NP-MRD: Showing NP-Card for 2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid (NP0225081)

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Record Information

Version

2.0

Created at

2022-09-06 03:41:40 UTC

Updated at

2022-09-06 03:41:40 UTC

NP-MRD ID

NP0225081

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid

Description

2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid is found in Clitocybe acromelalga.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 29  0  0  0  0  0  0  0  0999 V2000
   -0.7801    1.6682    3.2631 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5832    1.5234    2.4307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5998    1.3536    1.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4817   -0.0761    0.8460 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1710   -0.2287    0.3111 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7116   -1.2060   -0.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4962   -2.3079   -0.6227 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6836   -1.1908   -0.8216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3363    0.0880   -0.4057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7618    0.0715   -0.9120 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4064   -1.0859   -0.2977 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4889    1.3128   -0.5675 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4918    1.2508    0.1504 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0496    2.5223   -1.0439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5622   -0.3050   -0.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7468   -0.1891    0.2737 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3638   -0.6435   -1.4544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3710    2.0155    0.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6010    1.5417    1.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6746   -0.7328    1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5401   -3.0932   -0.0067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2622   -2.0674   -0.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6419   -1.2464   -1.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3068    0.1776    0.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7609    0.9401   -0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7526   -0.0136   -2.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3183   -1.2248   -0.8055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6893   -0.7711    0.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7485    3.2471   -0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0158   -1.3303   -1.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  0
  6  5  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  3  0
  4 15  1  0
 15 17  1  0
 15 16  2  0
 10 12  1  0
 12 14  1  0
 12 13  2  0
 11 27  1  0
 11 28  1  0
 10 26  1  6
  9 24  1  0
  9 25  1  0
  8 22  1  0
  8 23  1  0
  7 21  1  0
  4 20  1  1
  3 18  1  0
  3 19  1  0
 17 30  1  0
 14 29  1  0
M  END

Structure #1
  Mrv0541 02241207012D          

 17 16  0  0  0  0            999 V2000
    3.3809    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    4.4270    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    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    4.8395    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
    1.2375   -0.9355    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    4.8395    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    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0954    5.6645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099    4.4270    0.0000 O   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  5  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  1  0  0  0  0
  4 10  3  0  0  0  0
  5  8  1  0  0  0  0
  5 11  1  0  0  0  0
  6  9  1  0  0  0  0
 12  6  1  4  0  0  0
  7 12  2  0  0  0  0
  7 13  1  0  0  0  0
  8 14  2  0  0  0  0
  8 15  1  0  0  0  0
  9 16  2  0  0  0  0
  9 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225081

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H13N3O5/c10-4-3-6(9(16)17)12-7(13)2-1-5(11)8(14)15/h5-6H,1-3,11H2,(H,12,13)(H,14,15)(H,16,17)

> <INCHI_KEY>
QUAADUAOVLZBJM-UHFFFAOYSA-N

> <FORMULA>
C9H13N3O5

> <MOLECULAR_WEIGHT>
243.2166

> <EXACT_MASS>
243.085520541

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
22.819512129208057

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-[(1-carboxy-2-cyanoethyl)-C-hydroxycarbonimidoyl]butanoic acid

> <ALOGPS_LOGP>
-3.14

> <JCHEM_LOGP>
-3.6080873277942107

> <ALOGPS_LOGS>
-1.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.4242506375904784

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3562283540532833

> <JCHEM_PKA_STRONGEST_BASIC>
9.537515643281333

> <JCHEM_POLAR_SURFACE_AREA>
157

> <JCHEM_REFRACTIVITY>
54.121500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-glutamyl-β-cyanoalanine

> <JCHEM_VEBER_RULE>
0

$$$$

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       6.311   6.724   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.977   5.954   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.311   8.264   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977   4.414   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.645   9.034   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.310  -1.746   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       4.977   9.034   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       3.644   3.644   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       6.311   3.644   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       7.645  10.574   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.978   8.264   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    7                                                       
CONECT    3    4    6                                                       
CONECT    4    3   10                                                       
CONECT    5    1    8   11                                                  
CONECT    6    3    9   12                                                  
CONECT    7    2   12   13                                                  
CONECT    8    5   14   15                                                  
CONECT    9    6   16   17                                                  
CONECT   10    4                                                            
CONECT   11    5                                                            
CONECT   12    6    7                                                       
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17    9                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
g-Glutamyl-b-cyanoalanine	Generator
Γ-glutamyl-β-cyanoalanine	Generator

Chemical Formula

C₉H₁₃N₃O₅

Average Mass

243.2166 Da

Monoisotopic Mass

243.08552 Da

IUPAC Name

2-amino-4-[(1-carboxy-2-cyanoethyl)-C-hydroxycarbonimidoyl]butanoic acid

Traditional Name

gamma-glutamyl-β-cyanoalanine

CAS Registry Number

Not Available

SMILES

NC(CCC(O)=NC(CC#N)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C9H13N3O5/c10-4-3-6(9(16)17)12-7(13)2-1-5(11)8(14)15/h5-6H,1-3,11H2,(H,12,13)(H,14,15)(H,16,17)

InChI Key

QUAADUAOVLZBJM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Clitocybe acromelalga	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Gamma-glutamyl alpha-amino acid
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid
Alpha-amino acid or derivatives
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Fatty amide
N-acyl-amine
Amino acid or derivatives
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Nitrile
Carbonitrile
Primary aliphatic amine
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Amine
Organonitrogen compound
Organic nitrogen compound
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3.1	ALOGPS
logP	-3.6	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	1.36	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	157 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	54.12 m³·mol⁻¹	ChemAxon
Polarizability	22.82 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440768

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid (NP0225081)

MOL for NP0225081 (2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D MOL for NP0225081 (2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D SDF for NP0225081 (2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D-SDF for NP0225081 (2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

PDB for NP0225081 (2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D PDB for NP0225081 (2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

SMILES for NP0225081 (2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

INCHI for NP0225081 (2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

Structure for NP0225081 (2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D Structure for NP0225081 (2-amino-4-[(1-carboxy-2-cyanoethyl)-c-hydroxycarbonimidoyl]butanoic acid)