NP-MRD: Showing NP-Card for n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}pentanimidic acid (NP0240839)

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Record Information

Version

2.0

Created at

2022-09-07 00:45:17 UTC

Updated at

2022-09-07 00:45:17 UTC

NP-MRD ID

NP0240839

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Valerylpyrrothine 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}pentanimidic acid is found in Saccharothrix algeriensis. n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}pentanimidic acid was first documented in 2010 (PMID: 20507156). Based on a literature review very few articles have been published on valerylpyrrothine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -4.8489   -0.6390   -0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0938   -0.2239    1.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6055   -0.2479    0.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3055    0.7257   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8512    0.7489   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4302    1.5943   -1.4839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0604   -0.0020    0.2107 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3255   -0.0784    0.0296 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0613   -0.3049   -1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6789   -0.5764   -2.7985 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.6722   -0.7458   -3.4055 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3375   -0.5007   -1.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4555   -0.2976   -0.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5197   -0.0690    0.5006 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7214    0.0324    1.3184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2840    0.0600    1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0575    0.2814    2.2605 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3585   -1.4677   -0.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8627   -0.9589    0.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9428    0.2481   -0.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3165   -0.8730    2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3728    0.8324    1.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0562    0.1393    1.8525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2364   -1.2525    0.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142    1.7328    0.1692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9116    0.4344   -1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8660    1.5030   -2.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4512   -0.5280   -1.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5133   -0.6866    0.9556 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5276   -0.2267    2.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1275    1.0599    1.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16  8  1  0
 13  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  6 27  1  0
 12 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
M  END


  Mrv1652309072202452D          

 17 18  0  0  0  0            999 V2000
   -1.9162    3.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1092    3.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543    2.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0473    2.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076    1.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3444    0.7556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146    1.1971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   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 S   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 C   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 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 C   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  1  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  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  9 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0240839

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC(O)=NC1=C2SSC=C2N(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O2S2/c1-3-4-5-8(14)12-9-10-7(6-16-17-10)13(2)11(9)15/h6H,3-5H2,1-2H3,(H,12,14)

> <INCHI_KEY>
AHXFDRDTTICJPB-UHFFFAOYSA-N

> <FORMULA>
C11H14N2O2S2

> <MOLECULAR_WEIGHT>
270.37

> <EXACT_MASS>
270.049670047

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
28.230982744216945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.8817906886666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.431336844591782

> <JCHEM_PKA_STRONGEST_BASIC>
0.37818030930883995

> <JCHEM_POLAR_SURFACE_AREA>
52.900000000000006

> <JCHEM_REFRACTIVITY>
74.69709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.577   6.124   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.071   5.804   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.595   4.340   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.088   4.019   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.388   2.555   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.643   1.410   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       1.894   2.235   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM   10  S   UNK     0       5.299   0.770   0.000  0.00  0.00           S+0
HETATM   11  S   UNK     0       6.204  -0.476   0.000  0.00  0.00           S+0
HETATM   12  C   UNK     0       5.299  -1.722   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.370  -1.722   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       1.894  -3.186   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.075  -0.476   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    8   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₄N₂O₂S₂

Average Mass

270.3700 Da

Monoisotopic Mass

270.04967 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CCCCC(O)=NC1=C2SSC=C2N(C)C1=O

InChI Identifier

InChI=1S/C11H14N2O2S2/c1-3-4-5-8(14)12-9-10-7(6-16-17-10)13(2)11(9)15/h6H,3-5H2,1-2H3,(H,12,14)

InChI Key

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

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

25033975

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46848160

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}pentanimidic acid (NP0240839)

MOL for NP0240839 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}pentanimidic acid)

3D MOL for NP0240839 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}pentanimidic acid)

3D SDF for NP0240839 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}pentanimidic acid)

3D-SDF for NP0240839 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}pentanimidic acid)

PDB for NP0240839 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}pentanimidic acid)

3D PDB for NP0240839 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}pentanimidic acid)

SMILES for NP0240839 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}pentanimidic acid)

INCHI for NP0240839 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}pentanimidic acid)

Structure for NP0240839 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}pentanimidic acid)

3D Structure for NP0240839 (n-{4-methyl-5-oxo-[1,2]dithiolo[4,3-b]pyrrol-6-yl}pentanimidic acid)