-57-7) is involved in both the lysine biosynthesis I and homoserine biosynthesis pathways. In the lysine biosynthesis I pathway, L-aspartate-semialdehyde is produced from a reaction between L-aspartyl-4-phosphate and NADPH, with phosphate and NADP+ as byproducts. The reaction is catalyzed by aspartate-semialdehyde dehydrogenase. L-Aspartate-semialdehyde reacts with pyruvate to produce L-2,3-dihydrodipicolinate and water. Dihydrodipicolinate synthase catalyzes this reaction. In the homoserine biosynthesis pathway, L-aspartate-semialdehyde is produced from a reaction between L-aspartyl-4-phosphate and NADPH, with phosphate and NADP+ as byproducts. The reaction is catalyzed by aspartate-semialdehyde dehydrogenase. L-Aspartate-semialdehyde reacts with NAD(P)H and H+ to form homoserine and NAD(P)+.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012249 (L-Aspartate-semialdehyde)

  Mrv1652309042000352D          

  8  7  0  0  0  0            999 V2000
   -2.9574    1.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6718    0.7254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9574    1.9629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2429    0.7254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2429   -0.0995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5284    1.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8139    0.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995    1.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  4  5  1  6  0  0  0
M  END
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3D MOL for HMDB0012249 (L-Aspartate-semialdehyde)

HMDB0012249
     RDKit          3D
L-Aspartate-semialdehyde
 15 14  0  0  0  0  0  0  0  0999 V2000
    1.0328    1.0216    1.0598 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2813   -0.1054    0.5280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0670    0.3470    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280   -0.7834   -0.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9231   -0.6482   -1.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1056   -0.7731   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634   -1.7894   -1.1497 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3585   -0.2610   -0.7886 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8983    1.8914    0.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8671    1.1291    2.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1076   -0.8200    1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9729    1.1605   -0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6117    0.7610    0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4368   -1.7886   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4248    0.6584   -1.2475 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
  2  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  1
  3 12  1  0
  3 13  1  0
  4 14  1  0
  8 15  1  0
M  END
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3D SDF for HMDB0012249 (L-Aspartate-semialdehyde)

  Mrv1652309042000352D          

  8  7  0  0  0  0            999 V2000
   -2.9574    1.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6718    0.7254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9574    1.9629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2429    0.7254    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2429   -0.0995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5284    1.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8139    0.7254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0995    1.1379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  1  3  2  0  0  0  0
  2  1  1  0  0  0  0
  4  5  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0012249

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO3/c5-3(1-2-6)4(7)8/h2-3H,1,5H2,(H,7,8)/t3-/m0/s1

> <INCHI_KEY>
HOSWPDPVFBCLSY-VKHMYHEASA-N

> <FORMULA>
C4H7NO3

> <MOLECULAR_WEIGHT>
117.1033

> <EXACT_MASS>
117.042593095

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.50910247684092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-oxobutanoic acid

> <ALOGPS_LOGP>
-2.73

> <JCHEM_LOGP>
-3.641399029317828

> <ALOGPS_LOGS>
0.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.542861157242697

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.950886233397024

> <JCHEM_PKA_STRONGEST_BASIC>
8.984374351722682

> <JCHEM_POLAR_SURFACE_AREA>
80.39000000000001

> <JCHEM_REFRACTIVITY>
25.607300000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.25e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
L-aspartic 4-semialdehyde

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0012249 (L-Aspartate-semialdehyde)

HMDB0012249
     RDKit          3D
L-Aspartate-semialdehyde
 15 14  0  0  0  0  0  0  0  0999 V2000
    1.0328    1.0216    1.0598 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2813   -0.1054    0.5280 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0670    0.3470    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8280   -0.7834   -0.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9231   -0.6482   -1.0316 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1056   -0.7731   -0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634   -1.7894   -1.1497 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3585   -0.2610   -0.7886 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8983    1.8914    0.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8671    1.1291    2.0840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1076   -0.8200    1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9729    1.1605   -0.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6117    0.7610    0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4368   -1.7886   -0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4248    0.6584   -1.2475 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
  2  6  1  0
  6  7  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  1
  3 12  1  0
  3 13  1  0
  4 14  1  0
  8 15  1  0
M  END
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PDB for HMDB0012249 (L-Aspartate-semialdehyde)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -5.520   2.124   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.854   1.354   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      -5.520   3.664   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.187   1.354   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -4.187  -0.186   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.853   2.124   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.519   1.354   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.186   2.124   0.000  0.00  0.00           O+0
CONECT    1    4    3    2                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    6    5                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for HMDB0012249 (L-Aspartate-semialdehyde)

COMPND    HMDB0012249
HETATM    1  N1  UNL     1       1.033   1.022   1.060  1.00  0.00           N  
HETATM    2  C1  UNL     1       0.281  -0.105   0.528  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.067   0.347   0.010  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.828  -0.783  -0.516  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.923  -0.648  -1.032  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.106  -0.773  -0.499  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.763  -1.789  -1.150  1.00  0.00           O  
HETATM    8  O3  UNL     1       2.358  -0.261  -0.789  1.00  0.00           O  
HETATM    9  H1  UNL     1       0.898   1.891   0.528  1.00  0.00           H  
HETATM   10  H2  UNL     1       0.867   1.129   2.084  1.00  0.00           H  
HETATM   11  H3  UNL     1       0.108  -0.820   1.336  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.973   1.161  -0.745  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.612   0.761   0.892  1.00  0.00           H  
HETATM   14  H6  UNL     1      -1.437  -1.789  -0.461  1.00  0.00           H  
HETATM   15  H7  UNL     1       2.425   0.658  -1.247  1.00  0.00           H  
CONECT    1    2    9   10
CONECT    2    3    6   11
CONECT    3    4   12   13
CONECT    4    5    5   14
CONECT    6    7    7    8
CONECT    8   15
END
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SMILES for HMDB0012249 (L-Aspartate-semialdehyde)

N[C@@H](CC=O)C(O)=O
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INCHI for HMDB0012249 (L-Aspartate-semialdehyde)

InChI=1S/C4H7NO3/c5-3(1-2-6)4(7)8/h2-3H,1,5H2,(H,7,8)/t3-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC4H7NO3
Average Molecular Weight117.1033
Monoisotopic Molecular Weight117.042593095
IUPAC Name(2S)-2-amino-4-oxobutanoic acid
Traditional NameL-aspartic 4-semialdehyde
CAS Registry Number2338-03-6
SMILES
N[C@@H](CC=O)C(O)=O
InChI Identifier
InChI=1S/C4H7NO3/c5-3(1-2-6)4(7)8/h2-3H,1,5H2,(H,7,8)/t3-/m0/s1
InChI KeyHOSWPDPVFBCLSY-VKHMYHEASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Alpha-hydrogen aldehyde
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Aldehyde
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Primary aliphatic amine
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Route of exposureSource
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 LocationsNot Available
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 IDFDB028891
KNApSAcK IDC00007469
Chemspider ID388372
KEGG Compound IDC00441
BioCyc IDL-ASPARTATE-SEMIALDEHYDE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439235
PDB IDNot Available
ChEBI ID18051
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available