NP-MRD: Showing NP-Card for Lansimide 3 (NP0086367)

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Record Information

Version

2.0

Created at

2022-04-29 06:40:15 UTC

Updated at

2022-04-29 06:40:15 UTC

NP-MRD ID

NP0086367

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lansimide 3

Description

Lansimide 3 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. Lansimide 3 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Lansimide 3 has been detected, but not quantified in, fruits. Lansimide 3 is found in Clausena lansium . This could make lansimide 3 a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    2.7864   -2.2936   -0.7607 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1491   -1.6188    0.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1082   -0.7708   -0.2416 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5628    0.6110    0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9154    1.0306    1.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3647    2.3351    1.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4683    3.2417    0.5171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1146    2.8229   -0.7469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6662    1.5140   -0.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208   -1.2224    0.4383 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4457   -0.7594   -0.0657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8448    0.6017    0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5001    0.9221    1.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9224    2.2095    1.6533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7026    3.2353    0.7600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0505    2.9304   -0.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6354    1.6337   -0.6746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4054   -1.2075   -1.4867 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6497   -1.4188   -2.0435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7770   -2.5704   -1.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7354   -3.4659   -2.1522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2451   -2.6500    0.0393 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0869   -3.8117    0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0557   -2.9151   -1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1982   -1.5887   -1.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5553   -2.9833   -0.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0986   -0.9260   -1.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8416    0.3360    2.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6398    2.6447    2.5643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8209    4.2469    0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920    3.5277   -1.5699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4033    1.2445   -1.9690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0444   -1.2019    1.5486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1858   -1.4958    0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6815    0.1164    2.0931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4376    2.4709    2.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0368    4.2625    0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8664    3.7188   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1378    1.4704   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8136   -0.5876   -2.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3987   -1.3468   -1.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6680   -4.5028    0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7235   -3.4731    1.6640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7820   -4.3164    1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 10  1  0
 10 11  1  0
 11 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
 22 10  1  0
 17 12  1  0
  9  4  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  6
 10 33  1  1
 11 34  1  1
 18 40  1  6
 19 41  1  0
 23 42  1  0
 23 43  1  0
 23 44  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
M  END


  Mrv0541 02241208042D          

 23 25  0  0  0  0            999 V2000
   -0.5322   -2.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703   -2.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0071   -2.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0897   -1.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4342   -1.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6149   -1.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0253   -2.0898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786   -1.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406   -1.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0406   -0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6149    0.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4342    0.0405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2703    1.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877    2.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4495    2.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2871    2.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2044    1.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5322    1.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897   -0.6150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2703   -0.6150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7786    0.0405    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1877    0.7772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0555    0.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 20  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 21  1  0  0  0  0
 11 12  1  0  0  0  0
 11 18  1  0  0  0  0
 12 23  1  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086367

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(C1C(C(O)C(=O)N1C)C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H21NO3/c1-20-16(18(23-2)14-11-7-4-8-12-14)15(17(21)19(20)22)13-9-5-3-6-10-13/h3-12,15-18,21H,1-2H3

> <INCHI_KEY>
MNNOPIIJDXUZST-UHFFFAOYSA-N

> <FORMULA>
C19H21NO3

> <MOLECULAR_WEIGHT>
311.3749

> <EXACT_MASS>
311.152143543

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.0847227564073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-5-[methoxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
2.1103661216666656

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.78163666516144

> <JCHEM_PKA_STRONGEST_BASIC>
-3.769110935701085

> <JCHEM_POLAR_SURFACE_AREA>
49.77

> <JCHEM_REFRACTIVITY>
88.1111

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-5-[methoxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.993  -4.361   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.371  -5.279   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.747  -4.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.901  -3.137   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.677  -2.217   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.148  -2.829   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.914  -3.901   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.453  -2.371   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.076  -1.911   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.076  -0.384   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.148   0.533   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.677   0.076   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.371   2.980   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.217   4.513   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.839   5.279   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.536   4.358   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.382   2.829   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.993   2.066   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.901  -1.148   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.371  -1.148   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.453   0.076   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       2.217   1.451   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.837   1.172   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    9                                                  
CONECT    7    8                                                            
CONECT    8    7    9   20                                                  
CONECT    9    6    8   10                                                  
CONECT   10    9   11   21                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   23                                                       
CONECT   13   14   18                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   11   13   17                                                  
CONECT   19   20                                                            
CONECT   20    8   19   21                                                  
CONECT   21   10   20   22                                                  
CONECT   22   21                                                            
CONECT   23   12                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₁NO₃

Average Mass

311.3749 Da

Monoisotopic Mass

311.15214 Da

IUPAC Name

3-hydroxy-5-[methoxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one

Traditional Name

3-hydroxy-5-[methoxy(phenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one

CAS Registry Number

Not Available

SMILES

COC(C1C(C(O)C(=O)N1C)C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H21NO3/c1-20-16(18(23-2)14-11-7-4-8-12-14)15(17(21)19(20)22)13-9-5-3-6-10-13/h3-12,15-18,21H,1-2H3

InChI Key

MNNOPIIJDXUZST-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Clausena lansium	Plant	KNApSAcK

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
Benzylether
Monocyclic benzene moiety
Pyrrolidone
2-pyrrolidone
N-alkylpyrrolidine
Benzenoid
Pyrrole
Tertiary carboxylic acid amide
Secondary alcohol
Carboxamide group
Lactam
Azacycle
Carboxylic acid derivative
Dialkyl ether
Ether
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Alcohol
Organic oxide
Carbonyl group
Organic oxygen compound
Organic nitrogen 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	2.23	ALOGPS
logP	2.11	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.78	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	88.11 m³·mol⁻¹	ChemAxon
Polarizability	33.08 Å³	ChemAxon
Number of Rings	3	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

HMDB0029858

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001080

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

85584195

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Lansimide 3 (NP0086367)

MOL for NP0086367 (Lansimide 3)

3D MOL for NP0086367 (Lansimide 3)

3D SDF for NP0086367 (Lansimide 3)

3D-SDF for NP0086367 (Lansimide 3)

PDB for NP0086367 (Lansimide 3)

3D PDB for NP0086367 (Lansimide 3)

SMILES for NP0086367 (Lansimide 3)

INCHI for NP0086367 (Lansimide 3)

Structure for NP0086367 (Lansimide 3)

3D Structure for NP0086367 (Lansimide 3)