NP-MRD: Showing NP-Card for (3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one (NP0292827)

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Record Information

Version

2.0

Created at

2022-09-10 00:33:01 UTC

Updated at

2022-09-10 00:33:01 UTC

NP-MRD ID

NP0292827

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one

Description

(3S)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8E)-icos-8-enoyl]pyrrolidin-2-one belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. (3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one is found in Amathia convoluta. Based on a literature review very few articles have been published on (3S)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8E)-icos-8-enoyl]pyrrolidin-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102202332D          

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M  END

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  Mrv1652309102202332D          

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   16.9167   -5.3709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1716   -4.5863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4687   -5.9840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2757   -5.8125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.2138   -6.7686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7658   -7.3817    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   16.4068   -6.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3027   -7.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0873   -7.5381    0.0000 O   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  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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  6  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 27 35  1  0  0  0  0
 25 36  1  0  0  0  0
 22 36  1  0  0  0  0
 36 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0292827

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCC\C=C\CCCCCCC(=O)N1CC[C@@](O)(C1=O)C1=CC(O)=C(Br)C(Br)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H45Br2NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-27(35)33-21-20-30(37,29(33)36)24-22-25(31)28(32)26(34)23-24/h12-13,22-23,34,37H,2-11,14-21H2,1H3/b13-12+/t30-/m0/s1

> <INCHI_KEY>
ZEXIDDZIAVCLOC-AMYCCCOXSA-N

> <FORMULA>
C30H45Br2NO4

> <MOLECULAR_WEIGHT>
643.501

> <EXACT_MASS>
641.171535

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
67.13695897278635

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8E)-icos-8-enoyl]pyrrolidin-2-one

> <JCHEM_LOGP>
9.395791553666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.061551372258695

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.282897849364179

> <JCHEM_PKA_STRONGEST_BASIC>
-4.143382091917169

> <JCHEM_POLAR_SURFACE_AREA>
77.84

> <JCHEM_REFRACTIVITY>
159.0367

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8E)-icos-8-enoyl]pyrrolidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       5.980 -23.740   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.314 -22.970   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.648 -23.740   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.981 -22.970   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.315 -23.740   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.649 -22.970   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.982 -23.740   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.316 -22.970   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.650 -23.740   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.983 -22.970   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      19.317 -23.740   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.651 -22.970   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.984 -23.740   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.318 -22.970   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.318 -21.430   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.652 -20.660   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      24.652 -19.120   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.986 -18.350   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.986 -16.810   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.319 -16.040   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      28.653 -16.810   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0      27.319 -14.500   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      26.073 -13.595   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      26.549 -12.131   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      28.089 -12.131   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      27.928 -10.599   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      29.596 -11.810   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      30.071 -10.346   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      31.578 -10.026   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      32.054  -8.561   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      32.608 -11.170   0.000  0.00  0.00           C+0
HETATM   32 Br   UNK     0      34.115 -10.850   0.000  0.00  0.00          Br+0
HETATM   33  C   UNK     0      32.132 -12.635   0.000  0.00  0.00           C+0
HETATM   34 Br   UNK     0      33.163 -13.779   0.000  0.00  0.00          Br+0
HETATM   35  C   UNK     0      30.626 -12.955   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      28.565 -13.595   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      30.030 -14.071   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   36                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   36                                             
CONECT   26   25                                                            
CONECT   27   25   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   27                                                       
CONECT   36   25   22   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₅Br₂NO₄

Average Mass

643.5010 Da

Monoisotopic Mass

641.17154 Da

IUPAC Name

(3S)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8E)-icos-8-enoyl]pyrrolidin-2-one

Traditional Name

(3S)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8E)-icos-8-enoyl]pyrrolidin-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCC\C=C\CCCCCCC(=O)N1CC[C@@](O)(C1=O)C1=CC(O)=C(Br)C(Br)=C1

InChI Identifier

InChI=1S/C30H45Br2NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-27(35)33-21-20-30(37,29(33)36)24-22-25(31)28(32)26(34)23-24/h12-13,22-23,34,37H,2-11,14-21H2,1H3/b13-12+/t30-/m0/s1

InChI Key

ZEXIDDZIAVCLOC-AMYCCCOXSA-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
Amathia convoluta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyrrolidines. These are polycyclic aromatic compounds containing a benzene ring linked to a pyrrolidine ring through a CC or CN bond. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolidines

Sub Class

Phenylpyrrolidines

Direct Parent

Phenylpyrrolidines

Alternative Parents

Substituents

3-phenylpyrrolidine
2-bromophenol
N-acylpyrrolidine
3-halophenol
2-halophenol
3-bromophenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Bromobenzene
Halobenzene
Pyrrolidone
2-pyrrolidone
Benzenoid
Monocyclic benzene moiety
Aryl halide
Carboxylic acid imide, n-substituted
Aryl bromide
Carboxylic acid imide
Dicarboximide
Tertiary alcohol
Pyrrole
Lactam
Azacycle
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
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	9.4	ChemAxon
pKa (Strongest Acidic)	7.28	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.84 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	159.04 m³·mol⁻¹	ChemAxon
Polarizability	67.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

163193820

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one (NP0292827)

MOL for NP0292827 ((3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one)

3D MOL for NP0292827 ((3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one)

3D SDF for NP0292827 ((3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one)

3D-SDF for NP0292827 ((3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one)

PDB for NP0292827 ((3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one)

3D PDB for NP0292827 ((3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one)

SMILES for NP0292827 ((3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one)

INCHI for NP0292827 ((3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one)

Structure for NP0292827 ((3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one)

3D Structure for NP0292827 ((3s)-3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-[(8e)-icos-8-enoyl]pyrrolidin-2-one)