NP-MRD: Showing NP-Card for {5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid (NP0165665)

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Record Information

Version

2.0

Created at

2022-09-03 00:52:15 UTC

Updated at

2022-09-03 00:52:15 UTC

NP-MRD ID

NP0165665

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid

Description

2-{2-[(3-Chloro-4-hydroxyphenyl)methylidene]-3,5-dihydroxy-2H-pyrrol-4-yl}-2-oxoacetic acid belongs to the class of organic compounds known as o-chlorophenols. These are chlorophenols carrying a iodine at the C2 position of the benzene ring. {5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid is found in Rossbeevera pachydermis. 2-{2-[(3-Chloro-4-hydroxyphenyl)methylidene]-3,5-dihydroxy-2H-pyrrol-4-yl}-2-oxoacetic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    4.8277    1.4736    0.5283 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0822    0.2613    0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4762   -0.0106    0.3399 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1678   -0.8073    0.1217 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6600   -1.9623   -0.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7272   -0.6730    0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9496    0.3790    0.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3949    1.6949    0.5343 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5371    0.0652    0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4707    0.9409    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8590    0.6063    0.2825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7537    1.0418    1.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0977    0.7660    1.2399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6344    0.0267    0.2061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9724   -0.2836    0.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7843   -0.4168   -0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4506   -1.3520   -2.1020 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.4139   -0.1277   -0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4438   -1.3109   -0.0426 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7680   -1.7954   -0.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1472   -2.9785   -0.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0681    0.4959   -0.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0735    2.3832   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2175    1.9898    0.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3074    1.6271    2.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7524    1.1237    2.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4018   -0.8123   -0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7687   -0.4949   -1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4388   -1.8500   -0.1522 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 19  1  0
 19 20  1  0
 20 21  2  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 20  6  1  0
 18 11  1  0
  3 22  1  0
  8 23  1  0
 19 29  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 18 28  1  0
M  END


  Mrv1533004181501402D          

 21 22  0  0  0  0            999 V2000
    1.3222    0.7634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341   -3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5986   -3.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0835   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7479   -5.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -5.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5919   -6.2508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4425   -4.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6221   -4.9159    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7781   -4.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 O   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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  4  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 11 18  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0165665

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(=O)C1=C(O)C(NC1=O)=CC1=CC=C(O)C(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H8ClNO6/c14-6-3-5(1-2-8(6)16)4-7-10(17)9(12(19)15-7)11(18)13(20)21/h1-4,16-17H,(H,15,19)(H,20,21)

> <INCHI_KEY>
XYHLQFZGLAWUCL-UHFFFAOYSA-N

> <FORMULA>
C13H8ClNO6

> <MOLECULAR_WEIGHT>
309.66

> <EXACT_MASS>
309.0040147

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
27.96009856367334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{5-[(3-chloro-4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrol-3-yl}-2-oxoacetic acid

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
0.9035616523333332

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.828113555001147

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5455603198944012

> <JCHEM_PKA_STRONGEST_BASIC>
-6.691395914159551

> <JCHEM_POLAR_SURFACE_AREA>
123.93

> <JCHEM_REFRACTIVITY>
73.8267

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{5-[(3-chloro-4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxo-1H-pyrrol-3-yl}(oxo)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-APR-15         0                                  
HETATM    1  O   UNK     0       2.468   1.425   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.468  -0.115   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.134  -0.885   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.136  -0.115   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.512  -2.854   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.477  -6.041   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.851  -7.448   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.756  -8.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.129 -10.100   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.598 -10.261   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.972 -11.668   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.693  -9.015   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0       1.161  -9.176   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0       3.319  -7.609   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       3.032  -4.795   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.091  -2.854   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   20                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11                                                       
CONECT   19    9   20                                                       
CONECT   20   19    6   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
2-{2-[(3-chloro-4-hydroxyphenyl)methylidene]-3,5-dihydroxy-2H-pyrrol-4-yl}-2-oxoacetate	Generator

Chemical Formula

C₁₃H₈ClNO₆

Average Mass

309.6600 Da

Monoisotopic Mass

309.00401 Da

IUPAC Name

2-{5-[(3-chloro-4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrol-3-yl}-2-oxoacetic acid

Traditional Name

{5-[(3-chloro-4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxo-1H-pyrrol-3-yl}(oxo)acetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C(=O)C1=C(O)C(NC1=O)=CC1=CC=C(O)C(Cl)=C1

InChI Identifier

InChI=1S/C13H8ClNO6/c14-6-3-5(1-2-8(6)16)4-7-10(17)9(12(19)15-7)11(18)13(20)21/h1-4,16-17H,(H,15,19)(H,20,21)

InChI Key

XYHLQFZGLAWUCL-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
Rossbeevera pachydermis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-chlorophenols. These are chlorophenols carrying a iodine at the C2 position of the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

2-chlorophenol
1-hydroxy-2-unsubstituted benzenoid
Chlorobenzene
Halobenzene
Alpha-keto acid
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Keto acid
Alpha-hydroxy ketone
Vinylogous acid
Cyclic carboximidic acid
Ketone
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Carboxylic acid
Azacycle
Enol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organohalogen compound
Organochloride
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.62	ALOGPS
logP	0.9	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.55	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	123.93 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	73.83 m³·mol⁻¹	ChemAxon
Polarizability	27.96 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

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

76170588

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid (NP0165665)

MOL for NP0165665 ({5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid)

3D MOL for NP0165665 ({5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid)

3D SDF for NP0165665 ({5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid)

3D-SDF for NP0165665 ({5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid)

PDB for NP0165665 ({5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid)

3D PDB for NP0165665 ({5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid)

SMILES for NP0165665 ({5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid)

INCHI for NP0165665 ({5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid)

Structure for NP0165665 ({5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid)

3D Structure for NP0165665 ({5-[(3-chloro-4-hydroxyphenyl)methylidene]-2,4-dihydroxypyrrol-3-yl}(oxo)acetic acid)