Showing NP-Card for Aureothricin (NP0062212)

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Record Information
Version2.0
Created at2022-04-28 06:52:36 UTC
Updated at2022-04-28 06:52:36 UTC
NP-MRD IDNP0062212
Secondary Accession NumbersNone
Natural Product Identification
Common NameAureothricin
DescriptionAureothricin 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. Aureothricin 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. Aureothricin is found in Saccharothrix algeriensis, Streptomyces kasugaensis, Streptomyces sp. and Streptomyces thioluteus. Aureothricin was first documented in 2013 (PMID: 24141227). Based on a literature review a small amount of articles have been published on aureothricin (PMID: 27018252) (PMID: 24835149) (PMID: 27382782) (PMID: 24323287).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0062212 (Aureothricin)

  Mrv1652304282208522D          

 15 16  0  0  0  0            999 V2000
   -0.4849   -0.6674    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    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
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 N   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
    2.8792   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1832   -1.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -3.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931   -3.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242    0.7846    0.0000 C   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  2  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 15  1  0  0  0  0
M  END
Download

3D MOL for NP0062212 (Aureothricin)

     RDKit          3D

 25 26  0  0  0  0  0  0  0  0999 V2000
    4.5208   -0.1960   -0.4551 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4339    0.8134   -0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0644    0.1858   -0.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0464   -1.0491   -0.2815 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9441    1.0065   -0.0230 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3796    0.5600    0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9129   -0.7154    0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064   -2.3177   -0.1501 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1270   -3.2654   -0.0461 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0450   -1.8409    0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3405   -0.6691    0.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6146    0.6733    0.2932 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9502    1.2468    0.4638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4878    1.3933    0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4139    2.6492    0.3249 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7791   -0.3037   -1.5500 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2549   -1.1997   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4652    0.0935    0.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3995    1.5175   -1.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5544    1.3644    0.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1311    2.0744    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1649   -1.9207    0.2491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6774    0.4733    0.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2515    1.6688   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9224    2.0931    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 14  6  1  0
 11  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  5 21  1  0
 10 22  1  0
 13 23  1  0
 13 24  1  0
 13 25  1  0
M  END
Download

3D SDF for NP0062212 (Aureothricin)

  Mrv1652304282208522D          

 15 16  0  0  0  0            999 V2000
   -0.4849   -0.6674    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    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
   -0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 N   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
    2.8792   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -2.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1832   -1.6779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8861   -3.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931   -3.2472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242    0.7846    0.0000 C   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  2  0  0  0  0
  1  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  3  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0062212

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10N2O2S2/c1-3-6(12)10-7-8-5(4-14-15-8)11(2)9(7)13/h4H,3H2,1-2H3,(H,10,12)

> <INCHI_KEY>
UGZYFXMSMFMTSM-UHFFFAOYSA-N

> <FORMULA>
C9H10N2O2S2

> <MOLECULAR_WEIGHT>
242.31

> <EXACT_MASS>
242.018369918

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
23.949928377104456

> <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}propanamide

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
0.17304923166666664

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.470644167339227

> <JCHEM_PKA_STRONGEST_BASIC>
-4.620151721174477

> <JCHEM_POLAR_SURFACE_AREA>
49.410000000000004

> <JCHEM_REFRACTIVITY>
64.9734

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aureothricin

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0062212 (Aureothricin)

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PDB for NP0062212 (Aureothricin)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  S   UNK     0      -0.905  -1.246   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      -0.000  -2.492   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.929   0.000   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.374  -1.246   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.405  -3.956   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.911  -4.277   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.942  -3.132   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.387  -5.741   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.894  -6.061   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.405   1.465   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7   15                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15    6                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

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3D PDB for NP0062212 (Aureothricin)
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SMILES for NP0062212 (Aureothricin)
CCC(=O)NC1=C2SSC=C2N(C)C1=O
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INCHI for NP0062212 (Aureothricin)
InChI=1S/C9H10N2O2S2/c1-3-6(12)10-7-8-5(4-14-15-8)11(2)9(7)13/h4H,3H2,1-2H3,(H,10,12)
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Synonyms
ValueSource
4-Methyl-6-propionamido-1,2-dithiolo[4,3-b]pyrrol-5(4H)-oneChEBI
N-(4,5-Dihydro-4-methyl-5-oxo-1,2-dithiolo[4,3-b]pyrrol-6-yl)propionamideChEBI
N-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6- yl}propanamideChEBI
Propanoyl-pyrrothineChEBI
PropionopyrrothineChEBI
Chemical FormulaC9H10N2O2S2
Average Mass242.3100 Da
Monoisotopic Mass242.01837 Da
IUPAC NameN-{4-methyl-5-oxo-4H,5H-[1,2]dithiolo[4,3-b]pyrrol-6-yl}propanamide
Traditional Nameaureothricin
CAS Registry NumberNot Available
SMILES
CCC(=O)NC1=C2SSC=C2N(C)C1=O
InChI Identifier
InChI=1S/C9H10N2O2S2/c1-3-6(12)10-7-8-5(4-14-15-8)11(2)9(7)13/h4H,3H2,1-2H3,(H,10,12)
InChI KeyUGZYFXMSMFMTSM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Saccharothrix algeriensisLOTUS Database
Streptomyces kasugaensisLOTUS Database
Streptomyces sp.Bacteria
Streptomyces thioluteusLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassN-arylamides  
Direct ParentN-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
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.35ALOGPS
logP0.17ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)12.47ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.41 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.97 m³·mol⁻¹ChemAxon
Polarizability23.95 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00018653  
Chemspider ID61737  
KEGG Compound IDNot Available
BioCyc IDCPD-17938  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68460  
PDB IDNot Available
ChEBI ID156452  
Good Scents IDNot Available
References
General References
  1. Zhai Y, Bai S, Liu J, Yang L, Han L, Huang X, He J: Identification of an unusual type II thioesterase in the dithiolopyrrolone antibiotics biosynthetic pathway. Biochem Biophys Res Commun. 2016 Apr 22;473(1):329-335. doi: 10.1016/j.bbrc.2016.03.105. Epub 2016 Mar 24. [PubMed:27018252  ] 
  2. Li B, Wever WJ, Walsh CT, Bowers AA: Dithiolopyrrolones: biosynthesis, synthesis, and activity of a unique class of disulfide-containing antibiotics. Nat Prod Rep. 2014 Jul;31(7):905-23. doi: 10.1039/c3np70106a. [PubMed:24835149  ] 
  3. Qin Z, Huang S, Yu Y, Deng H: Dithiolopyrrolone natural products: isolation, synthesis and biosynthesis. Mar Drugs. 2013 Oct 17;11(10):3970-97. doi: 10.3390/md11103970. [PubMed:24141227  ] 
  4. Huang S, Yu Y: [Biosynthesis and metabolic engineering of dithiolopyrrolone - A review]. Wei Sheng Wu Xue Bao. 2016 Mar 4;56(3):383-96. [PubMed:27382782  ] 
  5. Liras P: Holomycin, a dithiolopyrrolone compound produced by Streptomyces clavuligerus. Appl Microbiol Biotechnol. 2014 Feb;98(3):1023-30. doi: 10.1007/s00253-013-5410-z. Epub 2013 Dec 10. [PubMed:24323287  ]