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Showing NP-Card for O-Acetylhomoserine (NP0045364)

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Record Information
Version2.0
Created at2022-03-17 19:18:40 UTC
Updated at2022-03-17 19:18:40 UTC
NP-MRD IDNP0045364
Secondary Accession NumbersNone
Natural Product Identification
Common NameO-Acetylhomoserine
DescriptionAcetylhomoserine, also known as homoserine acetate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Acetylhomoserine is a very strong basic compound (based on its pKa). Acetylhomoserine exists in all eukaryotes, ranging from yeast to humans. Outside of the human body, Acetylhomoserine is found, on average, in the highest concentration within common pea. Acetylhomoserine has also been detected, but not quantified in, milk (cow) and pulses. This could make acetylhomoserine a potential biomarker for the consumption of these foods. O-Acetylhomoserine is found in Escherichia coli. An alpha-amino acid that is homoserine in which the alcoholic hydroxy group has been converted to the corresponding acetate.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0045364 (O-Acetylhomoserine)


  Mrv1652307171819242D          

 11 10  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  4  2  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  3  1  0  0  0  0
 11  4  1  0  0  0  0
M  END
Download

3D MOL for NP0045364 (O-Acetylhomoserine)

     RDKit          3D

 22 21  0  0  0  0  0  0  0  0999 V2000
   -4.1244    0.1898    0.5453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9023   -0.1923   -0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9927   -0.9212   -1.2028 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6573    0.2337    0.2081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4694   -0.1140   -0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7177    0.5238    0.2327 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9547    0.1142   -0.5435 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0459   -1.3126   -0.5300 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1658    0.7956   -0.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1689    2.0542   -0.0476 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3103    0.1543    0.3631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5822   -0.7479    0.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8658    0.6535   -0.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8599    0.8651    1.3987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3338   -1.2032   -0.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5698    0.2951   -1.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690    1.6130    0.2096 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7455    0.0904    1.2570 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776    0.4356   -1.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4561   -1.7679    0.2029 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7993   -1.7580   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5470   -0.0010    1.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 11  1  0
  9 10  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  6
  8 20  1  0
  8 21  1  0
 11 22  1  0
M  END
Download

3D SDF for NP0045364 (O-Acetylhomoserine)


  Mrv1652307171819242D          

 11 10  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  4  2  0  0  0  0
  9  6  2  0  0  0  0
 10  6  1  0  0  0  0
 11  3  1  0  0  0  0
 11  4  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045364

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCCC(N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO4/c1-4(8)11-3-2-5(7)6(9)10/h5H,2-3,7H2,1H3,(H,9,10)

> <INCHI_KEY>
FCXZBWSIAGGPCB-UHFFFAOYSA-N

> <FORMULA>
C6H11NO4

> <MOLECULAR_WEIGHT>
161.1558

> <EXACT_MASS>
161.068807845

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.543185352052863

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(acetyloxy)-2-aminobutanoic acid

> <ALOGPS_LOGP>
-2.87

> <JCHEM_LOGP>
-3.387033704166865

> <ALOGPS_LOGS>
-0.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.015703027729805

> <JCHEM_PKA_STRONGEST_BASIC>
9.458194751674373

> <JCHEM_POLAR_SURFACE_AREA>
89.62

> <JCHEM_REFRACTIVITY>
36.057900000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.39e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
O-acetylhomoserine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0045364 (O-Acetylhomoserine)

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PDB for NP0045364 (O-Acetylhomoserine)
HEADER    PROTEIN                                 17-JUL-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-18         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       4.001   2.310   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       6.668   0.770   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    3    5                                                       
CONECT    3    2   11                                                       
CONECT    4    1    8   11                                                  
CONECT    5    2    6    7                                                  
CONECT    6    5    9   10                                                  
CONECT    7    5                                                            
CONECT    8    4                                                            
CONECT    9    6                                                            
CONECT   10    6                                                            
CONECT   11    3    4                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0045364 (O-Acetylhomoserine)
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SMILES for NP0045364 (O-Acetylhomoserine)
CC(=O)OCCC(N)C(O)=O
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INCHI for NP0045364 (O-Acetylhomoserine)
InChI=1S/C6H11NO4/c1-4(8)11-3-2-5(7)6(9)10/h5H,2-3,7H2,1H3,(H,9,10)
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View in JSmol
Synonyms
ValueSource
4-Acetoxy-2-aminobutanoic acidHMDB
Homoserine acetateHMDB
O-Acetyl-L-homoserineHMDB
O-AcetylhomoserineHMDB
Chemical FormulaC6H11NO4
Average Mass161.1558 Da
Monoisotopic Mass161.06881 Da
IUPAC Name4-(acetyloxy)-2-aminobutanoic acid
Traditional NameO-acetylhomoserine
CAS Registry Number7540-67-2
SMILES
CC(=O)OCCC(N)C(O)=O
InChI Identifier
InChI=1S/C6H11NO4/c1-4(8)11-3-2-5(7)6(9)10/h5H,2-3,7H2,1H3,(H,9,10)
InChI KeyFCXZBWSIAGGPCB-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
Escherichia coliBacteria
Pisum sativumFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentAlpha amino acids  
Alternative Parents
Substituents
  • Alpha-amino acid
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Fatty acid
    • 

  • Carboxylic acid ester
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Organic nitrogen compound
    • 

  • Organic oxide
    • 

  • 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-2.9ALOGPS
logP-3.4ChemAxon
logS-0.28ALOGPS
pKa (Strongest Acidic)2.02ChemAxon
pKa (Strongest Basic)9.46ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.62 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity36.06 m³·mol⁻¹ChemAxon
Polarizability15.54 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029423  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000523  
KNApSAcK IDNot Available
Chemspider ID513  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound528  
PDB IDNot Available
ChEBI ID7671  
Good Scents IDNot Available
References
General References