NP-MRD: Showing NP-Card for Nopaline (NP0050721)

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Record Information

Version

2.0

Created at

2022-04-27 22:03:29 UTC

Updated at

2022-04-27 22:03:29 UTC

NP-MRD ID

NP0050721

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nopaline

Description

(2S)-2-{[(1R)-4-carbamimidamido-1-carboxybutyl]amino}pentanedioic acid belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on (2S)-2-{[(1R)-4-carbamimidamido-1-carboxybutyl]amino}pentanedioic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282200032D          

 21 20  0  0  1  0            999 V2000
    9.0454    5.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    5.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7599    3.9849    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0454    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6164    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9020    3.9849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4730    3.9849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    2.7474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4743    3.5724    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1888    3.9849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1888    4.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    5.2224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8532    5.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.9033    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6177    3.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0467    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3322    2.7474    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
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 12  1  6  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050721

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H20N4O6/c12-11(13)14-5-1-2-6(9(18)19)15-7(10(20)21)3-4-8(16)17/h6-7,15H,1-5H2,(H,16,17)(H,18,19)(H,20,21)(H4,12,13,14)/t6-,7+/m1/s1

> <INCHI_KEY>
LMKYZBGVKHTLTN-RQJHMYQMSA-N

> <FORMULA>
C11H20N4O6

> <MOLECULAR_WEIGHT>
304.303

> <EXACT_MASS>
304.13828438

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.522254707728624

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(1R)-4-carbamimidamido-1-carboxybutyl]amino}pentanedioic acid

> <ALOGPS_LOGP>
-1.70

> <JCHEM_LOGP>
-5.911055359248211

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.11218605883921

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.504281466517464

> <JCHEM_PKA_STRONGEST_BASIC>
12.075098944574167

> <JCHEM_POLAR_SURFACE_AREA>
185.82999999999998

> <JCHEM_REFRACTIVITY>
80.0666

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nopaline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0      16.885   9.748   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      18.218   8.978   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      19.552   9.748   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      18.218   7.438   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.885   6.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.551   7.438   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.217   6.668   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      12.884   7.438   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      10.216   7.438   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      11.550   5.128   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      19.552   6.668   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      20.886   7.438   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      20.886   8.978   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      22.219   9.748   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      20.259  10.385   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      22.219   6.668   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.553   7.438   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.887   6.668   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      26.220   7.438   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      24.887   5.128   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-{[(1R)-4-carbamimidamido-1-carboxybutyl]amino}pentanedioate	Generator

Chemical Formula

C₁₁H₂₀N₄O₆

Average Mass

304.3030 Da

Monoisotopic Mass

304.13828 Da

IUPAC Name

(2S)-2-{[(1R)-4-carbamimidamido-1-carboxybutyl]amino}pentanedioic acid

Traditional Name

nopaline

CAS Registry Number

Not Available

SMILES

NC(=N)NCCC[C@@H](N[C@@H](CCC(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C11H20N4O6/c12-11(13)14-5-1-2-6(9(18)19)15-7(10(20)21)3-4-8(16)17/h6-7,15H,1-5H2,(H,16,17)(H,18,19)(H,20,21)(H4,12,13,14)/t6-,7+/m1/s1

InChI Key

LMKYZBGVKHTLTN-RQJHMYQMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
Alpha-amino acid
L-alpha-amino acid
D-alpha-amino acid
Tricarboxylic acid or derivatives
Amino fatty acid
Fatty acyl
Guanidine
Amino acid
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Amine
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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	-1.7	ALOGPS
logP	-5.9	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	2.5	ChemAxon
pKa (Strongest Basic)	12.08	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	185.83 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	80.07 m³·mol⁻¹	ChemAxon
Polarizability	28.52 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

390247

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441577

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Nopaline (NP0050721)

MOL for NP0050721 (Nopaline)

3D MOL for NP0050721 (Nopaline)

3D SDF for NP0050721 (Nopaline)

3D-SDF for NP0050721 (Nopaline)

PDB for NP0050721 (Nopaline)

3D PDB for NP0050721 (Nopaline)

SMILES for NP0050721 (Nopaline)

INCHI for NP0050721 (Nopaline)

Structure for NP0050721 (Nopaline)

3D Structure for NP0050721 (Nopaline)