NP-MRD: Showing NP-Card for Pyrrolomycin A (NP0022114)

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Record Information

Version

1.0

Created at

2021-01-06 07:20:17 UTC

Updated at

2021-07-15 17:38:10 UTC

NP-MRD ID

NP0022114

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyrrolomycin A

Provided By

NPAtlas

Description

Pyrrolomycin A, also known as SF-2080 a, belongs to the class of organic compounds known as nitroaromatic compounds. These are c-nitro compounds where the nitro group is C-substituted with an aromatic group. Pyrrolomycin A is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Pyrrolomycin A is found in Streptomyces sp. It was first documented in 1981 (PMID: 7309630). Based on a literature review a small amount of articles have been published on pyrrolomycin A (PMID: 17158935) (PMID: 26798098) (PMID: 7333969) (PMID: 34383398).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

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      -2.904   0.022  -0.503  0.00  0.00           O+0
HETATM    2  N   UNK     0      -1.994   0.562   0.146  0.00  0.00           N+1
HETATM    3  O   UNK     0      -2.316   1.600   0.974  0.00  0.00           O-1
HETATM    4  C   UNK     0      -0.656   0.108   0.025  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.201  -1.161  -0.309  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.159  -1.171  -0.313  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.610   0.052   0.008  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       3.281   0.589   0.147  0.00  0.00          Cl+0
HETATM    9  C   UNK     0       0.520   0.842   0.217  0.00  0.00           C+0
HETATM   10 Cl   UNK     0       0.552   2.541   0.663  0.00  0.00          Cl+0
HETATM   11  H   UNK     0      -0.838  -2.005  -0.530  0.00  0.00           H+0
HETATM   12  H   UNK     0       1.785  -1.980  -0.526  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10    4                                                  
CONECT   10    9                                                            
CONECT   11    5                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2,3-Dichloro-4-nitropyrrole	ChEBI
Antibiotic SF 2080a	ChEBI
SF-2080 a	ChEBI
SF-2080a	ChEBI

Chemical Formula

C₄H₂Cl₂N₂O₂

Average Mass

180.9700 Da

Monoisotopic Mass

179.94933 Da

IUPAC Name

[(4,5-dichloro-1H-pyrrol-3-yl)nitro]-lambda1-oxidanyl

Traditional Name

(4,5-dichloro-1H-pyrrol-3-ylnitro)-lambda1-oxidanyl

CAS Registry Number

Not Available

SMILES

[O-][N+](=O)C1=CNC(Cl)=C1Cl

InChI Identifier

InChI=1S/C4H2Cl2N2O2/c5-3-2(8(9)10)1-7-4(3)6/h1,7H

InChI Key

CDHAYBUDIPNGGJ-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 nitroaromatic compounds. These are c-nitro compounds where the nitro group is C-substituted with an aromatic group.

Kingdom

Organic compounds

Super Class

Organic 1,3-dipolar compounds

Class

Allyl-type 1,3-dipolar organic compounds

Sub Class

Organic nitro compounds

Direct Parent

Nitroaromatic compounds

Alternative Parents

Substituents

Nitroaromatic compound
Aryl chloride
Aryl halide
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Organic oxoazanium
Propargyl-type 1,3-dipolar organic compound
Organoheterocyclic compound
Azacycle
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organochloride
Organic nitrogen compound
Organic oxygen compound
Organohalogen compound
Hydrocarbon derivative
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	2.33	ALOGPS
logP	1.92	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	11.15	ChemAxon
pKa (Strongest Basic)	-8.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	58.93 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.75 m³·mol⁻¹	ChemAxon
Polarizability	14.14 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA020404

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018376

Chemspider ID

117581

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

133275

PDB ID

Not Available

ChEBI ID

156550

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 ]
Zhang X, Parry RJ: Cloning and characterization of the pyrrolomycin biosynthetic gene clusters from Actinosporangium vitaminophilum ATCC 31673 and Streptomyces sp. strain UC 11065. Antimicrob Agents Chemother. 2007 Mar;51(3):946-57. doi: 10.1128/AAC.01214-06. Epub 2006 Dec 11. [PubMed:17158935 ]
Mahan KM, Klingeman DM, Hettich RL, Parry RJ, Graham DE: Draft Genome Sequence of Streptomyces vitaminophilus ATCC 31673, a Producer of Pyrrolomycin Antibiotics, Some of Which Contain a Nitro Group. Genome Announc. 2016 Jan 21;4(1). pii: 4/1/e01582-15. doi: 10.1128/genomeA.01582-15. [PubMed:26798098 ]
Koyama M, Kodama Y, Tsuruoka T, Ezaki N, Niwa T, Inouye S: Structure and synthesis of pyrrolomycin A, a chlorinated nitro-pyrrole antibiotic. J Antibiot (Tokyo). 1981 Dec;34(12):1569-76. doi: 10.7164/antibiotics.34.1569. [PubMed:7333969 ]
Mitchell PM: The cost-effectiveness of what in health and care?. 2021 Feb. [PubMed:34383398 ]

Showing NP-Card for Pyrrolomycin A (NP0022114)

MOL for NP0022114 (Pyrrolomycin A)

3D MOL for NP0022114 (Pyrrolomycin A)

3D SDF for NP0022114 (Pyrrolomycin A)

3D-SDF for NP0022114 (Pyrrolomycin A)

PDB for NP0022114 (Pyrrolomycin A)

3D PDB for NP0022114 (Pyrrolomycin A)

SMILES for NP0022114 (Pyrrolomycin A)

INCHI for NP0022114 (Pyrrolomycin A)

Structure for NP0022114 (Pyrrolomycin A)

3D Structure for NP0022114 (Pyrrolomycin A)