NP-MRD: Showing NP-Card for 5-nitroresorcinol (NP0008076)

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Record Information

Version

2.0

Created at

2020-12-09 05:42:32 UTC

Updated at

2021-07-15 16:59:21 UTC

NP-MRD ID

NP0008076

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-nitroresorcinol

Provided By

NPAtlas

Description

5-nitroresorcinol is found in Stigmatella and Stigmatella erecta. 5-nitroresorcinol was first documented in 2008 (PMID: 18986196). Based on a literature review very few articles have been published on 5-nitroresorcinol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106063D          

 16 16  0  0  0  0            999 V2000
    3.3503   -0.4214   -0.1531 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3055   -1.1000   -0.1201 N   0  3  0  0  0  4  0  0  0  0  0  0
    2.4578   -2.4644   -0.1199 O   0  5  0  0  0  1  0  0  0  0  0  0
    1.0270   -0.4741   -0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628    0.8886   -0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903    1.4793   -0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641    2.8494   -0.0495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5234    0.6924   -0.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3808   -0.6804   -0.0134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079   -1.5046    0.0225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1065   -1.2585   -0.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235    1.5256   -0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    3.5190   -0.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5281    1.0878    0.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854   -1.7968    0.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115   -2.3420   -0.0479 H   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  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11  4  1  0  0  0  0
  5 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
M  CHG  2   2   1   3  -1
M  END
> <DATABASE_ID>
NP0008076

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H5NO4/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,8-9H

> <INCHI_KEY>
VNIXZWLYQDIGNU-UHFFFAOYSA-N

> <FORMULA>
C6H5NO4

> <MOLECULAR_WEIGHT>
155.109

> <EXACT_MASS>
155.021857645

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
13.354551905886012

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(3,5-dihydroxyphenyl)nitro]-lambda1-oxidanyl

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
1.3060993619999999

> <ALOGPS_LOGS>
-1.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.100568411065662

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.631994925046528

> <JCHEM_PKA_STRONGEST_BASIC>
-5.805110547661092

> <JCHEM_POLAR_SURFACE_AREA>
83.60000000000001

> <JCHEM_REFRACTIVITY>
36.3403

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.11e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3,5-dihydroxyphenylnitro)-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  O   UNK     0       3.350  -0.421  -0.153  0.00  0.00           O+0
HETATM    2  N   UNK     0       2.305  -1.100  -0.120  0.00  0.00           N+1
HETATM    3  O   UNK     0       2.458  -2.464  -0.120  0.00  0.00           O-1
HETATM    4  C   UNK     0       1.027  -0.474  -0.085  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.863   0.889  -0.085  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.390   1.479  -0.050  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.564   2.849  -0.050  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.523   0.692  -0.014  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.381  -0.680  -0.013  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.508  -1.505   0.023  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.107  -1.258  -0.049  0.00  0.00           C+0
HETATM   12  H   UNK     0       1.724   1.526  -0.112  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.171   3.519  -0.073  0.00  0.00           H+0
HETATM   14  H   UNK     0      -2.528   1.088   0.014  0.00  0.00           H+0
HETATM   15  H   UNK     0      -2.885  -1.797   0.934  0.00  0.00           H+0
HETATM   16  H   UNK     0      -0.012  -2.342  -0.048  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6   12                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   13                                                       
CONECT    8    6    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9   15                                                       
CONECT   11    9    4   16                                                  
CONECT   12    5                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15   10                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₆H₅NO₄

Average Mass

155.1090 Da

Monoisotopic Mass

155.02186 Da

IUPAC Name

[(3,5-dihydroxyphenyl)nitro]-lambda1-oxidanyl

Traditional Name

(3,5-dihydroxyphenylnitro)-lambda1-oxidanyl

CAS Registry Number

Not Available

SMILES

OC1=CC(=CC(O)=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C6H5NO4/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,8-9H

InChI Key

VNIXZWLYQDIGNU-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
Stigmatella	NPAtlas	18986196
Stigmatella erecta	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as nitrophenols. These are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Nitrophenol
Nitrobenzene
Nitroaromatic compound
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
C-nitro compound
Organic nitro compound
Organic oxoazanium
Allyl-type 1,3-dipolar organic compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic salt
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organic oxide
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	1.35	ALOGPS
logP	1.31	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	7.63	ChemAxon
pKa (Strongest Basic)	-5.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.34 m³·mol⁻¹	ChemAxon
Polarizability	13.35 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA005686

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8803230

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10627867

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hofle G, Irschik H: Isolation and biosynthesis of aurachin P and 5-nitroresorcinol from Stigmatella erecta. J Nat Prod. 2008 Nov;71(11):1946-8. doi: 10.1021/np800325z. Epub 2008 Nov 6. [PubMed:18986196 ]

Showing NP-Card for 5-nitroresorcinol (NP0008076)

MOL for NP0008076 (5-nitroresorcinol)

3D MOL for NP0008076 (5-nitroresorcinol)

3D SDF for NP0008076 (5-nitroresorcinol)

3D-SDF for NP0008076 (5-nitroresorcinol)

PDB for NP0008076 (5-nitroresorcinol)

3D PDB for NP0008076 (5-nitroresorcinol)

SMILES for NP0008076 (5-nitroresorcinol)

INCHI for NP0008076 (5-nitroresorcinol)

Structure for NP0008076 (5-nitroresorcinol)

3D Structure for NP0008076 (5-nitroresorcinol)