NP-MRD: Showing NP-Card for 2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole (NP0166899)

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Record Information

Version

2.0

Created at

2022-09-03 02:22:02 UTC

Updated at

2022-09-03 02:22:02 UTC

NP-MRD ID

NP0166899

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole

Description

AC1NEESL belongs to the class of organic compounds known as benzo-1,3-dioxanes. These are heterocyclic compounds containing a benzene ring fused to a 1,3-dioxane ring. 2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole is found in Streptomyces fumanus. AC1NEESL is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 30  0  0  0  0  0  0  0  0999 V2000
    2.8466   -2.2656    0.8746 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -1.0905    0.9082 N   0  0  0  0  0  4  0  0  0  0  0  0
    4.4042   -0.9211    1.5694 O   0  0  0  0  0  1  0  0  0  0  0  0
    2.5318    0.0305    0.3888 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3310    0.1238   -0.2716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3645   -0.9242   -0.5915 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3816   -2.0509    0.1330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3196   -2.1706    1.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1812   -1.1123    1.6029 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7790   -0.4297    0.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0451    0.0875    0.6349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9786   -0.0772    2.1051 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6018    0.7568   -0.4505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8481    0.8693   -1.5857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5208    1.7057   -2.9685 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5560    0.3332   -1.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0045   -0.3285   -0.5943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1015    1.4284   -0.6099 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261    2.1831   -0.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2966    3.9323   -0.3784 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0183    1.3360    0.4365 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5369    1.8049    1.1768 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5488   -1.2032   -1.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9439   -3.1094    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3776   -2.3264    2.1266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5913    1.1469   -0.3355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9685    0.4221   -2.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2938    1.8493   -1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  2  0
  5 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 21  4  1  0
 17  6  1  0
 17 10  1  0
 18 28  1  0
  6 23  1  6
  8 24  1  0
  8 25  1  0
 13 26  1  0
 16 27  1  0
M  CHG  2   2   1   3  -1
M  END


  Mrv1533004261517342D          

 22 24  0  0  0  0            999 V2000
   -0.1946   -1.8980    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.0231   -2.7050    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
   -0.6362   -3.2570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5315   -4.4120    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3264   -4.4120    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0964   -2.9599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 11 22  1  0  0  0  0
 15 22  1  0  0  0  0
M  CHG  2   1  -1   2   1
M  END
> <DATABASE_ID>
NP0166899

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[O-][N+](=O)C1=C(NC(Cl)=C1Cl)C1OCOC2=C(Cl)C=C(Cl)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H6Cl4N2O4/c13-4-1-5-10(6(14)2-4)21-3-22-11(5)8-9(18(19)20)7(15)12(16)17-8/h1-2,11,17H,3H2

> <INCHI_KEY>
CUPRKSFMHRXAFA-UHFFFAOYSA-N

> <FORMULA>
C12H6Cl4N2O4

> <MOLECULAR_WEIGHT>
383.99

> <EXACT_MASS>
381.9081675

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
32.200229901364715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1H-pyrrole

> <ALOGPS_LOGP>
4.54

> <JCHEM_LOGP>
4.485226259666667

> <ALOGPS_LOGS>
-4.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.052356125433581

> <JCHEM_PKA_STRONGEST_BASIC>
-4.309502937880923

> <JCHEM_POLAR_SURFACE_AREA>
77.39

> <JCHEM_REFRACTIVITY>
81.38869999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1H-pyrrole

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  O   UNK     0      -0.363  -3.543   0.000  0.00  0.00           O-1
HETATM    2  N   UNK     0      -0.043  -5.049   0.000  0.00  0.00           N+1
HETATM    3  O   UNK     0      -1.188  -6.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.421  -5.525   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.897  -6.990   0.000  0.00  0.00           C+0
HETATM    6 Cl   UNK     0       0.992  -8.236   0.000  0.00  0.00          Cl+0
HETATM    7  C   UNK     0       3.437  -6.990   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       4.343  -8.236   0.000  0.00  0.00          Cl+0
HETATM    9  N   UNK     0       3.913  -5.525   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       5.335   1.540   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20 Cl   UNK     0       8.002  -3.080   0.000  0.00  0.00          Cl+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   11   15                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₆Cl₄N₂O₄

Average Mass

383.9900 Da

Monoisotopic Mass

381.90817 Da

IUPAC Name

2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1H-pyrrole

Traditional Name

2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1H-pyrrole

CAS Registry Number

Not Available

SMILES

[O-][N+](=O)C1=C(NC(Cl)=C1Cl)C1OCOC2=C(Cl)C=C(Cl)C=C12

InChI Identifier

InChI=1S/C12H6Cl4N2O4/c13-4-1-5-10(6(14)2-4)21-3-22-11(5)8-9(18(19)20)7(15)12(16)17-8/h1-2,11,17H,3H2

InChI Key

CUPRKSFMHRXAFA-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
Streptomyces fumanus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzo-1,3-dioxanes. These are heterocyclic compounds containing a benzene ring fused to a 1,3-dioxane ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxanes

Sub Class

Benzo-1,3-dioxanes

Direct Parent

Benzo-1,3-dioxanes

Alternative Parents

Substituents

Benzo-1,3-dioxane
Nitroaromatic compound
Aryl chloride
Aryl halide
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
C-nitro compound
Organic nitro compound
Acetal
Organic oxoazanium
Oxacycle
Azacycle
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organic nitrogen compound
Organic zwitterion
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organohalogen compound
Organic salt
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	4.54	ALOGPS
logP	4.49	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	10.05	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.39 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.39 m³·mol⁻¹	ChemAxon
Polarizability	32.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4641129

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole (NP0166899)

MOL for NP0166899 (2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole)

3D MOL for NP0166899 (2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole)

3D SDF for NP0166899 (2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole)

3D-SDF for NP0166899 (2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole)

PDB for NP0166899 (2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole)

3D PDB for NP0166899 (2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole)

SMILES for NP0166899 (2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole)

INCHI for NP0166899 (2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole)

Structure for NP0166899 (2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole)

3D Structure for NP0166899 (2,3-dichloro-5-(6,8-dichloro-2,4-dihydro-1,3-benzodioxin-4-yl)-4-nitro-1h-pyrrole)