NP-MRD: Showing NP-Card for n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide (NP0163238)

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Record Information

Version

2.0

Created at

2022-09-02 21:48:35 UTC

Updated at

2022-09-02 21:48:35 UTC

NP-MRD ID

NP0163238

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide

Description

3-(3-Bromo-4,5-dihydroxyphenyl)-N-[2-({2-[3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide is found in Aplysinella rhax. 3-(3-Bromo-4,5-dihydroxyphenyl)-N-[2-({2-[3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161506472D          

 37 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161506472D          

 37 38  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0163238

> <DATABASE_NAME>
NP-MRD

> <SMILES>
ON=C(CC1=CC=C(O)C(Br)=C1)C(=O)NCCSSCCNC(=O)C(CC1=CC(O)=C(O)C(Br)=C1)=NO

> <INCHI_IDENTIFIER>
InChI=1S/C22H24Br2N4O7S2/c23-14-7-12(1-2-18(14)29)9-16(27-34)21(32)25-3-5-36-37-6-4-26-22(33)17(28-35)10-13-8-15(24)20(31)19(30)11-13/h1-2,7-8,11,29-31,34-35H,3-6,9-10H2,(H,25,32)(H,26,33)

> <INCHI_KEY>
BOJWQLNXCSQXKS-UHFFFAOYSA-N

> <FORMULA>
C22H24Br2N4O7S2

> <MOLECULAR_WEIGHT>
680.38

> <EXACT_MASS>
677.945317

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
59.46459582356567

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(3-bromo-4,5-dihydroxyphenyl)-N-[2-({2-[3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
3.777817685666665

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.802008108623558

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.21037510305418

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6429366919038824

> <JCHEM_POLAR_SURFACE_AREA>
184.07

> <JCHEM_REFRACTIVITY>
151.06709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.14e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3-bromo-4,5-dihydroxyphenyl)-N-[2-({2-[3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.335 -12.320   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0       1.334 -10.010   0.000  0.00  0.00          Br+0
HETATM   12  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0       8.002 -13.860   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   18  S   UNK     0      12.003 -14.630   0.000  0.00  0.00           S+0
HETATM   19  S   UNK     0      13.337 -13.860   0.000  0.00  0.00           S+0
HETATM   20  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.004 -13.860   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      17.338 -14.630   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      20.005 -14.630   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      20.005 -16.170   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0      18.672 -16.940   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      22.673 -14.630   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      24.006 -13.860   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.340 -14.630   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      26.674 -13.860   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      25.340 -16.170   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      26.674 -16.940   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      24.006 -16.940   0.000  0.00  0.00           C+0
HETATM   36 Br   UNK     0      24.006 -18.480   0.000  0.00  0.00          Br+0
HETATM   37  C   UNK     0      22.673 -16.170   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5                                                       
CONECT   13    3   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   29                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Value	Source
3-(3-Bromo-4,5-dihydroxyphenyl)-N-[2-({2-[3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulphanyl)ethyl]-2-(N-hydroxyimino)propanamide	Generator

Chemical Formula

C₂₂H₂₄Br₂N₄O₇S₂

Average Mass

680.3800 Da

Monoisotopic Mass

677.94532 Da

IUPAC Name

3-(3-bromo-4,5-dihydroxyphenyl)-N-[2-({2-[3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide

Traditional Name

3-(3-bromo-4,5-dihydroxyphenyl)-N-[2-({2-[3-(3-bromo-4-hydroxyphenyl)-2-(N-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-2-(N-hydroxyimino)propanamide

CAS Registry Number

Not Available

SMILES

ON=C(CC1=CC=C(O)C(Br)=C1)C(=O)NCCSSCCNC(=O)C(CC1=CC(O)=C(O)C(Br)=C1)=NO

InChI Identifier

InChI=1S/C22H24Br2N4O7S2/c23-14-7-12(1-2-18(14)29)9-16(27-34)21(32)25-3-5-36-37-6-4-26-22(33)17(28-35)10-13-8-15(24)20(31)19(30)11-13/h1-2,7-8,11,29-31,34-35H,3-6,9-10H2,(H,25,32)(H,26,33)

InChI Key

BOJWQLNXCSQXKS-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
Aplysinella rhax	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
3-halophenol
2-halophenol
3-bromophenol
2-bromophenol
Bromobenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Halobenzene
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Ketoxime
Secondary carboxylic acid amide
Organic disulfide
Carboxamide group
Dialkyldisulfide
Sulfenyl compound
Oxime
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organosulfur compound
Organohalogen compound
Organobromide
Organonitrogen compound
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	3.23	ALOGPS
logP	3.78	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	6.21	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	184.07 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	151.07 m³·mol⁻¹	ChemAxon
Polarizability	59.46 Å³	ChemAxon
Number of Rings	2	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide (NP0163238)

MOL for NP0163238 (n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide)

3D MOL for NP0163238 (n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide)

3D SDF for NP0163238 (n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide)

3D-SDF for NP0163238 (n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide)

PDB for NP0163238 (n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide)

3D PDB for NP0163238 (n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide)

SMILES for NP0163238 (n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide)

INCHI for NP0163238 (n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide)

Structure for NP0163238 (n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide)

3D Structure for NP0163238 (n-[2-({2-[3-(3-bromo-4,5-dihydroxyphenyl)-2-(n-hydroxyimino)propanamido]ethyl}disulfanyl)ethyl]-3-(3-bromo-4-hydroxyphenyl)-2-(n-hydroxyimino)propanamide)