NP-MRD: Showing NP-Card for (e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid (NP0311190)

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Record Information

Version

2.0

Created at

2022-09-11 07:01:34 UTC

Updated at

2022-09-11 07:01:34 UTC

NP-MRD ID

NP0311190

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid

Description

Tunichrome An-3 belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another. (e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid is found in Ascidia ceratodes and Phallusia nigra. Based on a literature review very few articles have been published on Tunichrome An-3.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112209012D          

 38 40  0  0  1  0            999 V2000
    5.0013   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309112209012D          

 38 40  0  0  1  0            999 V2000
    5.0013   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 31 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0311190

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC1=CC=C(O)C(O)=C1)C(O)=N\C(=C/C1=CC(O)=C(O)C(O)=C1)\C(\O)=N/C=C/C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H25N3O9/c27-16(7-14-2-4-19(31)21(33)10-14)25(37)29-17(8-15-11-22(34)24(36)23(35)12-15)26(38)28-6-5-13-1-3-18(30)20(32)9-13/h1-6,8-12,16,30-36H,7,27H2,(H,28,38)(H,29,37)/b6-5+,17-8-/t16-/m0/s1

> <INCHI_KEY>
YZJCCLAFSMNGFH-ULSDBDNISA-N

> <FORMULA>
C26H25N3O9

> <MOLECULAR_WEIGHT>
523.498

> <EXACT_MASS>
523.159079397

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
52.409267547145284

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(E,2Z)-2-{[(2S)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-N-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid

> <JCHEM_LOGP>
0.8684031640957093

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
6.939266461352178

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9737926593889417

> <JCHEM_PKA_STRONGEST_BASIC>
9.314443677584446

> <JCHEM_POLAR_SURFACE_AREA>
232.80999999999995

> <JCHEM_REFRACTIVITY>
139.6905

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(E,2Z)-2-{[(2S)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-N-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  N   UNK     0       9.336  -5.390   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      12.003  -2.310   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.672   0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      17.338  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      18.672  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.004  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   28  N   UNK     0      10.669   1.540   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.670   6.930   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      16.004   6.160   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      17.338   6.930   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      17.338   3.850   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   26                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   17                                                       
CONECT   26   15   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   38                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   31                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₅N₃O₉

Average Mass

523.4980 Da

Monoisotopic Mass

523.15908 Da

IUPAC Name

(E,2Z)-2-{[(2S)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-N-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid

Traditional Name

(E,2Z)-2-{[(2S)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-N-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CC1=CC=C(O)C(O)=C1)C(O)=N\C(=C/C1=CC(O)=C(O)C(O)=C1)\C(\O)=N/C=C/C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C26H25N3O9/c27-16(7-14-2-4-19(31)21(33)10-14)25(37)29-17(8-15-11-22(34)24(36)23(35)12-15)26(38)28-6-5-13-1-3-18(30)20(32)9-13/h1-6,8-12,16,30-36H,7,27H2,(H,28,38)(H,29,37)/b6-5+,17-8-/t16-/m0/s1

InChI Key

YZJCCLAFSMNGFH-ULSDBDNISA-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
Ascidia ceratodes	LOTUS Database	35616633
Phallusia nigra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as peptides. Peptides are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Peptides

Alternative Parents

Substituents

Alpha peptide
Tyrosine or derivatives
Phenylalanine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid amide
Alpha-amino acid or derivatives
Amphetamine or derivatives
Benzenetriol
Pyrogallol derivative
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Fatty acyl
Fatty amide
Monocyclic benzene moiety
Benzenoid
Amino acid or derivatives
Secondary carboxylic acid amide
Carboxamide group
Polyol
Primary amine
Amine
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	0.87	ChemAxon
pKa (Strongest Acidic)	2.97	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	232.81 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	139.69 m³·mol⁻¹	ChemAxon
Polarizability	52.41 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

10472274

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23426397

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid (NP0311190)

MOL for NP0311190 ((e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid)

3D MOL for NP0311190 ((e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid)

3D SDF for NP0311190 ((e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid)

3D-SDF for NP0311190 ((e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid)

PDB for NP0311190 ((e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid)

3D PDB for NP0311190 ((e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid)

SMILES for NP0311190 ((e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid)

INCHI for NP0311190 ((e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid)

Structure for NP0311190 ((e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid)

3D Structure for NP0311190 ((e,2z)-2-{[(2s)-2-amino-3-(3,4-dihydroxyphenyl)-1-hydroxypropylidene]amino}-n-[(1e)-2-(3,4-dihydroxyphenyl)ethenyl]-3-(3,4,5-trihydroxyphenyl)prop-2-enimidic acid)