NP-MRD: Showing NP-Card for Pyrrolomycin F3 (NP0021933)

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Record Information

Version

2.0

Created at

2021-01-06 07:10:38 UTC

Updated at

2021-07-15 17:37:41 UTC

NP-MRD ID

NP0021933

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyrrolomycin F3

Provided By

NPAtlas

Description

Pyrrolomycin F3 is found in Streptomyces. Based on a literature review very few articles have been published on 4-bromo-2-(3-bromo-4,5-dichloro-1H-pyrrole-2-carbonyl)phenol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105193D          

 23 24  0  0  0  0            999 V2000
    0.2806   -1.5404   -1.9003 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3104   -0.7396   -0.9280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9109   -0.1739   -0.3813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372    0.7061    0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9832    1.2442    1.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8762    2.4463    2.6914 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2098    0.9118    0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2649    0.0317   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1258   -0.5203   -0.9478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966   -1.4004   -2.0132 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6156   -0.4055   -0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792    0.5426   -0.7935 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5841    0.5560   -0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9901    1.5931   -0.1945 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4740   -0.4285    0.9094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6299   -0.8613    2.1532 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.2334   -1.0203    0.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5734   -2.4592    1.7583 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.0910    0.9886    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1035    1.3397    1.0743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2133   -0.2452   -0.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8991   -1.7370   -2.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2586    1.1715   -1.6082 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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  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
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9  3  1  0  0  0  0
 17 11  2  0  0  0  0
  4 19  1  0  0  0  0
  7 20  1  0  0  0  0
  8 21  1  0  0  0  0
 10 22  1  0  0  0  0
 12 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021933

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H5Br2Cl2NO2/c12-4-1-2-6(17)5(3-4)10(18)9-7(13)8(14)11(15)16-9/h1-3,16-17H

> <INCHI_KEY>
ICQSKHARNVQSEP-UHFFFAOYSA-N

> <FORMULA>
C11H5Br2Cl2NO2

> <MOLECULAR_WEIGHT>
413.87

> <EXACT_MASS>
410.80641

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
30.478657318333717

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-bromo-2-(3-bromo-4,5-dichloro-1H-pyrrole-2-carbonyl)phenol

> <ALOGPS_LOGP>
4.77

> <JCHEM_LOGP>
5.239524027

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.609260672416314

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.62711364117358

> <JCHEM_PKA_STRONGEST_BASIC>
-7.526567066540038

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
78.107

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-bromo-2-(3-bromo-4,5-dichloro-1H-pyrrole-2-carbonyl)phenol

> <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       0.281  -1.540  -1.900  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.310  -0.740  -0.928  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.911  -0.174  -0.381  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.837   0.706   0.697  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.983   1.244   1.213  0.00  0.00           C+0
HETATM    6 Br   UNK     0      -1.876   2.446   2.691  0.00  0.00          Br+0
HETATM    7  C   UNK     0      -3.210   0.912   0.662  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.265   0.032  -0.414  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.126  -0.520  -0.948  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.097  -1.400  -2.013  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.616  -0.406  -0.380  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.479   0.543  -0.794  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.584   0.556  -0.055  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       4.990   1.593  -0.195  0.00  0.00          Cl+0
HETATM   15  C   UNK     0       3.474  -0.429   0.909  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       4.630  -0.861   2.153  0.00  0.00          Cl+0
HETATM   17  C   UNK     0       2.233  -1.020   0.690  0.00  0.00           C+0
HETATM   18 Br   UNK     0       1.573  -2.459   1.758  0.00  0.00          Br+0
HETATM   19  H   UNK     0       0.091   0.989   1.151  0.00  0.00           H+0
HETATM   20  H   UNK     0      -4.104   1.340   1.074  0.00  0.00           H+0
HETATM   21  H   UNK     0      -4.213  -0.245  -0.866  0.00  0.00           H+0
HETATM   22  H   UNK     0      -2.899  -1.737  -2.517  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.259   1.172  -1.608  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   20                                                  
CONECT    8    7    9   21                                                  
CONECT    9    8   10    3                                                  
CONECT   10    9   22                                                       
CONECT   11    2   12   17                                                  
CONECT   12   11   13   23                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   11                                                  
CONECT   18   17                                                            
CONECT   19    4                                                            
CONECT   20    7                                                            
CONECT   21    8                                                            
CONECT   22   10                                                            
CONECT   23   12                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Pyrrolomycin F2b	MeSH
Pyrrolomycin F2a	MeSH
Pyrrolomycin F	MeSH
Pyrrolomycin F1	MeSH

Chemical Formula

C₁₁H₅Br₂Cl₂NO₂

Average Mass

413.8700 Da

Monoisotopic Mass

410.80641 Da

IUPAC Name

4-bromo-2-(3-bromo-4,5-dichloro-1H-pyrrole-2-carbonyl)phenol

Traditional Name

4-bromo-2-(3-bromo-4,5-dichloro-1H-pyrrole-2-carbonyl)phenol

CAS Registry Number

Not Available

SMILES

OC1=C(C=C(Br)C=C1)C(=O)C1=C(Br)C(Cl)=C(Cl)N1

InChI Identifier

InChI=1S/C11H5Br2Cl2NO2/c12-4-1-2-6(17)5(3-4)10(18)9-7(13)8(14)11(15)16-9/h1-3,16-17H

InChI Key

ICQSKHARNVQSEP-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	NPAtlas	6686223

Species Where Detected

Species Name	Source	Reference
Actinosporangium vitaminophilum sp. nov.	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Aryl-phenylketones

Alternative Parents

Substituents

Aryl-phenylketone
Benzoyl
4-halophenol
4-bromophenol
Bromobenzene
Halobenzene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Substituted pyrrole
Aryl halide
Monocyclic benzene moiety
Aryl bromide
Aryl chloride
Vinylogous acid
Vinylogous halide
Pyrrole
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organohalogen compound
Organic nitrogen compound
Organobromide
Organochloride
Organonitrogen compound
Organic oxide
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	4.77	ALOGPS
logP	5.24	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	6.63	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.11 m³·mol⁻¹	ChemAxon
Polarizability	30.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA020930

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018544

Chemspider ID

76758509

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102115512

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Pyrrolomycin F3 (NP0021933)

MOL for NP0021933 (Pyrrolomycin F3)

3D MOL for NP0021933 (Pyrrolomycin F3)

3D SDF for NP0021933 (Pyrrolomycin F3)

3D-SDF for NP0021933 (Pyrrolomycin F3)

PDB for NP0021933 (Pyrrolomycin F3)

3D PDB for NP0021933 (Pyrrolomycin F3)

SMILES for NP0021933 (Pyrrolomycin F3)

INCHI for NP0021933 (Pyrrolomycin F3)

Structure for NP0021933 (Pyrrolomycin F3)

3D Structure for NP0021933 (Pyrrolomycin F3)