NP-MRD: Showing NP-Card for 4-benzoyl-3-nitrobenzene-1,2-diol (NP0281117)

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Record Information

Version

2.0

Created at

2022-09-09 07:16:14 UTC

Updated at

2022-09-09 07:16:14 UTC

NP-MRD ID

NP0281117

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-benzoyl-3-nitrobenzene-1,2-diol

Description

(3,4-DIHYDROXY-2-NITROPHENYL)(PHENYL)METHANONE belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups (3,4-DIHYDROXY-2-NITROPHENYL)(PHENYL)METHANONE is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -0.7898    2.5164    0.4321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001    1.2738    0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7472    0.4038    0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526   -0.9718    0.2107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7731   -1.7898    0.2677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0426   -1.2360    0.3412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1556    0.1209    0.3558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0289    0.9205    0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7575    0.9011   -0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2612    1.2775   -1.3730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5076    0.9135   -1.8099 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2812    0.1397   -0.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5691   -0.2628   -1.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8254   -0.2687    0.2591 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6628   -1.0318    1.0005 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5504    0.1242    0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0795   -0.2395    1.9622 N   0  0  0  0  0  4  0  0  0  0  0  0
    0.0447    0.3248    2.4051 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6881   -1.1284    2.8114 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.6844   -1.4484    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7151   -2.8648    0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9260   -1.8826    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1500    0.5470    0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1238    2.0074    0.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6632    1.8846   -2.0280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9159    1.2123   -2.7782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9312    0.0161   -2.2788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6516   -1.4590    1.8596 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  9 16  1  0
 16 14  2  0
 14 15  1  0
 16 17  1  0
 17 19  1  0
 17 18  2  0
 14 12  1  0
  8  3  1  0
 13 27  1  0
 11 26  1  0
 10 25  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  8 24  1  0
 15 28  1  0
M  CHG  2  17   1  19  -1
M  END

BIE
  Mrv0541 02241213262D          

 19 20  0  0  0  0            999 V2000
    0.9657    1.1670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2513    0.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2513   -0.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4632   -0.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4632   -1.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9657   -0.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6802   -0.0705    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.6802    0.7545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3947   -0.4830    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.9657   -1.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6802   -1.7205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2513   -1.7205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2513   -2.5455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4632    1.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1777    0.7545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4632    1.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1777    2.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8922    1.9920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8922    1.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  2  0  0  0  0
  3  6  1  0  0  0  0
  4  5  1  0  0  0  0
  5 12  2  0  0  0  0
  6  7  1  0  0  0  0
  6 10  2  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 19  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  CHG  2   7   1   9  -1
M  END
> <DATABASE_ID>
NP0281117

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C(=O)C2=CC=CC=C2)C(=C1O)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H9NO5/c15-10-7-6-9(11(13(10)17)14(18)19)12(16)8-4-2-1-3-5-8/h1-7,15,17H

> <INCHI_KEY>
ICLKAUQIPVFHOI-UHFFFAOYSA-N

> <FORMULA>
C13H9NO5

> <MOLECULAR_WEIGHT>
259.2143

> <EXACT_MASS>
259.048072403

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
24.367993177936633

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-benzoyl-3-nitrobenzene-1,2-diol

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.7654523993333333

> <ALOGPS_LOGS>
-3.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.90862131972226

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.202655612497769

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0450322414888165

> <JCHEM_POLAR_SURFACE_AREA>
103.35000000000001

> <JCHEM_REFRACTIVITY>
67.92000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-benzoyl-3-nitrobenzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: BIE                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       1.803   2.178   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.469   1.408   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.469  -0.132   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.865  -0.902   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.865  -2.442   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.803  -0.902   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.136  -0.132   0.000  0.00  0.00           N+1
HETATM    8  O   UNK     0       3.136   1.408   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.470  -0.902   0.000  0.00  0.00           O-1
HETATM   10  C   UNK     0       1.803  -2.442   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.136  -3.212   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.469  -3.212   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.469  -4.752   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.865   2.178   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.198   1.408   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.865   3.718   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.198   4.488   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.532   3.718   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.532   2.178   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4   12                                                       
CONECT    6    3    7   10                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    6   11   12                                                  
CONECT   11   10                                                            
CONECT   12    5   10   13                                                  
CONECT   13   12                                                            
CONECT   14    2   15   16                                                  
CONECT   15   14   19                                                       
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   15   18                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dihydroxy-2-nitrobenzophenone	MeSH
BIA 8-176	MeSH
BIA-8-176	MeSH

Chemical Formula

C₁₃H₉NO₅

Average Mass

259.2143 Da

Monoisotopic Mass

259.04807 Da

IUPAC Name

4-benzoyl-3-nitrobenzene-1,2-diol

Traditional Name

4-benzoyl-3-nitrobenzene-1,2-diol

CAS Registry Number

Not Available

SMILES

OC1=CC=C(C(=O)C2=CC=CC=C2)C(=C1O)[N+]([O-])=O

InChI Identifier

InChI=1S/C13H9NO5/c15-10-7-6-9(11(13(10)17)14(18)19)12(16)8-4-2-1-3-5-8/h1-7,15,17H

InChI Key

ICLKAUQIPVFHOI-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzophenones

Direct Parent

Benzophenones

Alternative Parents

Substituents

Benzophenone
Diphenylmethane
Aryl-phenylketone
Nitrophenol
Nitrobenzene
Nitroaromatic compound
Benzoyl
Catechol
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Ketone
C-nitro compound
Organic nitro compound
Organic oxoazanium
Organic 1,3-dipolar compound
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organopnictogen compound
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	2.36	ALOGPS
logP	2.77	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.2	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.35 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	67.92 m³·mol⁻¹	ChemAxon
Polarizability	24.37 Å³	ChemAxon
Number of Rings	2	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

DB07462

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

6914595

PDB ID

BIE

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-benzoyl-3-nitrobenzene-1,2-diol (NP0281117)

MOL for NP0281117 (4-benzoyl-3-nitrobenzene-1,2-diol)

3D MOL for NP0281117 (4-benzoyl-3-nitrobenzene-1,2-diol)

3D SDF for NP0281117 (4-benzoyl-3-nitrobenzene-1,2-diol)

3D-SDF for NP0281117 (4-benzoyl-3-nitrobenzene-1,2-diol)

PDB for NP0281117 (4-benzoyl-3-nitrobenzene-1,2-diol)

3D PDB for NP0281117 (4-benzoyl-3-nitrobenzene-1,2-diol)

SMILES for NP0281117 (4-benzoyl-3-nitrobenzene-1,2-diol)

INCHI for NP0281117 (4-benzoyl-3-nitrobenzene-1,2-diol)

Structure for NP0281117 (4-benzoyl-3-nitrobenzene-1,2-diol)

3D Structure for NP0281117 (4-benzoyl-3-nitrobenzene-1,2-diol)