NP-MRD: Showing NP-Card for [4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate (NP0243673)

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Record Information

Version

2.0

Created at

2022-09-07 04:16:40 UTC

Updated at

2022-09-07 04:16:40 UTC

NP-MRD ID

NP0243673

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate

Description

[4-Chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2H-pyrrol-2-yl]methyl acetate belongs to the class of organic compounds known as 4-alkoxyphenols. These are phenols that carry an alkoxy group at the 4-position of the benzene ring. [4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate is found in Aspergillus egyptiacus. Based on a literature review very few articles have been published on [4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2H-pyrrol-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.5311    2.6999   -0.7027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6867    1.4944    0.1628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4549    1.6172    1.1537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0242    0.3027   -0.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2384   -0.7696    0.7692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5019   -2.0119    0.4264 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7959   -2.5694   -0.8440 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7924   -3.2295   -1.2833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7307   -3.9041   -2.4904 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3415   -3.1839   -0.3074 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8765   -3.1172   -1.1365 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0003   -1.8521    0.3948 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4043   -0.7833   -0.3977 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2129    0.2582   -0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674    0.3934    1.1850 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5927    1.4311    1.5730 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8869    2.4083    0.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7027    3.4812    0.9479 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3501    2.3165   -0.6276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5344    1.2722   -0.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6522    3.6183   -0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5908    2.6795   -1.2779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3987    2.6782   -1.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884   -0.4679    1.7939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3223   -1.0001    0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7240   -2.7706    1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -4.0691   -2.9926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2590   -3.9706    0.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803   -1.8600    1.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5689   -0.3419    1.9428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254    1.5333    2.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7038    3.4345    0.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5780    3.0886   -1.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125    1.1937   -1.9691 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  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 12  6  1  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  1
  9 27  1  0
 10 28  1  1
 12 29  1  1
 15 30  1  0
 16 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv1652309072206162D          

 20 21  0  0  0  0            999 V2000
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 O   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   -0.4741    0.0000 C   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 N   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1393   -3.2361    0.0000 Cl  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
    0.4131   -0.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715   -0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    0.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015    1.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8547    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262   -0.1701    0.0000 C   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  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  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
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243673

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1N=C(O)C(Cl)C1OC1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H14ClNO5/c1-7(16)19-6-10-12(11(14)13(18)15-10)20-9-4-2-8(17)3-5-9/h2-5,10-12,17H,6H2,1H3,(H,15,18)

> <INCHI_KEY>
WOFPPFMSFGKZQN-UHFFFAOYSA-N

> <FORMULA>
C13H14ClNO5

> <MOLECULAR_WEIGHT>
299.71

> <EXACT_MASS>
299.0560503

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.38372892438817

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2H-pyrrol-2-yl]methyl acetate

> <JCHEM_LOGP>
1.8018088426666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.912402285737953

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2393211537611872

> <JCHEM_PKA_STRONGEST_BASIC>
1.0415572383262455

> <JCHEM_POLAR_SURFACE_AREA>
88.35000000000001

> <JCHEM_REFRACTIVITY>
69.73110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2H-pyrrol-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.802   2.195   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.136  -0.115   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.048  -3.330   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.477  -6.041   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.032  -4.795   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       2.127  -6.041   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.091  -2.854   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.771  -1.348   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.693  -0.872   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.014   0.634   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.131   1.665   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.189   3.171   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.595   1.189   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.916  -0.317   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
[4-Chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2H-pyrrol-2-yl]methyl acetic acid	Generator

Chemical Formula

C₁₃H₁₄ClNO₅

Average Mass

299.7100 Da

Monoisotopic Mass

299.05605 Da

IUPAC Name

[4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2H-pyrrol-2-yl]methyl acetate

Traditional Name

[4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2H-pyrrol-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1N=C(O)C(Cl)C1OC1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C13H14ClNO5/c1-7(16)19-6-10-12(11(14)13(18)15-10)20-9-4-2-8(17)3-5-9/h2-5,10-12,17H,6H2,1H3,(H,15,18)

InChI Key

WOFPPFMSFGKZQN-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
Aspergillus egyptiacus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-alkoxyphenols. These are phenols that carry an alkoxy group at the 4-position of the benzene ring.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

4-alkoxyphenol
Phenoxy compound
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Cyclic carboximidic acid
Pyrroline
Lactim
Carboxylic acid ester
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
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	1.8	ChemAxon
pKa (Strongest Acidic)	3.24	ChemAxon
pKa (Strongest Basic)	1.04	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.35 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.73 m³·mol⁻¹	ChemAxon
Polarizability	28.38 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

163064072

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate (NP0243673)

MOL for NP0243673 ([4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate)

3D MOL for NP0243673 ([4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate)

3D SDF for NP0243673 ([4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate)

3D-SDF for NP0243673 ([4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate)

PDB for NP0243673 ([4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate)

3D PDB for NP0243673 ([4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate)

SMILES for NP0243673 ([4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate)

INCHI for NP0243673 ([4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate)

Structure for NP0243673 ([4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate)

3D Structure for NP0243673 ([4-chloro-5-hydroxy-3-(4-hydroxyphenoxy)-3,4-dihydro-2h-pyrrol-2-yl]methyl acetate)