Showing metabocard for (3S)-3-hydroxy-L-aspartic acid (MMDBc0032932)

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Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:27:51 UTC
Update Date2022-08-31 21:48:44 UTC
Metabolite IDMMDBc0032932
Metabolite Identification
Common Name(3S)-3-hydroxy-L-aspartic acid
Description3-Hydroxyaspartate is not found in normal proteins, it is found in cinnamycin, a 19-amino acid peptide with anti-tumor and anti-microbial activities that is produced by Streptomyces strains. (3S)-3-Hydroxy-L-aspartic acid (threo-3-hydroxyaspartate) is converted to oxaloacetate and ammonia by a 3-hydroxyaspartate dehydratase (SRY1p) in yeast. The role of this enzyme in yeast would be detoxification of naturally occuring 3-hydroxyaspartate. [PMID: 12951240 ]
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fd59473ee40>

  Mrv0541 02241222082D          

 10  9  0  0  1  0            999 V2000
   16.7913  -15.1813    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5299  -15.5593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1057  -15.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7948  -14.3326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2685  -15.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5187  -16.4565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0987  -16.4071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3385  -15.2627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9750  -15.6260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2685  -14.3683    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
  1  4  1  1  0  0  0
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007fd59473ee40>

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3D SDF for #<Metabolite:0x00007fd59473ee40>
  Mrv0541 02241222082D          

 10  9  0  0  1  0            999 V2000
   16.7913  -15.1813    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.5299  -15.5593    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.1057  -15.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7948  -14.3326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2685  -15.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5187  -16.4565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0987  -16.4071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3385  -15.2627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9750  -15.6260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2685  -14.3683    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
  1  4  1  1  0  0  0
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032932

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO5/c5-1(3(7)8)2(6)4(9)10/h1-2,6H,5H2,(H,7,8)(H,9,10)/t1-,2-/m0/s1

> <INCHI_KEY>
YYLQUHNPNCGKJQ-LWMBPPNESA-N

> <FORMULA>
C4H7NO5

> <MOLECULAR_WEIGHT>
149.1021

> <EXACT_MASS>
149.032422339

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
12.101034813920721

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-2-amino-3-hydroxybutanedioic acid

> <ALOGPS_LOGP>
-3.43

> <JCHEM_LOGP>
-4.423453042360231

> <ALOGPS_LOGS>
-0.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.364745502137772

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.570691986541146

> <JCHEM_PKA_STRONGEST_BASIC>
9.076730403683923

> <JCHEM_POLAR_SURFACE_AREA>
120.85000000000002

> <JCHEM_REFRACTIVITY>
27.870900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxyaspartic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fd59473ee40>
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PDB for #<Metabolite:0x00007fd59473ee40>
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      31.344 -28.338   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.722 -29.044   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.064 -29.183   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      31.350 -26.754   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      34.101 -28.358   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      32.702 -30.719   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      30.051 -30.627   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      28.632 -28.490   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      35.420 -29.169   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      34.101 -26.821   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1                                                            
CONECT    5    2    9   10                                                  
CONECT    6    2                                                            
CONECT    7    3                                                            
CONECT    8    3                                                            
CONECT    9    5                                                            
CONECT   10    5                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

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3D PDB for #<Metabolite:0x00007fd59473ee40>
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SMILES for #<Metabolite:0x00007fd59473ee40>
N[C@@H]([C@H](O)C(O)=O)C(O)=O
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INCHI for #<Metabolite:0x00007fd59473ee40>
InChI=1S/C4H7NO5/c5-1(3(7)8)2(6)4(9)10/h1-2,6H,5H2,(H,7,8)(H,9,10)/t1-,2-/m0/s1
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Synonyms
Molecular FormulaC4H7NO5
Average Mass149.1021
Monoisotopic Mass149.032422339
IUPAC Name(2S,3S)-2-amino-3-hydroxybutanedioic acid
Traditional Name3-hydroxyaspartic acid
CAS Registry Number7298-99-9
SMILES
N[C@@H]([C@H](O)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H7NO5/c5-1(3(7)8)2(6)4(9)10/h1-2,6H,5H2,(H,7,8)(H,9,10)/t1-,2-/m0/s1
InChI KeyYYLQUHNPNCGKJQ-LWMBPPNESA-N