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Showing NP-Card for (2r)-2-{[(2r)-2-amino-1-hydroxypropylidene]amino}propanoic acid (NP0150264)

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Record Information
Version2.0
Created at2022-09-02 06:18:25 UTC
Updated at2022-09-02 06:18:25 UTC
NP-MRD IDNP0150264
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2r)-2-{[(2r)-2-amino-1-hydroxypropylidene]amino}propanoic acid
DescriptionD-Alanyl-D-alanine, also known as D-ala-D-ala or ala-ala, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. D-Alanyl-D-alanine is a very strong basic compound (based on its pKa). D-Alanyl-D-alanine exists in all living organisms, ranging from bacteria to humans. (2r)-2-{[(2r)-2-amino-1-hydroxypropylidene]amino}propanoic acid is found in Homo sapiens, Oryza punctata and Trypanosoma brucei. (2r)-2-{[(2r)-2-amino-1-hydroxypropylidene]amino}propanoic acid was first documented in 1981 (PMID: 6118181). A dipeptide comprising D-alanine with a D-alanyl residue attached to the alpha-nitrogen (PMID: 6423541) (PMID: 16030213) (PMID: 17418637).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0150264 ((2r)-2-{[(2r)-2-amino-1-hydroxypropylidene]amino}propanoic acid)


  Mrv0541 02231219442D          

 11 10  0  0  1  0            999 V2000
   18.6616  -20.6679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3761  -21.9055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5195  -19.8429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8051  -21.0805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9485  -20.6679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0906  -20.6679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.2341  -21.0805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.0906  -19.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2341  -21.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3761  -21.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5195  -20.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 10  2  0  0  0  0
  3 11  2  0  0  0  0
  6  4  1  1  0  0  0
  4 11  1  0  0  0  0
  7  5  1  6  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
M  END
Download

3D MOL for NP0150264 ((2r)-2-{[(2r)-2-amino-1-hydroxypropylidene]amino}propanoic acid)

     RDKit          3D

 23 22  0  0  0  0  0  0  0  0999 V2000
    2.5611   -0.7927   -0.7368 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1475    0.2217    0.3058 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0553    1.3256    0.2949 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7465    0.6523    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5309    1.8849    0.0323 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3253   -0.2782    0.1331 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6944    0.1424   -0.0188 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5174   -0.1891    1.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3655   -0.5287   -1.1573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7710   -1.3620   -1.8805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6863   -0.2474   -1.4547 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437   -0.6407   -0.9315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0131   -0.6189   -1.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4466   -1.8226   -0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2223   -0.2869    1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0338    1.8996    1.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0324    1.0575    0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1121   -1.2900    0.2331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    1.2580   -0.1142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4378    0.4354    1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8177   -1.2582    1.1859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9936    0.0722    2.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9546    0.3659   -2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  4  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
  2 15  1  1
  3 16  1  0
  3 17  1  0
  6 18  1  0
  7 19  1  6
  8 20  1  0
  8 21  1  0
  8 22  1  0
 11 23  1  0
M  END
Download

3D SDF for NP0150264 ((2r)-2-{[(2r)-2-amino-1-hydroxypropylidene]amino}propanoic acid)


  Mrv0541 02231219442D          

 11 10  0  0  1  0            999 V2000
   18.6616  -20.6679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3761  -21.9055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5195  -19.8429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8051  -21.0805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9485  -20.6679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0906  -20.6679    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.2341  -21.0805    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.0906  -19.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2341  -21.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3761  -21.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5195  -20.6679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  1  0  0  0  0
  2 10  2  0  0  0  0
  3 11  2  0  0  0  0
  6  4  1  1  0  0  0
  4 11  1  0  0  0  0
  7  5  1  6  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  7 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150264

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H12N2O3/c1-3(7)5(9)8-4(2)6(10)11/h3-4H,7H2,1-2H3,(H,8,9)(H,10,11)/t3-,4-/m1/s1

> <INCHI_KEY>
DEFJQIDDEAULHB-QWWZWVQMSA-N

> <FORMULA>
C6H12N2O3

> <MOLECULAR_WEIGHT>
160.1711

> <EXACT_MASS>
160.08479226

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
15.661226134276223

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(2R)-2-aminopropanamido]propanoic acid

> <ALOGPS_LOGP>
-2.64

> <JCHEM_LOGP>
-3.3796765186342177

> <ALOGPS_LOGS>
-0.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.8228437022597

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7263415407443627

> <JCHEM_PKA_STRONGEST_BASIC>
8.388610500766903

> <JCHEM_POLAR_SURFACE_AREA>
92.41999999999999

> <JCHEM_REFRACTIVITY>
37.794700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.07e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
D-ala-D-ala

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0150264 ((2r)-2-{[(2r)-2-amino-1-hydroxypropylidene]amino}propanoic acid)

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PDB for NP0150264 ((2r)-2-{[(2r)-2-amino-1-hydroxypropylidene]amino}propanoic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      34.835 -38.580   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      36.169 -40.890   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      40.170 -37.040   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      38.836 -39.350   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      42.837 -38.580   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      37.502 -38.580   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.504 -39.350   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      37.502 -37.040   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      41.504 -40.890   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      36.169 -39.350   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      40.170 -38.580   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    6   11                                                       
CONECT    5    7                                                            
CONECT    6    4    8   10                                                  
CONECT    7    5    9   11                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
CONECT   10    1    2    6                                                  
CONECT   11    3    4    7                                                  
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0150264 ((2r)-2-{[(2r)-2-amino-1-hydroxypropylidene]amino}propanoic acid)
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SMILES for NP0150264 ((2r)-2-{[(2r)-2-amino-1-hydroxypropylidene]amino}propanoic acid)
C[C@@H](N)C(=O)N[C@H](C)C(O)=O
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INCHI for NP0150264 ((2r)-2-{[(2r)-2-amino-1-hydroxypropylidene]amino}propanoic acid)
InChI=1S/C6H12N2O3/c1-3(7)5(9)8-4(2)6(10)11/h3-4H,7H2,1-2H3,(H,8,9)(H,10,11)/t3-,4-/m1/s1
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View in JSmol
Synonyms
ValueSource
(D-Ala)2ChEBI
D-Ala-D-alaChEBI
H-D-Ala-D-ala-OHChEBI
Alanyl-D-alanineHMDB
Ala-alaHMDB
H-Ala-ala-OHHMDB
AlanylalanineHMDB
Alanylalanine, (D)-isomerHMDB
Alanylalanine, (D-ala)-(L-ala)-isomerHMDB
Alanylalanine, (L)-isomerHMDB
Alanylalanine, (L-ala)-(D-ala)-isomerHMDB
Alanylalanine, (L-ala)-(DL-ala)-isomerHMDB
DialanineHMDB
D-Alanyl-L-alanineHMDB
L-Alanyl-D-alanineHMDB
Di-L-alanineHMDB
D-AlanylalanineHMDB
L-Alanyl-L-alanineHMDB
N-D-Alanyl-L-alanineHMDB
N-L-Alanyl-D-alanineHMDB
Chemical FormulaC6H12N2O3
Average Mass160.1711 Da
Monoisotopic Mass160.08479 Da
IUPAC Name(2R)-2-[(2R)-2-aminopropanamido]propanoic acid
Traditional NameD-ala-D-ala
CAS Registry NumberNot Available
SMILES
C[C@@H](N)C(=O)N[C@H](C)C(O)=O
InChI Identifier
InChI=1S/C6H12N2O3/c1-3(7)5(9)8-4(2)6(10)11/h3-4H,7H2,1-2H3,(H,8,9)(H,10,11)/t3-,4-/m1/s1
InChI KeyDEFJQIDDEAULHB-QWWZWVQMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Homo sapiensLOTUS Database
Oryza punctataLOTUS Database
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentDipeptides  
Alternative Parents
Substituents
  • Alpha-dipeptide
    • 

  • N-acyl-alpha-amino acid
    • 

  • N-acyl-alpha amino acid or derivatives
    • 

  • Alpha-amino acid amide
    • 

  • Alanine or derivatives
    • 

  • Alpha-amino acid or derivatives
    • 

  • Amino acid or derivatives
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Amino acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Primary amine
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Amine
    • 

  • 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-2.6ALOGPS
logP-3.4ChemAxon
logS-0.36ALOGPS
pKa (Strongest Acidic)3.73ChemAxon
pKa (Strongest Basic)8.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity37.79 m³·mol⁻¹ChemAxon
Polarizability15.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003459  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003740  
KNApSAcK IDC00019576  
Chemspider ID4573916  
KEGG Compound IDC00993  
BioCyc IDD-ALA-D-ALA  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6937  
PubChem Compound5460362  
PDB IDNot Available
ChEBI ID16576  
Good Scents IDNot Available
References
General References
  1. Ladesic B, Tomasic J, Kveder S, Hrsak I: The metabolic fate of 14C-labeled immunoadjuvant peptidoglycan monomer. II. In vitro studies. Biochim Biophys Acta. 1981 Nov 18;678(1):12-7. [PubMed:6118181  ] 
  2. Franken N, Seidl PH, Kuchenbauer T, Kolb HJ, Schleifer KH, Weiss L, Tympner KD: Specific immunoglobulin A antibodies to a peptide subunit sequence of bacterial cell wall peptidoglycan. Infect Immun. 1984 Apr;44(1):182-7. doi: 10.1128/iai.44.1.182-187.1984. [PubMed:6423541  ] 
  3. Tabata K, Ikeda H, Hashimoto S: ywfE in Bacillus subtilis codes for a novel enzyme, L-amino acid ligase. J Bacteriol. 2005 Aug;187(15):5195-202. doi: 10.1128/JB.187.15.5195-5202.2005. [PubMed:16030213  ] 
  4. Jansen A, Turck M, Szekat C, Nagel M, Clever I, Bierbaum G: Role of insertion elements and yycFG in the development of decreased susceptibility to vancomycin in Staphylococcus aureus. Int J Med Microbiol. 2007 Jul;297(4):205-15. doi: 10.1016/j.ijmm.2007.02.002.  Epub 2007 Apr 5. [PubMed:17418637  ] 
  5. LOTUS database [Link]