NP-MRD: Showing NP-Card for 5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol (NP0259269)

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Record Information

Version

2.0

Created at

2022-09-08 01:04:47 UTC

Updated at

2022-09-08 01:04:47 UTC

NP-MRD ID

NP0259269

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol

Description

5-(2,4-Dimethylbenzyl) pyrrolidin-2-one belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions. 5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol was first documented in 2012 (PMID: 21782963). Based on a literature review a small amount of articles have been published on 5-(2,4-dimethylbenzyl) pyrrolidin-2-one (PMID: 22009268).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -4.4352    1.0915   -0.9887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0998    0.6727   -0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0274    1.5150   -0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7675    1.1753   -0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5260   -0.0444    0.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7586   -0.4998    0.9633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830    0.4513    0.6622 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1287    0.6727   -0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4336   -0.0203   -1.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0024   -0.2773    0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3276   -0.7529    0.5117 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1433   -0.0150    1.1910 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6220   -0.9063    0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4162   -2.2182    1.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8846   -0.5507    0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1800    0.3023   -0.8943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2792    1.4318   -2.0431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7030    1.9943   -0.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1783    2.4880   -1.0744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0381    1.8790   -0.2684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0334   -1.5300    0.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7538   -0.6072    2.0884 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6782    1.4037    1.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3119    0.2776   -1.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3097    1.7646   -0.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1432    0.6382   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2907   -0.9862   -1.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8875   -0.3563    1.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4360   -2.1429    2.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5366   -2.7705    0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995   -2.8596    0.9347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7326   -1.2203    0.2069 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  5 13  1  0
 13 14  1  0
 13 15  2  0
 15  2  1  0
 12  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  6 21  1  0
  6 22  1  0
  7 23  1  1
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 14 29  1  0
 14 30  1  0
 14 31  1  0
 15 32  1  0
M  END


  Mrv1652309082203042D          

 15 16  0  0  0  0            999 V2000
    2.2501    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5356    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0597    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203    2.2581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    1.5907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752    3.0428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1067    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    6.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212    6.0027    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
  3  4  1  0  0  0  0
  4  5  2  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
 10 12  2  0  0  0  0
  7 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  2 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259269

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC=C(CC2CCC(O)=N2)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H17NO/c1-9-3-4-11(10(2)7-9)8-12-5-6-13(15)14-12/h3-4,7,12H,5-6,8H2,1-2H3,(H,14,15)

> <INCHI_KEY>
PUUWMFZWQUAGCG-UHFFFAOYSA-N

> <FORMULA>
C13H17NO

> <MOLECULAR_WEIGHT>
203.285

> <EXACT_MASS>
203.131014171

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
23.680163966767303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2,4-dimethylphenyl)methyl]-3,4-dihydro-2H-pyrrol-5-ol

> <JCHEM_LOGP>
2.9299150952800863

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.5508086383809125

> <JCHEM_PKA_STRONGEST_BASIC>
6.5999939540837005

> <JCHEM_POLAR_SURFACE_AREA>
32.59

> <JCHEM_REFRACTIVITY>
61.8998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3H-pyrrol-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       4.200  11.205   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.867  10.435   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.867   8.895   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.533   8.125   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.199   8.895   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.134   8.125   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.134   6.585   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.111   5.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.364   4.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.904   4.215   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.810   2.969   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      -2.380   5.680   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.199  10.435   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.134  11.205   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.533  11.205   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    7                                                       
CONECT   13    5   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    2                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₇NO

Average Mass

203.2850 Da

Monoisotopic Mass

203.13101 Da

IUPAC Name

2-[(2,4-dimethylphenyl)methyl]-3,4-dihydro-2H-pyrrol-5-ol

Traditional Name

5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3H-pyrrol-2-ol

CAS Registry Number

Not Available

SMILES

CC1=CC=C(CC2CCC(O)=N2)C(C)=C1

InChI Identifier

InChI=1S/C13H17NO/c1-9-3-4-11(10(2)7-9)8-12-5-6-13(15)14-12/h3-4,7,12H,5-6,8H2,1-2H3,(H,14,15)

InChI Key

PUUWMFZWQUAGCG-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Xylenes

Direct Parent

m-Xylenes

Alternative Parents

Substituents

M-xylene
Pyrrolidone
2-pyrrolidone
Pyrrolidine
Carboxamide group
Lactam
Secondary carboxylic acid amide
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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	2.93	ChemAxon
pKa (Strongest Acidic)	4.55	ChemAxon
pKa (Strongest Basic)	6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.9 m³·mol⁻¹	ChemAxon
Polarizability	23.68 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

50912423

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

104687068

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Saurav K, Rajakumar G, Kannabiran K, Rahuman AA, Velayutham K, Elango G, Kamaraj C, Zahir AA: Larvicidal activity of isolated compound 5-(2,4-dimethylbenzyl) pyrrolidin-2-one from marine Streptomyces VITSVK5 sp. against Rhipicephalus (Boophilus) microplus, Anopheles stephensi, and Culex tritaeniorhynchus. Parasitol Res. 2013 Jan;112(1):215-26. doi: 10.1007/s00436-011-2682-z. Epub 2011 Oct 19. [PubMed:22009268 ]
Saurav K, Kannabiran K: In vitro activity of 5-(2,4-dimethylbenzyl) pyrrolidin-2-one extracted from marine Streptomyces VITSVK5 spp. against fungal and bacterial human pathogens. Rev Iberoam Micol. 2012 Jan-Mar;29(1):29-33. doi: 10.1016/j.riam.2011.06.008. Epub 2011 Jul 5. [PubMed:21782963 ]
LOTUS database [Link]

Showing NP-Card for 5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol (NP0259269)

MOL for NP0259269 (5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol)

3D MOL for NP0259269 (5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol)

3D SDF for NP0259269 (5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol)

3D-SDF for NP0259269 (5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol)

PDB for NP0259269 (5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol)

3D PDB for NP0259269 (5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol)

SMILES for NP0259269 (5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol)

INCHI for NP0259269 (5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol)

Structure for NP0259269 (5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol)

3D Structure for NP0259269 (5-[(2,4-dimethylphenyl)methyl]-4,5-dihydro-3h-pyrrol-2-ol)