NP-MRD: Showing NP-Card for 4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one (NP0321761)

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Record Information

Version

2.0

Created at

2022-09-12 00:08:32 UTC

Updated at

2022-09-12 00:08:32 UTC

NP-MRD ID

NP0321761

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one

Description

Dysidamide belongs to the class of organic compounds known as n-acylpyrrolidines. These are n-Acylated Pyrrolidine derivatives. Pyrrolidine is a five-membered saturated aliphatic heterocycle with one nitrogen atom and four carbon atoms. 4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one is found in Lamellodysidea herbacea. Dysidamide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191518062D          

 25 25  0  0  0  0            999 V2000
   -1.4857    0.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706   -1.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350   -2.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5911   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4115   -1.2314    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5048   -0.4972    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6773   -2.1381    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200   -2.0713    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3025   -0.9190    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676   -1.8888    0.0000 Cl  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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
M  END


  Mrv1533004191518062D          

 25 25  0  0  0  0            999 V2000
   -1.4857    0.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0157    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1198    1.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1296   -1.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2857   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7706   -1.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4350   -2.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5911   -1.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4115   -1.2314    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.5048   -0.4972    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6773   -2.1381    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6351   -1.4039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1200   -2.0713    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3025   -0.9190    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676   -1.8888    0.0000 Cl  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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321761

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC1C(O)C(C)(C)C(=O)N1C(=O)CC(C)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl

> <INCHI_IDENTIFIER>
InChI=1S/C15H21Cl6NO3/c1-7(14(16,17)18)5-9-11(24)13(3,4)12(25)22(9)10(23)6-8(2)15(19,20)21/h7-9,11,24H,5-6H2,1-4H3

> <INCHI_KEY>
SZYKZXUJGUQVIX-UHFFFAOYSA-N

> <FORMULA>
C15H21Cl6NO3

> <MOLECULAR_WEIGHT>
476.04

> <EXACT_MASS>
472.9652597

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
42.979633423138424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one

> <ALOGPS_LOGP>
4.51

> <JCHEM_LOGP>
4.486520444666667

> <ALOGPS_LOGS>
-5.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.898181267919004

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2807355134122265

> <JCHEM_POLAR_SURFACE_AREA>
57.61

> <JCHEM_REFRACTIVITY>
104.70029999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.01e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -2.773   0.032   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.147  -1.375   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.029   3.224   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.090   3.224   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.770   1.651   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.735  -1.536   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.109  -2.943   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.267  -1.375   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.172  -2.621   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.545  -4.027   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.703  -2.460   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       8.235  -2.299   0.000  0.00  0.00          Cl+0
HETATM   20 Cl   UNK     0       6.542  -0.928   0.000  0.00  0.00          Cl+0
HETATM   21 Cl   UNK     0       6.864  -3.991   0.000  0.00  0.00          Cl+0
HETATM   22  C   UNK     0      -3.052  -2.621   0.000  0.00  0.00           C+0
HETATM   23 Cl   UNK     0      -3.957  -3.866   0.000  0.00  0.00          Cl+0
HETATM   24 Cl   UNK     0      -4.298  -1.715   0.000  0.00  0.00          Cl+0
HETATM   25 Cl   UNK     0      -1.806  -3.526   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22    2   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₁Cl₆NO₃

Average Mass

476.0400 Da

Monoisotopic Mass

472.96526 Da

IUPAC Name

4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one

Traditional Name

4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one

CAS Registry Number

Not Available

SMILES

CC(CC1C(O)C(C)(C)C(=O)N1C(=O)CC(C)C(Cl)(Cl)Cl)C(Cl)(Cl)Cl

InChI Identifier

InChI=1S/C15H21Cl6NO3/c1-7(14(16,17)18)5-9-11(24)13(3,4)12(25)22(9)10(23)6-8(2)15(19,20)21/h7-9,11,24H,5-6H2,1-4H3

InChI Key

SZYKZXUJGUQVIX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lamellodysidea herbacea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylpyrrolidines. These are n-Acylated Pyrrolidine derivatives. 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

N-acylpyrrolidines

Direct Parent

N-acylpyrrolidines

Alternative Parents

Substituents

N-acylpyrrolidine
Carboxylic acid imide, n-substituted
Pyrrolidone
2-pyrrolidone
Carboxylic acid imide
Dicarboximide
Lactam
Secondary alcohol
Carboxylic acid derivative
Azacycle
Organonitrogen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Alkyl halide
Alkyl chloride
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	4.51	ALOGPS
logP	4.49	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	13.9	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	104.7 m³·mol⁻¹	ChemAxon
Polarizability	42.98 Å³	ChemAxon
Number of Rings	1	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

361433

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one (NP0321761)

MOL for NP0321761 (4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one)

3D MOL for NP0321761 (4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one)

3D SDF for NP0321761 (4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one)

3D-SDF for NP0321761 (4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one)

PDB for NP0321761 (4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one)

3D PDB for NP0321761 (4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one)

SMILES for NP0321761 (4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one)

INCHI for NP0321761 (4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one)

Structure for NP0321761 (4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one)

3D Structure for NP0321761 (4-hydroxy-3,3-dimethyl-5-(3,3,3-trichloro-2-methylpropyl)-1-(4,4,4-trichloro-3-methylbutanoyl)pyrrolidin-2-one)