NP-MRD: Showing NP-Card for Pyrrolomycin G (NP0005720)

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Record Information

Version

2.0

Created at

2020-12-09 02:53:30 UTC

Updated at

2021-07-15 16:52:48 UTC

NP-MRD ID

NP0005720

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyrrolomycin G

Provided By

NPAtlas

Description

Pyrrolomycin G 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 G is found in Streptomyces fumanus. Pyrrolomycin G was first documented in 2005 (PMID: 15730262). Based on a literature review very few articles have been published on pyrrolomycin G.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118223D          

 27 28  0  0  0  0            999 V2000
   -0.4354    2.3415   -1.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092    2.1488   -0.4056 N   0  3  0  0  0  4  0  0  0  0  0  0
   -1.9602    3.2059    0.2585 O   0  5  0  0  0  1  0  0  0  0  0  0
   -1.9433    0.8655   -0.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606   -0.1941    0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2332   -0.1889    1.3212 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2676   -1.3497    2.1220 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0151   -0.0342    0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925    1.1015    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9787    1.2369    0.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9252    2.6904    0.4348 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4283    0.3011   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6619   -0.8232   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2347   -2.0124   -2.1378 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4535   -0.9788   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285   -2.1263   -0.5636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2925   -1.2127    0.3058 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3045   -0.8433   -0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6545   -1.8471   -1.0366 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1299    0.4663   -0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1264    1.4521   -1.9506 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3242    0.6459    2.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3683   -2.1744    1.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4446    1.8644    1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3791    0.4245   -1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0887   -2.7911   -1.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2207   -2.1686    0.7188 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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20  4  1  0  0  0  0
 15  8  1  0  0  0  0
  6 22  1  1  0  0  0
  7 23  1  0  0  0  0
  9 24  1  0  0  0  0
 12 25  1  0  0  0  0
 16 26  1  0  0  0  0
 17 27  1  0  0  0  0
M  CHG  2   2   1   3  -1
M  END


  Mrv1652306242118223D          

 27 28  0  0  0  0            999 V2000
   -0.4354    2.3415   -1.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4092    2.1488   -0.4056 N   0  3  0  0  0  4  0  0  0  0  0  0
   -1.9602    3.2059    0.2585 O   0  5  0  0  0  1  0  0  0  0  0  0
   -1.9433    0.8655   -0.2623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606   -0.1941    0.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2332   -0.1889    1.3212 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2676   -1.3497    2.1220 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0151   -0.0342    0.5909 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925    1.1015    0.8107 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9787    1.2369    0.1221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9252    2.6904    0.4348 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4283    0.3011   -0.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6619   -0.8232   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2347   -2.0124   -2.1378 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4535   -0.9788   -0.3005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7285   -2.1263   -0.5636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2925   -1.2127    0.3058 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3045   -0.8433   -0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6545   -1.8471   -1.0366 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1299    0.4663   -0.9035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1264    1.4521   -1.9506 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3242    0.6459    2.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3683   -2.1744    1.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4446    1.8644    1.5268 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3791    0.4245   -1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0887   -2.7911   -1.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2207   -2.1686    0.7188 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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20  4  1  0  0  0  0
 15  8  1  0  0  0  0
  6 22  1  1  0  0  0
  7 23  1  0  0  0  0
  9 24  1  0  0  0  0
 12 25  1  0  0  0  0
 16 26  1  0  0  0  0
 17 27  1  0  0  0  0
M  CHG  2   2   1   3  -1
M  END
> <DATABASE_ID>
NP0005720

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H6Cl4N2O4/c12-3-1-4(9(18)5(13)2-3)10(19)7-8(17(20)21)6(14)11(15)16-7/h1-2,10,16,18-19H/t10-/m0/s1

> <INCHI_KEY>
WKEODUMIDZIAED-JTQLQIEISA-N

> <FORMULA>
C11H6Cl4N2O4

> <MOLECULAR_WEIGHT>
371.98

> <EXACT_MASS>
369.9081675

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
31.159405560869352

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
3.757629701

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.06447737540983

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.762107649903737

> <JCHEM_PKA_STRONGEST_BASIC>
-3.906878444446556

> <JCHEM_POLAR_SURFACE_AREA>
99.39000000000001

> <JCHEM_REFRACTIVITY>
79.3147

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{4,5-dichloro-2-[(S)-(3,5-dichloro-2-hydroxyphenyl)(hydroxy)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      -0.435   2.341  -1.147  0.00  0.00           O+0
HETATM    2  N   UNK     0      -1.409   2.149  -0.406  0.00  0.00           N+1
HETATM    3  O   UNK     0      -1.960   3.206   0.259  0.00  0.00           O-1
HETATM    4  C   UNK     0      -1.943   0.866  -0.262  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.461  -0.194   0.471  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.233  -0.189   1.321  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.268  -1.350   2.122  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.015  -0.034   0.591  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.793   1.101   0.811  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.979   1.237   0.122  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       3.925   2.690   0.435  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       3.428   0.301  -0.771  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.662  -0.823  -0.991  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       3.235  -2.012  -2.138  0.00  0.00          Cl+0
HETATM   15  C   UNK     0       1.454  -0.979  -0.301  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.729  -2.126  -0.564  0.00  0.00           O+0
HETATM   17  N   UNK     0      -2.293  -1.213   0.306  0.00  0.00           N+0
HETATM   18  C   UNK     0      -3.305  -0.843  -0.516  0.00  0.00           C+0
HETATM   19 Cl   UNK     0      -4.654  -1.847  -1.037  0.00  0.00          Cl+0
HETATM   20  C   UNK     0      -3.130   0.466  -0.904  0.00  0.00           C+0
HETATM   21 Cl   UNK     0      -4.126   1.452  -1.951  0.00  0.00          Cl+0
HETATM   22  H   UNK     0      -0.324   0.646   2.087  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.368  -2.174   1.549  0.00  0.00           H+0
HETATM   24  H   UNK     0       1.445   1.864   1.527  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.379   0.425  -1.316  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.089  -2.791  -1.227  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.221  -2.169   0.719  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   20                                                  
CONECT    5    4    6   17                                                  
CONECT    6    5    7    8   22                                             
CONECT    7    6   23                                                       
CONECT    8    6    9   15                                                  
CONECT    9    8   10   24                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   25                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16    8                                                  
CONECT   16   15   26                                                       
CONECT   17    5   18   27                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21    4                                                  
CONECT   21   20                                                            
CONECT   22    6                                                            
CONECT   23    7                                                            
CONECT   24    9                                                            
CONECT   25   12                                                            
CONECT   26   16                                                            
CONECT   27   17                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₁H₆Cl₄N₂O₄

Average Mass

371.9800 Da

Monoisotopic Mass

369.90817 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@H](C1=C(C(Cl)=C(Cl)N1)[N+]([O-])=O)C1=CC(Cl)=CC(Cl)=C1O

InChI Identifier

InChI=1S/C11H6Cl4N2O4/c12-3-1-4(9(18)5(13)2-3)10(19)7-8(17(20)21)6(14)11(15)16-7/h1-2,10,16,18-19H/t10-/m0/s1

InChI Key

WKEODUMIDZIAED-JTQLQIEISA-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 fumanus	NPAtlas	15730262

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
Secondary alcohol
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organoheterocyclic compound
Organic oxoazanium
Organic nitrogen compound
Organonitrogen compound
Organochloride
Organooxygen compound
Organohalogen compound
Alcohol
Organic salt
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic alcohol
Organic zwitterion
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	4.13	ALOGPS
logP	3.76	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.76	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.39 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.31 m³·mol⁻¹	ChemAxon
Polarizability	31.16 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

NPA009882

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00042897

Chemspider ID

9535685

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11360758

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Charan RD, Schlingmann G, Bernan VS, Feng X, Carter GT: Additional pyrrolomycins from cultures of Streptomyces fumanus. J Nat Prod. 2005 Feb;68(2):277-9. doi: 10.1021/np0496542. [PubMed:15730262 ]

Showing NP-Card for Pyrrolomycin G (NP0005720)

MOL for NP0005720 (Pyrrolomycin G)

3D MOL for NP0005720 (Pyrrolomycin G)

3D SDF for NP0005720 (Pyrrolomycin G)

3D-SDF for NP0005720 (Pyrrolomycin G)

PDB for NP0005720 (Pyrrolomycin G)

3D PDB for NP0005720 (Pyrrolomycin G)

SMILES for NP0005720 (Pyrrolomycin G)

INCHI for NP0005720 (Pyrrolomycin G)

Structure for NP0005720 (Pyrrolomycin G)

3D Structure for NP0005720 (Pyrrolomycin G)