NP-MRD: Showing NP-Card for (4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester (NP0007092)

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Record Information

Version

2.0

Created at

2020-12-09 03:58:55 UTC

Updated at

2021-07-15 16:56:38 UTC

NP-MRD ID

NP0007092

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester

Provided By

NPAtlas

Description

Methyl 2-(4-hydroxy-3,5-dinitrophenyl)acetate belongs to the class of organic compounds known as dinitrophenols. These are organic aromatic compounds containing a benzene that carries a single phenol group and exactly two nitro groups. (4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester is found in Salegentibacter sp. T436. Based on a literature review very few articles have been published on methyl 2-(4-hydroxy-3,5-dinitrophenyl)acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118373D          

 26 26  0  0  0  0            999 V2000
    4.7276    0.4972    0.8986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7794    0.2984   -0.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4310    0.2080    0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9582    0.3008    1.2091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125    0.0005   -1.0781 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0952   -0.0724   -0.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194    1.0302   -0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0658    0.9456   -0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8396    2.1412   -0.0697 N   0  3  0  0  0  4  0  0  0  0  0  0
   -3.7426    2.3655    0.7257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5064    3.1389   -0.9838 O   0  5  0  0  0  1  0  0  0  0  0  0
   -2.6079   -0.2764    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9219   -0.4197    0.5402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7958   -1.4056    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3803   -2.6638    0.3553 N   0  3  0  0  0  4  0  0  0  0  0  0
   -3.5922   -2.9118    0.1521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6287   -3.6738    0.9019 O   0  5  0  0  0  1  0  0  0  0  0  0
   -0.4817   -1.2884   -0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576    1.5352    0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2947    0.4179    1.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753   -0.1851    0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6958    0.8462   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077   -0.9204   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2896    1.9855   -0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6210    0.2754    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1577   -2.1689   -0.4336 H   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  2  0  0  0  0
 18  6  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  5 22  1  0  0  0  0
  5 23  1  0  0  0  0
  7 24  1  0  0  0  0
 13 25  1  0  0  0  0
 18 26  1  0  0  0  0
M  CHG  4   9   1  11  -1  15   1  17  -1
M  END


  Mrv1652306242118373D          

 26 26  0  0  0  0            999 V2000
    4.7276    0.4972    0.8986 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7794    0.2984   -0.1384 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4310    0.2080    0.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9582    0.3008    1.2091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125    0.0005   -1.0781 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0952   -0.0724   -0.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7194    1.0302   -0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0658    0.9456   -0.1530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8396    2.1412   -0.0697 N   0  3  0  0  0  4  0  0  0  0  0  0
   -3.7426    2.3655    0.7257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5064    3.1389   -0.9838 O   0  5  0  0  0  1  0  0  0  0  0  0
   -2.6079   -0.2764    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9219   -0.4197    0.5402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7958   -1.4056    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3803   -2.6638    0.3553 N   0  3  0  0  0  4  0  0  0  0  0  0
   -3.5922   -2.9118    0.1521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6287   -3.6738    0.9019 O   0  5  0  0  0  1  0  0  0  0  0  0
   -0.4817   -1.2884   -0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1576    1.5352    0.8092 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2947    0.4179    1.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5753   -0.1851    0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6958    0.8462   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8077   -0.9204   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2896    1.9855   -0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6210    0.2754    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1577   -2.1689   -0.4336 H   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 14 18  2  0  0  0  0
 18  6  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  5 22  1  0  0  0  0
  5 23  1  0  0  0  0
  7 24  1  0  0  0  0
 13 25  1  0  0  0  0
 18 26  1  0  0  0  0
M  CHG  4   9   1  11  -1  15   1  17  -1
M  END
> <DATABASE_ID>
NP0007092

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C([H])=C(C([H])=C1[N+]([O-])=O)C([H])([H])C(=O)OC([H])([H])[H])[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H8N2O7/c1-18-8(12)4-5-2-6(10(14)15)9(13)7(3-5)11(16)17/h2-3,13H,4H2,1H3

> <INCHI_KEY>
JEPPUCFMMDZCPE-UHFFFAOYSA-N

> <FORMULA>
C9H8N2O7

> <MOLECULAR_WEIGHT>
256.17

> <EXACT_MASS>
256.033150606

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
22.101732335059353

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{[2-hydroxy-5-(2-methoxy-2-oxoethyl)-3-nitrophenyl]nitro}-lambda1-oxidanyl

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
1.3332912183333332

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.611432895251777

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.101495305977088

> <JCHEM_PKA_STRONGEST_BASIC>
-7.075085890190684

> <JCHEM_POLAR_SURFACE_AREA>
132.81

> <JCHEM_REFRACTIVITY>
56.75660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[2-hydroxy-5-(2-methoxy-2-oxoethyl)-3-nitrophenylnitro]-lambda1-oxidanyl

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.728   0.497   0.899  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.779   0.298  -0.138  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.431   0.208   0.059  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.958   0.301   1.209  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.513   0.001  -1.078  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.095  -0.072  -0.659  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.719   1.030  -0.552  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.066   0.946  -0.153  0.00  0.00           C+0
HETATM    9  N   UNK     0      -2.840   2.141  -0.070  0.00  0.00           N+1
HETATM   10  O   UNK     0      -3.743   2.365   0.726  0.00  0.00           O+0
HETATM   11  O   UNK     0      -2.506   3.139  -0.984  0.00  0.00           O-1
HETATM   12  C   UNK     0      -2.608  -0.276   0.146  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.922  -0.420   0.540  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.796  -1.406   0.043  0.00  0.00           C+0
HETATM   15  N   UNK     0      -2.380  -2.664   0.355  0.00  0.00           N+1
HETATM   16  O   UNK     0      -3.592  -2.912   0.152  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.629  -3.674   0.902  0.00  0.00           O-1
HETATM   18  C   UNK     0      -0.482  -1.288  -0.351  0.00  0.00           C+0
HETATM   19  H   UNK     0       5.158   1.535   0.809  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.295   0.418   1.893  0.00  0.00           H+0
HETATM   21  H   UNK     0       5.575  -0.185   0.699  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.696   0.846  -1.805  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.808  -0.920  -1.665  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.290   1.986  -0.788  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.621   0.275   0.653  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.158  -2.169  -0.434  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   22   23                                             
CONECT    6    5    7   18                                                  
CONECT    7    6    8   24                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13   14                                                  
CONECT   13   12   25                                                       
CONECT   14   12   15   18                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   14    6   26                                                  
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    5                                                            
CONECT   23    5                                                            
CONECT   24    7                                                            
CONECT   25   13                                                            
CONECT   26   18                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl 2-(4-hydroxy-3,5-dinitrophenyl)acetic acid	Generator
Methyl 2-(3,5-dinitro-4-hydroxyphenyl)acetic acid	Generator

Chemical Formula

C₉H₈N₂O₇

Average Mass

256.1700 Da

Monoisotopic Mass

256.03315 Da

IUPAC Name

{[2-hydroxy-5-(2-methoxy-2-oxoethyl)-3-nitrophenyl]nitro}-lambda1-oxidanyl

Traditional Name

[2-hydroxy-5-(2-methoxy-2-oxoethyl)-3-nitrophenylnitro]-lambda1-oxidanyl

CAS Registry Number

Not Available

SMILES

COC(=O)CC1=CC(=C(O)C(=C1)[N+]([O-])=O)[N+]([O-])=O

InChI Identifier

InChI=1S/C9H8N2O7/c1-18-8(12)4-5-2-6(10(14)15)9(13)7(3-5)11(16)17/h2-3,13H,4H2,1H3

InChI Key

JEPPUCFMMDZCPE-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Salegentibacter sp. T436	NPAtlas	17551208

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dinitrophenols. These are organic aromatic compounds containing a benzene that carries a single phenol group and exactly two nitro groups.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Dinitrophenol
Nitrobenzene
Nitroaromatic compound
Monocyclic benzene moiety
Methyl ester
Carboxylic acid ester
Organic nitro compound
C-nitro compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic cation
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	1.73	ALOGPS
logP	1.33	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.1	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	132.81 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	56.76 m³·mol⁻¹	ChemAxon
Polarizability	22.1 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

NPAtlas ID

NPA008691

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

16047838

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22938302

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester (NP0007092)

MOL for NP0007092 ((4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester)

3D MOL for NP0007092 ((4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester)

3D SDF for NP0007092 ((4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester)

3D-SDF for NP0007092 ((4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester)

PDB for NP0007092 ((4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester)

3D PDB for NP0007092 ((4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester)

SMILES for NP0007092 ((4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester)

INCHI for NP0007092 ((4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester)

Structure for NP0007092 ((4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester)

3D Structure for NP0007092 ((4-Hydroxy-3,5-dinitrophenyl)acetic acid methyl ester)