Showing metabocard for N-Acetyl-D-valine (MMDBc0033170)

Microbial
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-11-19 04:37:34 UTC
Update Date2025-10-07 16:07:57 UTC
Metabolite IDMMDBc0033170
Metabolite Identification
Common NameN-Acetyl-D-valine
DescriptionN-Acetyl-D-valine is a member of the amino acid derivative chemical class, specifically an N-acetylated form of the branched-chain amino acid D-valine. Its chemical structure features an acetyl group attached to the nitrogen atom of the valine side chain, which alters its solubility and reactivity compared to the parent amino acid. In metabolic pathways, N-acetyl-D-valine is involved in various processes, including its synthesis via metabolic engineering techniques in microorganisms such as Escherichia coli, where it has been produced alongside other N-acetylated amino acids with notable efficiency (PMID:37689258 ). Additionally, N-acetyl-D-valine has been characterized for its kinetic properties, including Michaelis constants (K_m) and maximum reaction velocities (V_max), indicating its role as a substrate in enzymatic reactions (PMID:29509381 ). These studies highlight the compound's relevance in both synthetic biology applications and enzymatic studies, showcasing its potential utility in biotechnological contexts.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x0000561537c21c10>

76475
  Mrv0541 02241222392D          

 11 10  0  0  1  0            999 V2000
    2.0930    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8075   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3 10  2  0  0  0  0
  6  4  1  6  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000561537c21c10>

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3D SDF for #<Metabolite:0x0000561537c21c10>
76475
  Mrv0541 02241222392D          

 11 10  0  0  1  0            999 V2000
    2.0930    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8075   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  2  9  2  0  0  0  0
  3 10  2  0  0  0  0
  6  4  1  6  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033170

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H13NO3/c1-4(2)6(7(10)11)8-5(3)9/h4,6H,1-3H3,(H,8,9)(H,10,11)/t6-/m1/s1

> <INCHI_KEY>
IHYJTAOFMMMOPX-ZCFIWIBFSA-N

> <FORMULA>
C7H13NO3

> <MOLECULAR_WEIGHT>
159.183

> <EXACT_MASS>
159.089543287

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
16.21941714971011

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-acetamido-3-methylbutanoic acid

> <ALOGPS_LOGP>
0.29

> <JCHEM_LOGP>
0.12763050966666675

> <ALOGPS_LOGS>
-0.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.493791320219728

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.1129656275147015

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8747609507090192

> <JCHEM_POLAR_SURFACE_AREA>
66.39999999999999

> <JCHEM_REFRACTIVITY>
38.936699999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.56e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
D-valine, N-acetyl-

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x0000561537c21c10>
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PDB for #<Metabolite:0x0000561537c21c10>
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 76475                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       3.907   0.000   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.241   2.310   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.242  -1.540   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.908   0.770   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       6.574  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.574   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.241  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.908  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.241   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.242   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.576   0.770   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    6   10                                                       
CONECT    5    6    7    8                                                  
CONECT    6    4    5    9                                                  
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9    1    2    6                                                  
CONECT   10    3    4   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for #<Metabolite:0x0000561537c21c10>
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SMILES for #<Metabolite:0x0000561537c21c10>
CC(C)[C@@H](NC(C)=O)C(O)=O
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INCHI for #<Metabolite:0x0000561537c21c10>
InChI=1S/C7H13NO3/c1-4(2)6(7(10)11)8-5(3)9/h4,6H,1-3H3,(H,8,9)(H,10,11)/t6-/m1/s1
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SynonymsNot Available
Molecular FormulaC7H13NO3
Average Mass159.183
Monoisotopic Mass159.089543287
IUPAC Name(2R)-2-acetamido-3-methylbutanoic acid
Traditional NameD-valine, N-acetyl-
CAS Registry Number17916-88-0
SMILES
CC(C)[C@@H](NC(C)=O)C(O)=O
InChI Identifier
InChI=1S/C7H13NO3/c1-4(2)6(7(10)11)8-5(3)9/h4,6H,1-3H3,(H,8,9)(H,10,11)/t6-/m1/s1
InChI KeyIHYJTAOFMMMOPX-ZCFIWIBFSA-N