NP-MRD: Showing NP-Card for (2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid (NP0197328)

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Record Information

Version

2.0

Created at

2022-09-04 15:34:37 UTC

Updated at

2022-09-04 15:34:37 UTC

NP-MRD ID

NP0197328

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid

Description

NSC614495 belongs to the class of organic compounds known as o-bromophenols. These are bromophenols carrying a iodine at the C2 position of the benzene ring. (2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid is found in Aplysinella rhax. Based on a literature review very few articles have been published on NSC614495.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217342D          

 36 37  0  0  0  0            999 V2000
   -4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302   -7.0125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0013   -6.1875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309042217342D          

 36 37  0  0  0  0            999 V2000
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   -4.2868   -5.7750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2868   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0197328

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O\N=C(\CC1=CC=C(O)C(Br)=C1)C(O)=NCCSSCCN=C(O)C(\CC1=CC=C(O)C(Br)=C1)=N/O

> <INCHI_IDENTIFIER>
InChI=1S/C22H24Br2N4O6S2/c23-15-9-13(1-3-19(15)29)11-17(27-33)21(31)25-5-7-35-36-8-6-26-22(32)18(28-34)12-14-2-4-20(30)16(24)10-14/h1-4,9-10,29-30,33-34H,5-8,11-12H2,(H,25,31)(H,26,32)/b27-17-,28-18-

> <INCHI_KEY>
LMAFSGDNHVBIHU-HJTNQMAYSA-N

> <FORMULA>
C22H24Br2N4O6S2

> <MOLECULAR_WEIGHT>
664.38

> <EXACT_MASS>
661.950403

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
58.542355233544896

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-3-(3-bromo-4-hydroxyphenyl)-N-{2-[(2-{[(2Z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(N-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(N-hydroxyimino)propanimidic acid

> <JCHEM_LOGP>
4.72688951811876

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.4281774575149067

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.511207434834068

> <JCHEM_PKA_STRONGEST_BASIC>
3.968553586201781

> <JCHEM_POLAR_SURFACE_AREA>
170.82000000000002

> <JCHEM_REFRACTIVITY>
150.12959999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-(3-bromo-4-hydroxyphenyl)-N-{2-[(2-{[(2Z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(N-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(N-hydroxyimino)propanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      -8.002 -10.780   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668 -13.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -8.002 -15.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.336 -16.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -10.669 -15.400   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0     -12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0     -10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0     -12.003 -13.090   0.000  0.00  0.00          Br+0
HETATM   12  C   UNK     0      -9.336 -13.090   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      -4.001 -11.550   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0      -2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   18  S   UNK     0       0.000 -10.780   0.000  0.00  0.00           S+0
HETATM   19  S   UNK     0       1.334 -11.550   0.000  0.00  0.00           S+0
HETATM   20  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       5.335 -10.780   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.668 -13.090   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.669  -6.160   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      13.337  -6.160   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003  -8.470   0.000  0.00  0.00           C+0
HETATM   33 Br   UNK     0      13.337  -9.240   0.000  0.00  0.00          Br+0
HETATM   34  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       9.336 -11.550   0.000  0.00  0.00           N+0
HETATM   36  O   UNK     0       9.336 -13.090   0.000  0.00  0.00           O+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   35                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   27                                                       
CONECT   35   25   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₄Br₂N₄O₆S₂

Average Mass

664.3800 Da

Monoisotopic Mass

661.95040 Da

IUPAC Name

(2Z)-3-(3-bromo-4-hydroxyphenyl)-N-{2-[(2-{[(2Z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(N-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(N-hydroxyimino)propanimidic acid

Traditional Name

(2Z)-3-(3-bromo-4-hydroxyphenyl)-N-{2-[(2-{[(2Z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(N-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(N-hydroxyimino)propanimidic acid

CAS Registry Number

Not Available

SMILES

O\N=C(\CC1=CC=C(O)C(Br)=C1)C(O)=NCCSSCCN=C(O)C(\CC1=CC=C(O)C(Br)=C1)=N/O

InChI Identifier

InChI=1S/C22H24Br2N4O6S2/c23-15-9-13(1-3-19(15)29)11-17(27-33)21(31)25-5-7-35-36-8-6-26-22(32)18(28-34)12-14-2-4-20(30)16(24)10-14/h1-4,9-10,29-30,33-34H,5-8,11-12H2,(H,25,31)(H,26,32)/b27-17-,28-18-

InChI Key

LMAFSGDNHVBIHU-HJTNQMAYSA-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 o-bromophenols. These are bromophenols carrying a iodine at the C2 position of the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

2-bromophenol
1-hydroxy-2-unsubstituted benzenoid
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Fatty acyl
Fatty amide
Ketoxime
Dialkyldisulfide
Carboxamide group
Secondary carboxylic acid amide
Organic disulfide
Sulfenyl compound
Carboxylic acid derivative
Oxime
Organooxygen compound
Organosulfur compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organohalogen compound
Organobromide
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	4.73	ChemAxon
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	3.97	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	150.13 m³·mol⁻¹	ChemAxon
Polarizability	58.54 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

4911841

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6399893

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid (NP0197328)

MOL for NP0197328 ((2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid)

3D MOL for NP0197328 ((2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid)

3D SDF for NP0197328 ((2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid)

3D-SDF for NP0197328 ((2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid)

PDB for NP0197328 ((2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid)

3D PDB for NP0197328 ((2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid)

SMILES for NP0197328 ((2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid)

INCHI for NP0197328 ((2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid)

Structure for NP0197328 ((2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid)

3D Structure for NP0197328 ((2z)-3-(3-bromo-4-hydroxyphenyl)-n-{2-[(2-{[(2z)-3-(3-bromo-4-hydroxyphenyl)-1-hydroxy-2-(n-hydroxyimino)propylidene]amino}ethyl)disulfanyl]ethyl}-2-(n-hydroxyimino)propanimidic acid)