NP-MRD: Showing NP-Card for 2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid (NP0219394)

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Record Information

Version

2.0

Created at

2022-09-05 20:22:04 UTC

Updated at

2022-09-05 20:22:05 UTC

NP-MRD ID

NP0219394

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid

Description

2-[(Dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group. 2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid is found in Acrodontium salmoneum. 2-[(Dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 32  0  0  0  0  0  0  0  0999 V2000
   -1.7046   -3.2408    1.2551 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0776   -2.0658    0.5461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1745   -2.0963   -0.0687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1904   -0.8439    0.5386 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8857    0.1957   -0.2982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1361    0.5047    0.2417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8112    1.4514   -0.4885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1353    2.9188    0.4969 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.3963    0.8141   -0.9821 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0968   -1.2949   -0.0581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1486   -1.7691   -1.3528 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1877   -0.2975   -0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3067    0.6702   -1.0238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3422    1.6086   -0.9972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2876    1.6048    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3414    2.5629    0.0261 N   0  0  0  0  0  4  0  0  0  0  0  0
    5.2095    2.6019    0.8962 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848    3.4932   -0.9828 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.1661    0.6293    0.9803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1409   -0.2948    0.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5037   -3.1828    2.2888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6198   -4.1699    0.7914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1062   -0.5332    1.5961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0526   -0.2193   -1.3109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2693    1.1147   -0.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2324    1.7882   -1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4027   -2.2248    0.5166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969   -2.3786   -1.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6009    0.7234   -1.8366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4269    2.3641   -1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9006    0.6184    1.7658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0525   -1.0527    1.7143 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  4 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 19  1  0
 19 20  2  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
 20 12  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  1
  5 24  1  0
  5 25  1  0
  7 26  1  0
 10 27  1  1
 11 28  1  0
 13 29  1  0
 14 30  1  0
 19 31  1  0
 20 32  1  0
M  CHG  2  16   1  18  -1
M  END


  Mrv1533004241506212D          

 20 20  0  0  0  0            999 V2000
    5.0013   -5.3625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 O   0  5  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  CHG  2  18   1  20  -1
M  END
> <DATABASE_ID>
NP0219394

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(=O)C(COC(Cl)Cl)C(O)C1=CC=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12Cl2N2O5/c12-11(13)20-5-8(10(14)17)9(16)6-1-3-7(4-2-6)15(18)19/h1-4,8-9,11,16H,5H2,(H2,14,17)

> <INCHI_KEY>
FHDPTOGOPLCNDA-UHFFFAOYSA-N

> <FORMULA>
C11H12Cl2N2O5

> <MOLECULAR_WEIGHT>
323.13

> <EXACT_MASS>
322.0123269

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
28.57490121781126

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanamide

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
1.3591737993333335

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.987436029087675

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.686401117689002

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2733924712385716

> <JCHEM_POLAR_SURFACE_AREA>
115.69000000000003

> <JCHEM_REFRACTIVITY>
72.24969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.89e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  N   UNK     0       9.336 -10.010   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       2.667  -7.700   0.000  0.00  0.00          Cl+0
HETATM    9 Cl   UNK     0       4.001  -5.390   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      14.670 -10.010   0.000  0.00  0.00           N+1
HETATM   19  O   UNK     0      16.004  -9.240   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.670 -11.550   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
2-[(Dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidate	Generator

Chemical Formula

C₁₁H₁₂Cl₂N₂O₅

Average Mass

323.1300 Da

Monoisotopic Mass

322.01233 Da

IUPAC Name

2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanamide

Traditional Name

2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanamide

CAS Registry Number

Not Available

SMILES

NC(=O)C(COC(Cl)Cl)C(O)C1=CC=C(C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C11H12Cl2N2O5/c12-11(13)20-5-8(10(14)17)9(16)6-1-3-7(4-2-6)15(18)19/h1-4,8-9,11,16H,5H2,(H2,14,17)

InChI Key

FHDPTOGOPLCNDA-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
Acrodontium salmoneum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrobenzenes. Nitrobenzenes are compounds containing a nitrobenzene moiety, which consists of a benzene ring with a carbon bearing a nitro group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Nitrobenzenes

Direct Parent

Nitrobenzenes

Alternative Parents

Substituents

Nitrobenzene
Nitroaromatic compound
Fatty amide
Fatty acyl
Carboxamide group
C-nitro compound
Primary carboxylic acid amide
Organic nitro compound
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Ether
Organic oxoazanium
Organic 1,3-dipolar compound
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organonitrogen compound
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alkyl halide
Alkyl chloride
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Aromatic alcohol
Organic zwitterion
Organic nitrogen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.18	ALOGPS
logP	1.36	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	13.69	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	115.69 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	72.25 m³·mol⁻¹	ChemAxon
Polarizability	28.57 Å³	ChemAxon
Number of Rings	1	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

177925

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid (NP0219394)

MOL for NP0219394 (2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid)

3D MOL for NP0219394 (2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid)

3D SDF for NP0219394 (2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid)

3D-SDF for NP0219394 (2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid)

PDB for NP0219394 (2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid)

3D PDB for NP0219394 (2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid)

SMILES for NP0219394 (2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid)

INCHI for NP0219394 (2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid)

Structure for NP0219394 (2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid)

3D Structure for NP0219394 (2-[(dichloromethoxy)methyl]-3-hydroxy-3-(4-nitrophenyl)propanimidic acid)