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Showing NP-Card for cyanoalanine (NP0223472)

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Record Information
Version1.0
Created at2022-09-06 01:34:56 UTC
Updated at2022-09-06 01:34:56 UTC
NP-MRD IDNP0223472
Secondary Accession NumbersNone
Natural Product Identification
Common Namecyanoalanine
Description cyanoalanine is found in Clitocybe acromelalga and Vicia sativa. It was first documented in 2016 (PMID: 26714205).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0223472 (cyanoalanine)

Structure #1
  Mrv0541 02241206582D          

  8  7  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    1.5395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    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
  2  5  3  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
M  END
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3D MOL for NP0223472 (cyanoalanine)

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3D SDF for NP0223472 (cyanoalanine)
Structure #1
  Mrv0541 02241206582D          

  8  7  0  0  0  0            999 V2000
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    1.5395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.9520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    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
  2  5  3  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  2  0  0  0  0
  4  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0223472

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CC#N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H6N2O2/c5-2-1-3(6)4(7)8/h3H,1,6H2,(H,7,8)

> <INCHI_KEY>
BXRLWGXPSRYJDZ-UHFFFAOYSA-N

> <FORMULA>
C4H6N2O2

> <MOLECULAR_WEIGHT>
114.1026

> <EXACT_MASS>
114.042927446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
10.325359759626444

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-3-cyanopropanoic acid

> <ALOGPS_LOGP>
-2.38

> <JCHEM_LOGP>
-3.4166663678427383

> <ALOGPS_LOGS>
-0.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.22908298380166503

> <JCHEM_PKA_STRONGEST_BASIC>
7.228347482869566

> <JCHEM_POLAR_SURFACE_AREA>
87.11

> <JCHEM_REFRACTIVITY>
25.512

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-3-cyanopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0223472 (cyanoalanine)
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PDB for NP0223472 (cyanoalanine)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.310   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  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.357   2.874   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    4    6                                                  
CONECT    4    3    7    8                                                  
CONECT    5    2                                                            
CONECT    6    3                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0223472 (cyanoalanine)
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SMILES for NP0223472 (cyanoalanine)
NC(CC#N)C(O)=O
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INCHI for NP0223472 (cyanoalanine)
InChI=1S/C4H6N2O2/c5-2-1-3(6)4(7)8/h3H,1,6H2,(H,7,8)
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Synonyms
ValueSource
CyanoalanineChEBI
PropargylglycineChEBI
b-CyanoalanineGenerator
Β-cyanoalanineGenerator
3-CyanoalanineMeSH
beta-cyano-D-AlanineMeSH
beta-cyano-L-AlanineMeSH
3-Cyanoalanine, (L)-isomerMeSH
3-Cyanoalanine, (D)-isomerMeSH
Chemical FormulaC4H6N2O2
Average Mass114.1026 Da
Monoisotopic Mass114.04293 Da
IUPAC Name2-amino-3-cyanopropanoic acid
Traditional Name2-amino-3-cyanopropanoic acid
CAS Registry NumberNot Available
SMILES
NC(CC#N)C(O)=O
InChI Identifier
InChI=1S/C4H6N2O2/c5-2-1-3(6)4(7)8/h3H,1,6H2,(H,7,8)
InChI KeyBXRLWGXPSRYJDZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Clitocybe acromelalgaLOTUS Database
Vicia sativaLOTUS Database
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
    • 

  • Fatty acid
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carbonitrile
    • 

  • Nitrile
    • 

  • Organic nitrogen compound
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Amine
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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-2.4ALOGPS
logP-3.4ChemAxon
logS-0.56ALOGPS
pKa (Strongest Acidic)0.23ChemAxon
pKa (Strongest Basic)7.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.11 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity25.51 m³·mol⁻¹ChemAxon
Polarizability10.33 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB007482  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13538  
PDB IDNot Available
ChEBI ID132546  
Good Scents IDNot Available
References
General References
  1. van Ohlen M, Herfurth AM, Kerbstadt H, Wittstock U: Cyanide detoxification in an insect herbivore: Molecular identification of beta-cyanoalanine synthases from Pieris rapae. Insect Biochem Mol Biol. 2016 Mar;70:99-110. doi: 10.1016/j.ibmb.2015.12.004.  Epub 2015 Dec 20. [PubMed:26714205  ] 
  2. Ghasemi N, Secen H, Yilmaz H, Binici B, Goren AC: Determination of neurotoxic agents as markers of common vetch adulteration in lentil by LC-MS/MS. Food Chem. 2017 Apr 15;221:2005-2009. doi: 10.1016/j.foodchem.2016.11.079. Epub  2016 Nov 24. [PubMed:27979192  ] 
  3. LOTUS database [Link]