NP-MRD: Showing NP-Card for Canavaninosuccinate (NP0091974)

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Record Information

Version

2.0

Created at

2022-05-11 18:53:36 UTC

Updated at

2022-05-11 18:53:37 UTC

NP-MRD ID

NP0091974

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Canavaninosuccinate

Description

Canavaninosuccinate belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Synthesis of canavaninosuccinate was strongly inhibited by added argininosuccinate, less so by canavaninosuccinate, arginine, canavanine, glycine, or 2,3-dimercaptopropanol. Canavaninosuccinate is a very strong basic compound (based on its pKa). Outside of the human body, Canavaninosuccinate has been detected, but not quantified in, several different foods, such as lemon grass, small-leaf lindens, jew's ears, anises, and bog bilberries. This could make canavaninosuccinate a potential biomarker for the consumption of these foods. Subsequent addition of dithiothreitol in the presence of Fe2+ resulted in the cleavage of some of the synthesized canavaninosuccinate to form guanidinosuccinate and homoserine. All the reactions, starting with canavaninosuccinate and down to the formation of guanidinoacetate and guanidinosuccinate have been demonstrated in human tissue ( (PMID: 241511 ). Canavaninosuccinate is formed from ureidohomoserine and aspartate by a human or bovine liver extract that had high argininosuccinate synthetase (EC6.3.4.5) Activity, and the subsequent formation of guanidinosuccinate is done by reductive cleavage. In the presence of ATP the optimum pH for the synthetic reaction is 8.4. Canavaninosuccinate was first documented in 1975 (PMID: 241511). This reaction can be carried out in either a tris(hydroxymethyl)aminomethane or borate buffer.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 35  0  0  0  0  0  0  0  0999 V2000
    0.2758    1.3542   -1.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6383    1.2741   -1.3305 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8418    0.3403   -0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2314   -0.5859   -0.2216 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1429   -0.3724    0.7241 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3666   -0.1117    0.0596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4590    0.1394    1.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7456    0.4519    0.3431 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7470    0.6991    1.4031 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1754   -0.6634   -0.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1690   -1.3919   -0.1895 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5311   -0.9764   -1.6683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0261    0.1263    0.2357 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3442   -0.1194   -0.2944 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2367   -0.5458    0.8451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6121   -0.8669    0.4721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4233   -1.0656    1.4372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1336   -0.9810   -0.7923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8547    1.1324   -0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1203    1.9405   -1.5132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2104    1.4102   -0.8420 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2534   -1.4400   -0.8173 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5818   -0.9564   -0.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2476    0.7865   -0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599   -0.8063    1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1548    0.9634    1.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5980    1.4030   -0.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5247    0.0203    2.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5779    1.6787    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3620   -1.9732   -1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9474    0.1527    1.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2417   -0.9172   -1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7849   -1.4882    1.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1402    0.2222    1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5805   -1.1921   -1.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5681    2.3589   -0.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  3 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
 14 19  1  0
 19 21  1  0
 19 20  2  0
  8 10  1  0
 10 12  1  0
 10 11  2  0
  9 28  1  0
  9 29  1  0
  8 27  1  6
  7 25  1  0
  7 26  1  0
  6 23  1  0
  6 24  1  0
  4 22  1  0
  2  1  1  0
 13 31  1  0
 14 32  1  6
 15 33  1  0
 15 34  1  0
 18 35  1  0
 21 36  1  0
 12 30  1  0
M  END


  Mrv0541 02241203492D          

 20 19  0  0  0  0            999 V2000
    6.8071   -5.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5215   -4.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2361   -6.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0926   -4.9805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9505   -6.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5215   -6.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3781   -5.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9505   -7.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6650   -5.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0926   -4.1555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3795   -4.9805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6650   -6.2180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9505   -4.9805    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5215   -7.4555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8071   -6.2180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6636   -4.9805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3781   -6.2180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6650   -7.8680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2361   -7.8680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2361   -5.3930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  2  1  0  0  0  0
  2 20  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4 10  1  0  0  0  0
  4  7  1  0  0  0  0
  5 12  1  0  0  0  0
  5  8  1  0  0  0  0
  6 14  1  0  0  0  0
  6 15  2  0  0  0  0
  7 16  1  0  0  0  0
  7 17  2  0  0  0  0
  8 18  1  0  0  0  0
  8 19  2  0  0  0  0
  9 13  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 13 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0091974

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N4O7/c10-4(7(16)17)1-2-20-13-9(11)12-5(8(18)19)3-6(14)15/h4-5H,1-3,10H2,(H,14,15)(H,16,17)(H,18,19)(H3,11,12,13)

> <INCHI_KEY>
SGYMGUGIGTWWLU-UHFFFAOYSA-N

> <FORMULA>
C9H16N4O7

> <MOLECULAR_WEIGHT>
292.2459

> <EXACT_MASS>
292.101898886

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
26.744557922026736

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[3-(3-amino-3-carboxypropoxy)carbamimidamido]butanedioic acid

> <ALOGPS_LOGP>
-3.34

> <JCHEM_LOGP>
-6.1310713132245755

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.0414124792542925

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8968638446408148

> <JCHEM_PKA_STRONGEST_BASIC>
10.328879085982145

> <JCHEM_POLAR_SURFACE_AREA>
195.05999999999997

> <JCHEM_REFRACTIVITY>
82.63209999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[3-(3-amino-3-carboxypropoxy)carbamimidamido]butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      12.707 -10.067   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.040  -9.297   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.374 -11.607   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.373  -9.297   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.708 -12.377   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.040 -12.377   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.039 -10.067   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.708 -13.917   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.041 -10.067   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      11.373  -7.757   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      19.375  -9.297   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      18.041 -11.607   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      16.708  -9.297   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0      14.040 -13.917   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      12.707 -11.607   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.705  -9.297   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.039 -11.607   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      18.041 -14.687   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      15.374 -14.687   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      15.374 -10.067   0.000  0.00  0.00           O+0
CONECT    1    4    2                                                       
CONECT    2    1   20                                                       
CONECT    3    5    6                                                       
CONECT    4    1   10    7                                                  
CONECT    5    3   12    8                                                  
CONECT    6    3   14   15                                                  
CONECT    7    4   16   17                                                  
CONECT    8    5   18   19                                                  
CONECT    9   13   11   12                                                  
CONECT   10    4                                                            
CONECT   11    9                                                            
CONECT   12    5    9                                                       
CONECT   13    9   20                                                       
CONECT   14    6                                                            
CONECT   15    6                                                            
CONECT   16    7                                                            
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19    8                                                            
CONECT   20    2   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
Canavaninosuccinic acid	Generator
2-[N'-(3-amino-3-carboxypropoxy)carbamimidamido]butanedioate	HMDB

Chemical Formula

C₉H₁₆N₄O₇

Average Mass

292.2459 Da

Monoisotopic Mass

292.10190 Da

IUPAC Name

2-[3-(3-amino-3-carboxypropoxy)carbamimidamido]butanedioic acid

Traditional Name

2-[3-(3-amino-3-carboxypropoxy)carbamimidamido]butanedioic acid

CAS Registry Number

Not Available

SMILES

NC(CCONC(=N)NC(CC(O)=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C9H16N4O7/c10-4(7(16)17)1-2-20-13-9(11)12-5(8(18)19)3-6(14)15/h4-5H,1-3,10H2,(H,14,15)(H,16,17)(H,18,19)(H3,11,12,13)

InChI Key

SGYMGUGIGTWWLU-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspartic acid and derivatives. Aspartic acid and derivatives are compounds containing an aspartic acid or a derivative thereof resulting from reaction of aspartic 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

Aspartic acid and derivatives

Alternative Parents

Substituents

Aspartic acid or derivatives
Alpha-amino acid
Tricarboxylic acid or derivatives
Guanidine
Amino acid
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Carboxylic acid
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Organopnictogen compound
Organic oxide
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	-3.3	ALOGPS
logP	-6.1	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	1.9	ChemAxon
pKa (Strongest Basic)	10.33	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.06 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	82.63 m³·mol⁻¹	ChemAxon
Polarizability	26.74 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

HMDB0012197

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB028845

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CANAVANINOSUCCINATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

25201068

PDB ID

Not Available

ChEBI ID

89639

Good Scents ID

Not Available

References

General References

Koller A, Aldwin L, Natelson S: Hepatic synthesis of canavaninosuccinate from ureidohomoserine and aspartate, and its conversion to guanidinosuccinate. Clin Chem. 1975 Nov;21(12):1777-82. [PubMed:241511 ]

Showing NP-Card for Canavaninosuccinate (NP0091974)

MOL for NP0091974 (Canavaninosuccinate)

3D MOL for NP0091974 (Canavaninosuccinate)

3D SDF for NP0091974 (Canavaninosuccinate)

3D-SDF for NP0091974 (Canavaninosuccinate)

PDB for NP0091974 (Canavaninosuccinate)

3D PDB for NP0091974 (Canavaninosuccinate)

SMILES for NP0091974 (Canavaninosuccinate)

INCHI for NP0091974 (Canavaninosuccinate)

Structure for NP0091974 (Canavaninosuccinate)

3D Structure for NP0091974 (Canavaninosuccinate)