NP-MRD: Showing NP-Card for Piperlactam (NP0069347)

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Record Information

Version

2.0

Created at

2022-04-28 14:42:14 UTC

Updated at

2022-04-28 14:42:14 UTC

NP-MRD ID

NP0069347

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Piperlactam

Description

Piperlactam S belongs to the class of organic compounds known as aristolactams. These are phenanthrenic compounds containing a five-membered lactam ring and a 1,3-dioxolane ring fused to the phenanthrene ring system. Piperlactam S is an extremely weak basic (essentially neutral) compound (based on its pKa). Piperlactam is found in Piper kadsura, Piper puberullum and Piper puberulum. Piperlactam was first documented in 2000 (PMID: 11040054). An organic heterotetracyclic compound that is dibenzoindol-4(5H)-one carrying two methoxy substituents at positions 1 and 5 as well as a hydroxy substituent at position 2 (PMID: 12498929) (PMID: 12567271) (PMID: 12567272) (PMID: 16724856).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 38  0  0  0  0  0  0  0  0999 V2000
   -3.9186   -0.9513   -0.6618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0078   -0.7855    0.4390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6880   -1.0348    0.3433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2638   -2.3859    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2049   -3.3527    0.6480 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0593   -2.7442    0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0526   -1.8171    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6281   -0.5118    0.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6864    0.3177   -0.1882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4102    1.6549   -0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984    2.0960   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1262    3.4600   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4016    3.9423   -0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4441    3.0864    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2582    1.7048    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    1.2289    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7124   -0.1189    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8987   -0.4630   -0.2423 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1003    0.0812   -0.4403 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1454   -0.7903   -0.5128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110   -1.8166   -0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2160   -2.8301   -0.0200 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8380   -0.4132   -0.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741   -1.9872   -0.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4926   -0.4244   -1.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9183   -4.3170    0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589   -3.7817    0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2208    2.3457   -0.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7342    4.1180   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5627    5.0068   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4746    3.4401    0.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1026    1.0992    0.4302 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0646   -0.2855   -0.9384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9370   -1.7146   -1.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4468   -1.0562    0.5448 H   0  0  0  0  0  0  0  0  0  0  0  0
 20 19  1  0
 19 18  1  0
 18 21  1  0
 21 22  2  0
 21  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  9 18  1  0
 16 11  1  0
  6  7  1  0
 17  8  1  0
 20 33  1  0
 20 34  1  0
 20 35  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  5 26  1  0
  6 27  1  0
M  END


  Mrv1533004171520162D          

 22 25  0  0  0  0            999 V2000
   -0.7110   -1.2111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0960   -1.0396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6209    3.2459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1902    2.7360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0186    3.5430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7486    1.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 22  2  0  0  0  0
 13 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069347

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C(=O)C2=C3C1=CC1=CC=CC=C1C3=C(OC)C(O)=C2

> <INCHI_IDENTIFIER>
InChI=1S/C17H13NO4/c1-21-16-13(19)8-11-14-12(18(22-2)17(11)20)7-9-5-3-4-6-10(9)15(14)16/h3-8,19H,1-2H3

> <INCHI_KEY>
LHSDJNRAZBFFLF-UHFFFAOYSA-N

> <FORMULA>
C17H13NO4

> <MOLECULAR_WEIGHT>
295.294

> <EXACT_MASS>
295.084457903

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.362626130626854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-hydroxy-10,15-dimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
2.62477073

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.89105025781062

> <JCHEM_PKA_STRONGEST_BASIC>
-4.54143808998073

> <JCHEM_POLAR_SURFACE_AREA>
59.0

> <JCHEM_REFRACTIVITY>
81.3441

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-10,15-dimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -1.327  -2.261   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.179  -1.941   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       0.655  -0.476   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.790   0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.479   4.553   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.159   6.059   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.088   5.107   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.768   6.614   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.264   2.570   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.454  -0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.120   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   22                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   22                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    3   22                                                  
CONECT   22   21    6   13                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₃NO₄

Average Mass

295.2940 Da

Monoisotopic Mass

295.08446 Da

IUPAC Name

14-hydroxy-10,15-dimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

Traditional Name

14-hydroxy-10,15-dimethoxy-10-azatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-1(15),2,4,6,8,12(16),13-heptaen-11-one

CAS Registry Number

Not Available

SMILES

CON1C(=O)C2=C3C1=CC1=CC=CC=C1C3=C(OC)C(O)=C2

InChI Identifier

InChI=1S/C17H13NO4/c1-21-16-13(19)8-11-14-12(18(22-2)17(11)20)7-9-5-3-4-6-10(9)15(14)16/h3-8,19H,1-2H3

InChI Key

LHSDJNRAZBFFLF-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
Piper kadsura	LOTUS Database	35616633
Piper puberullum	Plant	KNApSAcK
Piper puberulum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aristolactams. These are phenanthrenic compounds containing a five-membered lactam ring and a 1,3-dioxolane ring fused to the phenanthrene ring system.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aristolactams

Sub Class

Not Available

Direct Parent

Aristolactams

Alternative Parents

Substituents

Aristolactam
Phenanthrol
Phenanthrene
2-naphthol
Naphthalene
Isoindolone
Indole or derivatives
Isoindole or derivatives
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Carboxylic acid derivative
Ether
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	3.43	ALOGPS
logP	2.62	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.89	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	81.34 m³·mol⁻¹	ChemAxon
Polarizability	30.36 Å³	ChemAxon
Number of Rings	4	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

622222

PDB ID

Not Available

ChEBI ID

132657

Good Scents ID

Not Available

References

General References

Kuo YC, Yang NS, Chou CJ, Lin LC, Tsai WJ: Regulation of cell proliferation, gene expression, production of cytokines, and cell cycle progression in primary human T lymphocytes by piperlactam S isolated from Piper kadsura. Mol Pharmacol. 2000 Nov;58(5):1057-66. doi: 10.1124/mol.58.5.1057. [PubMed:11040054 ]
Chiou WF, Yau-Chik Shum A, Peng CH, Chen CF, Chou CJ: Piperlactam S suppresses macrophage migration by impeding F-actin polymerization and filopodia extension. Eur J Pharmacol. 2003 Jan 1;458(1-2):217-25. doi: 10.1016/s0014-2999(02)02733-4. [PubMed:12498929 ]
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Showing NP-Card for Piperlactam (NP0069347)

MOL for NP0069347 (Piperlactam)

3D MOL for NP0069347 (Piperlactam)

3D SDF for NP0069347 (Piperlactam)

3D-SDF for NP0069347 (Piperlactam)

PDB for NP0069347 (Piperlactam)

3D PDB for NP0069347 (Piperlactam)

SMILES for NP0069347 (Piperlactam)

INCHI for NP0069347 (Piperlactam)

Structure for NP0069347 (Piperlactam)

3D Structure for NP0069347 (Piperlactam)