NP-MRD: Showing NP-Card for Pyrrolomycin B (NP0022115)

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Record Information

Version

1.0

Created at

2021-01-06 07:20:21 UTC

Updated at

2021-07-15 17:38:10 UTC

NP-MRD ID

NP0022115

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyrrolomycin B

Provided By

NPAtlas

Description

2,4-Dichloro-6-[(4,5-dichloro-3-nitro-1H-pyrrol-2-yl)methyl]phenol belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it. Pyrrolomycin B is found in Streptomyces sp. It was first documented in 1981 (PMID: 7309630). Based on a literature review very few articles have been published on 2,4-dichloro-6-[(4,5-dichloro-3-nitro-1H-pyrrol-2-yl)methyl]phenol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105213D          

 26 27  0  0  0  0            999 V2000
   -1.3847   -1.8470    1.6254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8983   -1.8714    0.4904 N   0  3  0  0  0  4  0  0  0  0  0  0
   -2.2915   -3.0910    0.0116 O   0  5  0  0  0  1  0  0  0  0  0  0
   -2.0673   -0.6309   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1957    0.0985   -0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946   -0.1223   -1.3362 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2319    0.0823   -0.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465    1.3746   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6754    1.6490    0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216    3.2616    1.0785 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1215    0.6322    1.6483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6341   -0.6531    1.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2005   -1.9492    2.5128 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6862   -0.9102    0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840   -2.2284    0.3936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8517    1.2235   -1.3715 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1010    1.1877   -0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3225    2.4274   -1.1992 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2993    0.0554   -0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7352   -0.4740    0.6769 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2105   -1.1859   -1.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4133    0.4868   -2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4036    2.1803   -0.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8610    0.7987    2.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6332   -2.5000   -0.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4705    2.0056   -1.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19  4  1  0  0  0  0
 14  7  1  0  0  0  0
  6 21  1  0  0  0  0
  6 22  1  0  0  0  0
  8 23  1  0  0  0  0
 11 24  1  0  0  0  0
 15 25  1  0  0  0  0
 16 26  1  0  0  0  0
M  CHG  2   2   1   3  -1
M  END


  Mrv1652306242105213D          

 26 27  0  0  0  0            999 V2000
   -1.3847   -1.8470    1.6254 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8983   -1.8714    0.4904 N   0  3  0  0  0  4  0  0  0  0  0  0
   -2.2915   -3.0910    0.0116 O   0  5  0  0  0  1  0  0  0  0  0  0
   -2.0673   -0.6309   -0.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1957    0.0985   -0.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1946   -0.1223   -1.3362 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2319    0.0823   -0.3424 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465    1.3746   -0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6754    1.6490    0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3216    3.2616    1.0785 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1215    0.6322    1.6483 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6341   -0.6531    1.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2005   -1.9492    2.5128 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6862   -0.9102    0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2840   -2.2284    0.3936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8517    1.2235   -1.3715 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1010    1.1877   -0.9005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3225    2.4274   -1.1992 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2993    0.0554   -0.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7352   -0.4740    0.6769 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2105   -1.1859   -1.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4133    0.4868   -2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4036    2.1803   -0.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8610    0.7987    2.4453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6332   -2.5000   -0.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4705    2.0056   -1.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19  4  1  0  0  0  0
 14  7  1  0  0  0  0
  6 21  1  0  0  0  0
  6 22  1  0  0  0  0
  8 23  1  0  0  0  0
 11 24  1  0  0  0  0
 15 25  1  0  0  0  0
 16 26  1  0  0  0  0
M  CHG  2   2   1   3  -1
M  END
> <DATABASE_ID>
NP0022115

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(Cl)C([H])=C(Cl)C([H])=C1C([H])([H])C1=C(C(Cl)=C(Cl)N1[H])[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H6Cl4N2O3/c12-5-1-4(10(18)6(13)3-5)2-7-9(17(19)20)8(14)11(15)16-7/h1,3,16,18H,2H2

> <INCHI_KEY>
ZIOBWQJYKHDNKP-UHFFFAOYSA-N

> <FORMULA>
C11H6Cl4N2O3

> <MOLECULAR_WEIGHT>
355.98

> <EXACT_MASS>
353.9132529

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
30.480987255133616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
({4,5-dichloro-2-[(3,5-dichloro-2-hydroxyphenyl)methyl]-1H-pyrrol-3-yl}nitro)-lambda1-oxidanyl

> <ALOGPS_LOGP>
5.15

> <JCHEM_LOGP>
4.676625848

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.222679735994594

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.404312727551609

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057200656368756

> <JCHEM_POLAR_SURFACE_AREA>
79.16

> <JCHEM_REFRACTIVITY>
78.10719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{4,5-dichloro-2-[(3,5-dichloro-2-hydroxyphenyl)methyl]-1H-pyrrol-3-ylnitro}-lambda1-oxidanyl

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -1.385  -1.847   1.625  0.00  0.00           O+0
HETATM    2  N   UNK     0      -1.898  -1.871   0.490  0.00  0.00           N+1
HETATM    3  O   UNK     0      -2.292  -3.091   0.012  0.00  0.00           O-1
HETATM    4  C   UNK     0      -2.067  -0.631  -0.185  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.196   0.099  -0.935  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.195  -0.122  -1.336  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.232   0.082  -0.342  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.746   1.375  -0.148  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.675   1.649   0.830  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       3.322   3.262   1.079  0.00  0.00          Cl+0
HETATM   11  C   UNK     0       3.122   0.632   1.648  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.634  -0.653   1.480  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       3.200  -1.949   2.513  0.00  0.00          Cl+0
HETATM   14  C   UNK     0       1.686  -0.910   0.474  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.284  -2.228   0.394  0.00  0.00           O+0
HETATM   16  N   UNK     0      -1.852   1.224  -1.371  0.00  0.00           N+0
HETATM   17  C   UNK     0      -3.101   1.188  -0.901  0.00  0.00           C+0
HETATM   18 Cl   UNK     0      -4.322   2.427  -1.199  0.00  0.00          Cl+0
HETATM   19  C   UNK     0      -3.299   0.055  -0.153  0.00  0.00           C+0
HETATM   20 Cl   UNK     0      -4.735  -0.474   0.677  0.00  0.00          Cl+0
HETATM   21  H   UNK     0       0.211  -1.186  -1.752  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.413   0.487  -2.265  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.404   2.180  -0.786  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.861   0.799   2.445  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.633  -2.500  -0.317  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.470   2.006  -1.975  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   19                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7   21   22                                             
CONECT    7    6    8   14                                                  
CONECT    8    7    9   23                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   24                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15    7                                                  
CONECT   15   14   25                                                       
CONECT   16    5   17   26                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20    4                                                  
CONECT   20   19                                                            
CONECT   21    6                                                            
CONECT   22    6                                                            
CONECT   23    8                                                            
CONECT   24   11                                                            
CONECT   25   15                                                            
CONECT   26   16                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₁H₆Cl₄N₂O₃

Average Mass

355.9800 Da

Monoisotopic Mass

353.91325 Da

IUPAC Name

({4,5-dichloro-2-[(3,5-dichloro-2-hydroxyphenyl)methyl]-1H-pyrrol-3-yl}nitro)-lambda1-oxidanyl

Traditional Name

{4,5-dichloro-2-[(3,5-dichloro-2-hydroxyphenyl)methyl]-1H-pyrrol-3-ylnitro}-lambda1-oxidanyl

CAS Registry Number

Not Available

SMILES

OC1=C(Cl)C=C(Cl)C=C1CC1=C(C(Cl)=C(Cl)N1)[N+]([O-])=O

InChI Identifier

InChI=1S/C11H6Cl4N2O3/c12-5-1-4(10(18)6(13)3-5)2-7-9(17(19)20)8(14)11(15)16-7/h1,3,16,18H,2H2

InChI Key

ZIOBWQJYKHDNKP-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
Streptomyces sp.	NPAtlas	7309630

Species Where Detected

Species Name	Source	Reference
Streptomyces SF-2080	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

Alternative Parents

Substituents

Nitroaromatic compound
1,3-dichlorobenzene
4-halophenol
2-halophenol
2-chlorophenol
4-chlorophenol
Phenol
Aryl chloride
Aryl halide
Substituted pyrrole
Heteroaromatic compound
Pyrrole
C-nitro compound
Organic nitro compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organohalogen compound
Organic oxygen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	5.15	ALOGPS
logP	4.68	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	7.4	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.16 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.11 m³·mol⁻¹	ChemAxon
Polarizability	30.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA020405

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018377

Chemspider ID

117580

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133274

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ezaki N, Shomura T, Koyama M, Niwa T, Kojima M, Inouye S, Ito T, Niida T: New chlorinated nitro-pyrrole antibiotics, pyrrolomycin A and B (SF-2080 A and B). J Antibiot (Tokyo). 1981 Oct;34(10):1363-5. doi: 10.7164/antibiotics.34.1363. [PubMed:7309630 ]

Showing NP-Card for Pyrrolomycin B (NP0022115)

MOL for NP0022115 (Pyrrolomycin B)

3D MOL for NP0022115 (Pyrrolomycin B)

3D SDF for NP0022115 (Pyrrolomycin B)

3D-SDF for NP0022115 (Pyrrolomycin B)

PDB for NP0022115 (Pyrrolomycin B)

3D PDB for NP0022115 (Pyrrolomycin B)

SMILES for NP0022115 (Pyrrolomycin B)

INCHI for NP0022115 (Pyrrolomycin B)

Structure for NP0022115 (Pyrrolomycin B)

3D Structure for NP0022115 (Pyrrolomycin B)