NP-MRD: Showing NP-Card for 3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one (NP0147449)

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Record Information

Version

2.0

Created at

2022-09-02 03:03:36 UTC

Updated at

2022-09-02 03:03:36 UTC

NP-MRD ID

NP0147449

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one

Description

3-(3,4-Dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-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. 3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one is found in Amathia convoluta. 3-(3,4-Dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251508352D          

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M  END

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  Mrv1533004251508352D          

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 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  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  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  2  0  0  0  0
 23 27  1  0  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
M  END
> <DATABASE_ID>
NP0147449

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCC(=O)N1CCC(O)(C1=O)C1=CC(O)=C(Br)C(Br)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H43Br2NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-25(33)31-19-18-28(35,27(31)34)22-20-23(29)26(30)24(32)21-22/h20-21,32,35H,2-19H2,1H3

> <INCHI_KEY>
HBSJNCNRIRVIQL-UHFFFAOYSA-N

> <FORMULA>
C28H43Br2NO4

> <MOLECULAR_WEIGHT>
617.463

> <EXACT_MASS>
615.155885

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
64.0631605440516

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one

> <ALOGPS_LOGP>
7.70

> <JCHEM_LOGP>
8.868575880333333

> <ALOGPS_LOGS>
-6.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.06155137225893

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.282897849364179

> <JCHEM_PKA_STRONGEST_BASIC>
-4.143382091917066

> <JCHEM_POLAR_SURFACE_AREA>
77.84

> <JCHEM_REFRACTIVITY>
148.71809999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.89e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      19.522 -17.385   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.856 -18.155   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.190 -17.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.523 -18.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.857 -17.385   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.191 -18.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.524 -17.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      28.858 -18.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.192 -17.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      31.525 -18.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.859 -17.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      34.193 -18.155   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.526 -17.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.860 -18.155   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      38.194 -17.385   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      39.527 -18.155   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      40.861 -17.385   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      42.195 -18.155   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      42.195 -19.695   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      43.528 -17.385   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      43.689 -15.853   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      45.196 -15.533   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      45.966 -16.866   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      47.212 -15.961   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      44.935 -18.011   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      45.255 -19.517   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      46.996 -18.011   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      48.503 -17.691   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      49.533 -18.835   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      51.039 -18.515   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      49.057 -20.300   0.000  0.00  0.00           C+0
HETATM   32 Br   UNK     0      50.088 -21.444   0.000  0.00  0.00          Br+0
HETATM   33  C   UNK     0      47.551 -20.620   0.000  0.00  0.00           C+0
HETATM   34 Br   UNK     0      47.075 -22.085   0.000  0.00  0.00          Br+0
HETATM   35  C   UNK     0      46.520 -19.476   0.000  0.00  0.00           C+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   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   27                                             
CONECT   24   23                                                            
CONECT   25   23   20   26                                                  
CONECT   26   25                                                            
CONECT   27   23   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                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₃Br₂NO₄

Average Mass

617.4630 Da

Monoisotopic Mass

615.15588 Da

IUPAC Name

3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one

Traditional Name

3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCC(=O)N1CCC(O)(C1=O)C1=CC(O)=C(Br)C(Br)=C1

InChI Identifier

InChI=1S/C28H43Br2NO4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-25(33)31-19-18-28(35,27(31)34)22-20-23(29)26(30)24(32)21-22/h20-21,32,35H,2-19H2,1H3

InChI Key

HBSJNCNRIRVIQL-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
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-bromophenol
2-halophenol
3-halophenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Bromobenzene
Halobenzene
Monocyclic benzene moiety
Aryl halide
Pyrrolidone
2-pyrrolidone
Carboxylic acid imide, n-substituted
Benzenoid
Aryl bromide
Carboxylic acid imide
Dicarboximide
Tertiary alcohol
Pyrrole
Lactam
Azacycle
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	7.7	ALOGPS
logP	8.87	ChemAxon
logS	-6.8	ALOGPS
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	17	ChemAxon
Refractivity	148.72 m³·mol⁻¹	ChemAxon
Polarizability	64.06 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

10100372

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one (NP0147449)

MOL for NP0147449 (3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one)

3D MOL for NP0147449 (3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one)

3D SDF for NP0147449 (3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one)

3D-SDF for NP0147449 (3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one)

PDB for NP0147449 (3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one)

3D PDB for NP0147449 (3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one)

SMILES for NP0147449 (3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one)

INCHI for NP0147449 (3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one)

Structure for NP0147449 (3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one)

3D Structure for NP0147449 (3-(3,4-dibromo-5-hydroxyphenyl)-3-hydroxy-1-octadecanoylpyrrolidin-2-one)