NP-MRD: Showing NP-Card for (2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid (NP0296570)

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Record Information

Version

2.0

Created at

2022-09-10 06:13:38 UTC

Updated at

2022-09-10 06:13:38 UTC

NP-MRD ID

NP0296570

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid

Description

Aeruginosin 298-B 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. (2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid was first documented in 2001 (PMID: 11560314). Based on a literature review very few articles have been published on Aeruginosin 298-B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102208132D          

 33 35  0  0  1  0            999 V2000
    3.1964   -0.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1964    0.1631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4820    0.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9109    0.5756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6254    0.1631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6254   -0.6619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9109   -1.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0904   -1.1606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9109   -1.8994    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6254   -2.3119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1964   -2.3119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1964   -3.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9109   -3.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9109   -4.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1964   -4.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1964   -5.6119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4820   -4.3744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4820   -3.5494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3399    1.4006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0543    0.1631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8080    0.4987    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9795    1.3057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7642    1.5606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3664    1.8577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3600   -0.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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  5 19  1  0  0  0  0
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 32 33  1  0  0  0  0
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 33 21  1  6  0  0  0
M  END

     RDKit          3D

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   -0.5512    4.2459    2.7671 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0442    0.3981    1.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0592   -0.1652   -1.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309102208132D          

 33 35  0  0  1  0            999 V2000
    3.1964   -0.6619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0296570

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@H](N=C(O)[C@H](O)CC1=CC=C(O)C=C1)C(=O)N1[C@@H](C[C@@H]2CC[C@@H](O)C[C@H]12)C(O)=N

> <INCHI_IDENTIFIER>
InChI=1S/C24H35N3O6/c1-13(2)9-18(26-23(32)21(30)10-14-3-6-16(28)7-4-14)24(33)27-19-12-17(29)8-5-15(19)11-20(27)22(25)31/h3-4,6-7,13,15,17-21,28-30H,5,8-12H2,1-2H3,(H2,25,31)(H,26,32)/t15-,17+,18+,19-,20-,21+/m0/s1

> <INCHI_KEY>
FEBDAAYWFMTVBF-XDUBPDLBSA-N

> <FORMULA>
C24H35N3O6

> <MOLECULAR_WEIGHT>
461.559

> <EXACT_MASS>
461.252585859

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.37673491664947

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3aS,6R,7aS)-1-[(2R)-2-{[(2R)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydro-1H-indole-2-carboximidic acid

> <JCHEM_LOGP>
-0.7145274347123189

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.825731921572128

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.7041208744049943

> <JCHEM_PKA_STRONGEST_BASIC>
12.807724168189516

> <JCHEM_POLAR_SURFACE_AREA>
157.67000000000002

> <JCHEM_REFRACTIVITY>
132.51680000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3aS,6R,7aS)-1-[(2R)-2-{[(2R)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       5.967  -1.235   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.967   0.305   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.633   1.075   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.300   1.075   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.634   0.305   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       8.634  -1.235   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.300  -2.005   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.769  -2.166   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.300  -3.545   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.634  -4.315   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.967  -4.315   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.967  -5.855   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.300  -6.625   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.300  -8.165   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.967  -8.935   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.967 -10.475   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.633  -8.165   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.633  -6.625   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.968   1.075   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.968   2.615   0.000  0.00  0.00           O+0
HETATM   21  N   UNK     0      11.301   0.305   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0      12.708   0.931   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.028   2.437   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0      14.493   2.913   0.000  0.00  0.00           N+0
HETATM   25  O   UNK     0      11.884   3.468   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.739  -0.214   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.969  -1.547   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.445  -3.012   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.414  -4.156   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.908  -3.836   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.877  -4.981   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.432  -2.371   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.462  -1.227   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   12                                                       
CONECT   19    5   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   33                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   22   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27   21                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₅N₃O₆

Average Mass

461.5590 Da

Monoisotopic Mass

461.25259 Da

IUPAC Name

(2S,3aS,6R,7aS)-1-[(2R)-2-{[(2R)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydro-1H-indole-2-carboximidic acid

Traditional Name

(2S,3aS,6R,7aS)-1-[(2R)-2-{[(2R)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@H](N=C(O)[C@H](O)CC1=CC=C(O)C=C1)C(=O)N1[C@@H](C[C@@H]2CC[C@@H](O)C[C@H]12)C(O)=N

InChI Identifier

InChI=1S/C24H35N3O6/c1-13(2)9-18(26-23(32)21(30)10-14-3-6-16(28)7-4-14)24(33)27-19-12-17(29)8-5-15(19)11-20(27)22(25)31/h3-4,6-7,13,15,17-21,28-30H,5,8-12H2,1-2H3,(H2,25,31)(H,26,32)/t15-,17+,18+,19-,20-,21+/m0/s1

InChI Key

FEBDAAYWFMTVBF-XDUBPDLBSA-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

Not Available

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
Leucine or derivatives
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Indole or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Cyclic alcohol
Primary carboxylic acid amide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Organoheterocyclic compound
Azacycle
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	-0.71	ChemAxon
pKa (Strongest Acidic)	-1.7	ChemAxon
pKa (Strongest Basic)	12.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	157.67 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	132.52 m³·mol⁻¹	ChemAxon
Polarizability	49.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

C00027063

Chemspider ID

60169376

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102376881

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Valls N, Lopez-Canet M, Vallribera M, Bonjoch J: First total syntheses of aeruginosin 298-A and aeruginosin 298-B, based on a stereocontrolled route to the new amino acid 6-hydroxyoctahydroindole-2-carboxylic acid. Chemistry. 2001 Aug 17;7(16):3446-60. doi: 10.1002/1521-3765(20010817)7:16<3446::aid-chem3446>3.0.co;2-0. [PubMed:11560314 ]
LOTUS database [Link]

Showing NP-Card for (2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid (NP0296570)

MOL for NP0296570 ((2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid)

3D MOL for NP0296570 ((2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid)

3D SDF for NP0296570 ((2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid)

3D-SDF for NP0296570 ((2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid)

PDB for NP0296570 ((2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid)

3D PDB for NP0296570 ((2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid)

SMILES for NP0296570 ((2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid)

INCHI for NP0296570 ((2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid)

Structure for NP0296570 ((2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid)

3D Structure for NP0296570 ((2s,3as,6r,7as)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl]-6-hydroxy-octahydroindole-2-carboximidic acid)