NP-MRD: Showing NP-Card for n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid (NP0290367)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 21:01:22 UTC

Updated at

2022-09-09 21:01:22 UTC

NP-MRD ID

NP0290367

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid

Description

Formylpyrrothine belongs to the class of organic compounds known as n-arylamides. These are organic compounds that contain a carboxamide group that is N-linked to a aryl group. They have the generic structure RC(=O)N(R')H, R = organyl group and R'= aryl group. n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid is found in Saccharothrix algeriensis. n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid was first documented in 2010 (PMID: 20507156). Based on a literature review very few articles have been published on formylpyrrothine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092223012D          

 13 14  0  0  0  0            999 V2000
    1.0146    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -1.8785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473   -2.6631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0404   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  4  0  0  0
  8 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0290367

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)C(N=CO)=C2SSC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C7H6N2O2S2/c1-9-4-2-12-13-6(4)5(7(9)11)8-3-10/h2-3H,1H3,(H,8,10)

> <INCHI_KEY>
JSPVCJSCSHLERJ-UHFFFAOYSA-N

> <FORMULA>
C7H6N2O2S2

> <MOLECULAR_WEIGHT>
214.26

> <EXACT_MASS>
213.987069789

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
20.082508762086526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid

> <JCHEM_LOGP>
0.24341880366666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7126296878432723

> <JCHEM_PKA_STRONGEST_BASIC>
0.4572107474453307

> <JCHEM_POLAR_SURFACE_AREA>
52.9

> <JCHEM_REFRACTIVITY>
56.37770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       1.894   2.235   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.370   0.770   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0       6.204  -0.476   0.000  0.00  0.00           S+0
HETATM    6  S   UNK     0       5.299  -1.722   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.894  -3.186   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.388  -3.507   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.088  -4.971   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.075  -0.476   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    3    8                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    8    2   13                                                  
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₇H₆N₂O₂S₂

Average Mass

214.2600 Da

Monoisotopic Mass

213.98707 Da

IUPAC Name

N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid

Traditional Name

N-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid

CAS Registry Number

Not Available

SMILES

CN1C(=O)C(N=CO)=C2SSC=C12

InChI Identifier

InChI=1S/C7H6N2O2S2/c1-9-4-2-12-13-6(4)5(7(9)11)8-3-10/h2-3H,1H3,(H,8,10)

InChI Key

JSPVCJSCSHLERJ-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Saccharothrix algeriensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-arylamides. These are organic compounds that contain a carboxamide group that is N-linked to a aryl group. They have the generic structure RC(=O)N(R')H, R = organyl group and R'= aryl group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

N-arylamides

Direct Parent

N-arylamides

Alternative Parents

Substituents

N-arylamide
N-methylpyrrole
Substituted pyrrole
Pyrrole
Heteroaromatic compound
1,2-dithiole
Dithiole
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.24	ChemAxon
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	0.46	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	56.38 m³·mol⁻¹	ChemAxon
Polarizability	20.08 Å³	ChemAxon
Number of Rings	2	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

25061331

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46848162

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Merrouche R, Bouras N, Coppel Y, Mathieu F, Monje MC, Sabaou N, Lebrihi A: Dithiolopyrrolone antibiotic formation induced by adding valeric acid to the culture broth of Saccharothrix algeriensis. J Nat Prod. 2010 Jun 25;73(6):1164-6. doi: 10.1021/np900808u. [PubMed:20507156 ]
LOTUS database [Link]

Showing NP-Card for n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid (NP0290367)

MOL for NP0290367 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid)

3D MOL for NP0290367 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid)

3D SDF for NP0290367 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid)

3D-SDF for NP0290367 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid)

PDB for NP0290367 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid)

3D PDB for NP0290367 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid)

SMILES for NP0290367 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid)

INCHI for NP0290367 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid)

Structure for NP0290367 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid)

3D Structure for NP0290367 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}carboximidic acid)