Np mrd loader

Showing NP-Card for Acetylglycine (NP0000716)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:17:44 UTC
NP-MRD IDNP0000716
Secondary Accession NumbersNone
Natural Product Identification
Common NameAcetylglycine
DescriptionN-acetylglycine is used is in biological research of peptidomimetics. It is used as the blocking agent of the N-terminus to prepare unnatural and unusual amino acids and amino acid analogs as well as to modify peptides. N-Substituted glycine analogs are widely used in peptidomimetics and drug research. Excessive amounts N-acetyl amino acids including N-acetylglycine (as well as N-acetylserine, N-acetylglutamine, N-acetylglutamate, N-acetylalanine, Nacetylmethionine and smaller amounts of N-acetylthreonine, N-acetylleucine, N-acetylvaline and N-acetylisoleucine) can be detected in the urine with individuals with acylase I defiency, a genetic disorder. This enzyme is involved in the degradation of N-acylated proteins. Individuals with this disorder will experience convulsions, hearing loss ond difficulty feeding.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000716 (Acetylglycine)


  Mrv1652305271900012D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    0.7146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9521    1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666    0.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3812    1.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
Download

3D MOL for NP0000716 (Acetylglycine)

HMDB0000532
     RDKit          3D
Acetylglycine
 15 14  0  0  0  0  0  0  0  0999 V2000
   -2.6713    0.3317    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2630    0.7184    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522    1.9057   -0.2606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2416   -0.2615    0.0985 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1186    0.1352   -0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0651   -0.9927   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6828   -2.1427    0.2247 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4021   -0.7618   -0.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    1.1270    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6936   -0.6224    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317    0.2118   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5003   -1.2524    0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756    0.4950   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4547    0.9671    0.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7980    0.1416   -0.5106 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  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  8 15  1  0
M  END
Download

3D SDF for NP0000716 (Acetylglycine)


  Mrv1652305271900012D          

  8  7  0  0  0  0            999 V2000
   -0.1914    0.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376    0.7146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9521    1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666    0.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3812    1.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000716

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H7NO3/c1-3(6)5-2-4(7)8/h2H2,1H3,(H,5,6)(H,7,8)

> <INCHI_KEY>
OKJIRPAQVSHGFK-UHFFFAOYSA-N

> <FORMULA>
C4H7NO3

> <MOLECULAR_WEIGHT>
117.1033

> <EXACT_MASS>
117.042593095

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.690091704986068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-acetamidoacetic acid

> <ALOGPS_LOGP>
-0.89

> <JCHEM_LOGP>
-1.3286289540000003

> <ALOGPS_LOGS>
-0.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.581933746898102

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.772480582340469

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0460057413187704

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
25.4472

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aceturate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000716 (Acetylglycine)

HMDB0000532
     RDKit          3D
Acetylglycine
 15 14  0  0  0  0  0  0  0  0999 V2000
   -2.6713    0.3317    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2630    0.7184    0.0355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9522    1.9057   -0.2606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2416   -0.2615    0.0985 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1186    0.1352   -0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0651   -0.9927   -0.0736 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6828   -2.1427    0.2247 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4021   -0.7618   -0.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1434    1.1270    0.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6936   -0.6224    0.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2317    0.2118   -0.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5003   -1.2524    0.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756    0.4950   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4547    0.9671    0.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7980    0.1416   -0.5106 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  2  0
  6  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  4 12  1  0
  5 13  1  0
  5 14  1  0
  8 15  1  0
M  END
Download

PDB for NP0000716 (Acetylglycine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       2.310   1.334   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.978   1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.312   2.104   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.978  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for NP0000716 (Acetylglycine)

COMPND    HMDB0000532
HETATM    1  C1  UNL     1      -2.671   0.332   0.317  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.263   0.718   0.036  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.952   1.906  -0.261  1.00  0.00           O  
HETATM    4  N1  UNL     1      -0.242  -0.261   0.099  1.00  0.00           N  
HETATM    5  C3  UNL     1       1.119   0.135  -0.179  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.065  -0.993  -0.074  1.00  0.00           C  
HETATM    7  O2  UNL     1       1.683  -2.143   0.225  1.00  0.00           O  
HETATM    8  O3  UNL     1       3.402  -0.762  -0.312  1.00  0.00           O  
HETATM    9  H1  UNL     1      -3.143   1.127   0.958  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.694  -0.622   0.885  1.00  0.00           H  
HETATM   11  H3  UNL     1      -3.232   0.212  -0.633  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.500  -1.252   0.346  1.00  0.00           H  
HETATM   13  H5  UNL     1       1.176   0.495  -1.244  1.00  0.00           H  
HETATM   14  H6  UNL     1       1.455   0.967   0.493  1.00  0.00           H  
HETATM   15  H7  UNL     1       3.798   0.142  -0.511  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    4
CONECT    4    5   12
CONECT    5    6   13   14
CONECT    6    7    7    8
CONECT    8   15
END
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SMILES for NP0000716 (Acetylglycine)

CC(=O)NCC(O)=O
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INCHI for NP0000716 (Acetylglycine)

InChI=1S/C4H7NO3/c1-3(6)5-2-4(7)8/h2H2,1H3,(H,5,6)(H,7,8)
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View in JSmol
Synonyms
ValueSource
Ac-gly-OHChEBI
Acetamidoacetic acidChEBI
Aceturic acidChEBI
Acetylamino-acetic acidChEBI
Acetylaminoacetic acidChEBI
Ethanoylaminoethanoic acidChEBI
AcetamidoacetateGenerator
AcetateGenerator
Acetic acidGenerator
Acetylamino-acetateGenerator
AcetylaminoacetateGenerator
EthanoylaminoethanoateGenerator
15N-Acetylglycine a-radicalHMDB
2-AcetamidoacetateHMDB
2-Acetamidoacetic acidHMDB
Ac glyHMDB
AceturateHMDB
AcetylglycocollHMDB
N-Acetyl-glycineHMDB
N-AcetylglycineHMDB
N-Acetylglycine sodium saltHMDB
AcetylglycinateHMDB
AcetylglycineChEBI
Chemical FormulaC4H7NO3
Average Mass117.1033 Da
Monoisotopic Mass117.04259 Da
IUPAC Name2-acetamidoacetic acid
Traditional Nameaceturate
CAS Registry Number543-24-8
SMILES
CC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C4H7NO3/c1-3(6)5-2-4(7)8/h2H2,1H3,(H,5,6)(H,7,8)
InChI KeyOKJIRPAQVSHGFK-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Serum)KNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point207 - 209 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility26.3 mg/mL at 15 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility51.3 g/LALOGPS
logP-0.89ALOGPS
logP-1.3ChemAxon
logS-0.36ALOGPS
pKa (Strongest Acidic)3.77ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.45 m³·mol⁻¹ChemAxon
Polarizability10.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000532
DrugBank IDDB02713
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022100
KNApSAcK IDC00052177
Chemspider ID10507
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAceturic acid
METLIN ID5517
PubChem Compound10972
PDB IDNot Available
ChEBI ID40410
Good Scents IDrw1265641
References
General References
  1. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  2. Graca G, Duarte IF, J Goodfellow B, Carreira IM, Couceiro AB, Domingues Mdo R, Spraul M, Tseng LH, Gil AM: Metabolite profiling of human amniotic fluid by hyphenated nuclear magnetic resonance spectroscopy. Anal Chem. 2008 Aug 1;80(15):6085-92. doi: 10.1021/ac800907f. Epub 2008 Jun 20. [PubMed:18564856 ]
  3. Harper MS, Shen ZA, Barnett JF Jr, Krsmanovic L, Dakoulas EW, Delaney B: Toxicology studies with N-acetylglycine. Food Chem Toxicol. 2010 May;48(5):1321-7. doi: 10.1016/j.fct.2010.02.031. Epub 2010 Feb 25. [PubMed:20188778 ]
  4. Manna SK, Patterson AD, Yang Q, Krausz KW, Idle JR, Fornace AJ, Gonzalez FJ: UPLC-MS-based urine metabolomics reveals indole-3-lactic acid and phenyllactic acid as conserved biomarkers for alcohol-induced liver disease in the Ppara-null mouse model. J Proteome Res. 2011 Sep 2;10(9):4120-33. doi: 10.1021/pr200310s. Epub 2011 Jul 28. [PubMed:21749142 ]
  5. Boeckx B, Maes G: Comparison of the conformational behavior of amino acids and N-acetylated amino acids: a theoretical and matrix-isolation FT-IR study of N-acetylglycine. J Phys Chem A. 2012 Mar 1;116(8):1956-65. doi: 10.1021/jp211382u. Epub 2012 Feb 21. [PubMed:22273063 ]