NP-MRD: Showing NP-Card for Pyrrolomycin D (NP0021927)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-01-06 07:10:22 UTC

Updated at

2021-07-15 17:37:40 UTC

NP-MRD ID

NP0021927

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyrrolomycin D

Provided By

NPAtlas

Description

Pyrrolomycin D is found in Streptomyces. Pyrrolomycin D was first documented in 1983 (PMID: 6685720). Based on a literature review very few articles have been published on 2,4-dichloro-6-(3,4,5-trichloro-1H-pyrrole-2-carbonyl)phenol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105193D          

 23 24  0  0  0  0            999 V2000
   -0.3633    1.7048   -1.6729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4023    0.7465   -0.8378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8157    0.3893   -0.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8639   -0.5353    0.8749 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0681   -0.8177    1.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0576   -2.0179    2.8206 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2445   -0.2041    1.1832 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2137    0.7214    0.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7236    1.5210   -0.2793 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0315    1.0023   -0.4705 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9969    1.9372   -1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6446    0.0360   -0.5914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8731   -1.2878   -0.4597 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1804   -1.5296   -0.2192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8668   -3.1193    0.0104 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8508   -0.3288   -0.1892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5820   -0.0787    0.0919 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.9090    0.6336   -0.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2015    2.3576   -0.4932 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0166   -1.0493    1.2078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1753   -0.4368    1.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8379    2.3938   -1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1381   -2.0382   -0.5455 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  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10  3  1  0  0  0  0
 18 12  2  0  0  0  0
  4 20  1  0  0  0  0
  7 21  1  0  0  0  0
 11 22  1  0  0  0  0
 13 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021927

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H4Cl5NO2/c12-3-1-4(9(18)5(13)2-3)10(19)8-6(14)7(15)11(16)17-8/h1-2,17-18H

> <INCHI_KEY>
IJODRMYZNYTFTC-UHFFFAOYSA-N

> <FORMULA>
C11H4Cl5NO2

> <MOLECULAR_WEIGHT>
359.41

> <EXACT_MASS>
356.8684669

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
30.865787952809058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4-dichloro-6-(3,4,5-trichloro-1H-pyrrole-2-carbonyl)phenol

> <ALOGPS_LOGP>
5.30

> <JCHEM_LOGP>
5.5141528053333335

> <ALOGPS_LOGS>
-4.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.94448907894697

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.083760544499333

> <JCHEM_PKA_STRONGEST_BASIC>
-8.060832293955482

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
77.27579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4-dichloro-6-(3,4,5-trichloro-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      -0.363   1.705  -1.673  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.402   0.747  -0.838  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.816   0.389  -0.145  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.864  -0.535   0.875  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.068  -0.818   1.521  0.00  0.00           C+0
HETATM    6 Cl   UNK     0       2.058  -2.018   2.821  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       3.244  -0.204   1.183  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.214   0.721   0.167  0.00  0.00           C+0
HETATM    9 Cl   UNK     0       4.724   1.521  -0.279  0.00  0.00          Cl+0
HETATM   10  C   UNK     0       2.031   1.002  -0.471  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.997   1.937  -1.496  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.645   0.036  -0.591  0.00  0.00           C+0
HETATM   13  N   UNK     0      -1.873  -1.288  -0.460  0.00  0.00           N+0
HETATM   14  C   UNK     0      -3.180  -1.530  -0.219  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      -3.867  -3.119   0.010  0.00  0.00          Cl+0
HETATM   16  C   UNK     0      -3.851  -0.329  -0.189  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      -5.582  -0.079   0.092  0.00  0.00          Cl+0
HETATM   18  C   UNK     0      -2.909   0.634  -0.418  0.00  0.00           C+0
HETATM   19 Cl   UNK     0      -3.201   2.358  -0.493  0.00  0.00          Cl+0
HETATM   20  H   UNK     0      -0.017  -1.049   1.208  0.00  0.00           H+0
HETATM   21  H   UNK     0       4.175  -0.437   1.701  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.838   2.394  -1.759  0.00  0.00           H+0
HETATM   23  H   UNK     0      -1.138  -2.038  -0.546  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   21                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11    3                                                  
CONECT   11   10   22                                                       
CONECT   12    2   13   18                                                  
CONECT   13   12   14   23                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   12                                                  
CONECT   19   18                                                            
CONECT   20    4                                                            
CONECT   21    7                                                            
CONECT   22   11                                                            
CONECT   23   13                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₁H₄Cl₅NO₂

Average Mass

359.4100 Da

Monoisotopic Mass

356.86847 Da

IUPAC Name

2,4-dichloro-6-(3,4,5-trichloro-1H-pyrrole-2-carbonyl)phenol

Traditional Name

2,4-dichloro-6-(3,4,5-trichloro-1H-pyrrole-2-carbonyl)phenol

CAS Registry Number

Not Available

SMILES

OC1=C(Cl)C=C(Cl)C=C1C(=O)C1=C(Cl)C(Cl)=C(Cl)N1

InChI Identifier

InChI=1S/C11H4Cl5NO2/c12-3-1-4(9(18)5(13)2-3)10(19)8-6(14)7(15)11(16)17-8/h1-2,17-18H

InChI Key

IJODRMYZNYTFTC-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	6685720

Species Where Detected

Species Name	Source	Reference
Actinosporangium vitaminophilum SF-2080	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
1,3-dichlorobenzene
4-halophenol
2-halophenol
2-chlorophenol
4-chlorophenol
Chlorobenzene
Halobenzene
Phenol
Benzenoid
Substituted pyrrole
Aryl halide
Monocyclic benzene moiety
Aryl chloride
Pyrrole
Vinylogous acid
Vinylogous halide
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organohalogen compound
Organochloride
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	5.3	ALOGPS
logP	5.51	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	5.08	ChemAxon
pKa (Strongest Basic)	-8.1	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	77.28 m³·mol⁻¹	ChemAxon
Polarizability	30.87 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

NPA020409

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018532

Chemspider ID

117988

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133780

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ezaki N, Koyama M, Shomura T, Tsuruoka T, Inouye S: Pyrrolomycins C, D and E, new members of pyrrolomycins. J Antibiot (Tokyo). 1983 Oct;36(10):1263-7. doi: 10.7164/antibiotics.36.1263. [PubMed:6685720 ]

Showing NP-Card for Pyrrolomycin D (NP0021927)

MOL for NP0021927 (Pyrrolomycin D)

3D MOL for NP0021927 (Pyrrolomycin D)

3D SDF for NP0021927 (Pyrrolomycin D)

3D-SDF for NP0021927 (Pyrrolomycin D)

PDB for NP0021927 (Pyrrolomycin D)

3D PDB for NP0021927 (Pyrrolomycin D)

SMILES for NP0021927 (Pyrrolomycin D)

INCHI for NP0021927 (Pyrrolomycin D)

Structure for NP0021927 (Pyrrolomycin D)

3D Structure for NP0021927 (Pyrrolomycin D)