NP-MRD: Showing NP-Card for plakinamine b (NP0264017)

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Record Information

Version

2.0

Created at

2022-09-08 07:24:25 UTC

Updated at

2022-09-08 07:24:25 UTC

NP-MRD ID

NP0264017

Secondary Accession Numbers

None

Natural Product Identification

Common Name

plakinamine b

Description

Plakinamine B belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. plakinamine b was first documented in 2007 (PMID: 17610922). Based on a literature review very few articles have been published on Plakinamine B (PMID: 23570516).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082209242D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309082209242D          

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 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 25 32  1  0  0  0  0
  8 33  1  0  0  0  0
  3 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0264017

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN[C@@H]1CC[C@@]2(C)[C@@H](CC=C3[C@@H]4CC[C@H]([C@H](C)\C=C\C5=C(C)CN(C)CC5)[C@@]4(C)CC[C@H]23)C1

> <INCHI_IDENTIFIER>
InChI=1S/C31H50N2/c1-21(7-8-23-15-18-33(6)20-22(23)2)27-11-12-28-26-10-9-24-19-25(32-5)13-16-30(24,3)29(26)14-17-31(27,28)4/h7-8,10,21,24-25,27-29,32H,9,11-20H2,1-6H3/b8-7+/t21-,24+,25-,27-,28+,29+,30+,31-/m1/s1

> <INCHI_KEY>
WYVDKLLQGBHWHH-JHMJTLKLSA-N

> <FORMULA>
C31H50N2

> <MOLECULAR_WEIGHT>
450.755

> <EXACT_MASS>
450.397399618

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
57.988572921995114

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,5R,7S,11R,14R,15R)-14-[(2R,3E)-4-(1,5-dimethyl-1,2,3,6-tetrahydropyridin-4-yl)but-3-en-2-yl]-N,2,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-amine

> <JCHEM_LOGP>
5.868890256

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_BASIC>
10.712366667910839

> <JCHEM_POLAR_SURFACE_AREA>
15.27

> <JCHEM_REFRACTIVITY>
145.06709999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,5R,7S,11R,14R,15R)-14-[(2R,3E)-4-(1,3-dimethyl-5,6-dihydro-2H-pyridin-4-yl)but-3-en-2-yl]-N,2,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-amine

> <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      14.081   2.761   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      13.558   1.312   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.558  -2.907   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.452  -1.269   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.493  -2.485   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.018  -2.275   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.963  -3.490   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.383  -4.917   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.489  -3.280   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      -5.069  -1.853   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -6.595  -1.643   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.124  -0.637   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.599  -0.848   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   33                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   12                                             
CONECT    7    6                                                            
CONECT    8    6    9   33                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   20                                             
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   25                                                       
CONECT   33    8    3                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₅₀N₂

Average Mass

450.7550 Da

Monoisotopic Mass

450.39740 Da

IUPAC Name

(1R,2S,5R,7S,11R,14R,15R)-14-[(2R,3E)-4-(1,5-dimethyl-1,2,3,6-tetrahydropyridin-4-yl)but-3-en-2-yl]-N,2,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-amine

Traditional Name

(1R,2S,5R,7S,11R,14R,15R)-14-[(2R,3E)-4-(1,3-dimethyl-5,6-dihydro-2H-pyridin-4-yl)but-3-en-2-yl]-N,2,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-amine

CAS Registry Number

Not Available

SMILES

CN[C@@H]1CC[C@@]2(C)[C@@H](CC=C3[C@@H]4CC[C@H]([C@H](C)\C=C\C5=C(C)CN(C)CC5)[C@@]4(C)CC[C@H]23)C1

InChI Identifier

InChI=1S/C31H50N2/c1-21(7-8-23-15-18-33(6)20-22(23)2)27-11-12-28-26-10-9-24-19-25(32-5)13-16-30(24,3)29(26)14-17-31(27,28)4/h7-8,10,21,24-25,27-29,32H,9,11-20H2,1-6H3/b8-7+/t21-,24+,25-,27-,28+,29+,30+,31-/m1/s1

InChI Key

WYVDKLLQGBHWHH-JHMJTLKLSA-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 triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Cholestane-skeleton
Delta-7-steroid
Steroid
Hydropyridine
Tertiary amine
Tertiary aliphatic amine
Secondary amine
Secondary aliphatic amine
Azacycle
Organoheterocyclic compound
Amine
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

triterpenoid (CHEBI:80785 )

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	5.87	ChemAxon
pKa (Strongest Basic)	10.71	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	15.27 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	145.07 m³·mol⁻¹	ChemAxon
Polarizability	57.99 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

10243265

KEGG Compound ID

C16895

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21606896

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Langjae R, Bussarawit S, Yuenyongsawad S, Ingkaninan K, Plubrukarn A: Acetylcholinesterase-inhibiting steroidal alkaloid from the sponge Corticium sp. Steroids. 2007 Sep;72(9-10):682-5. doi: 10.1016/j.steroids.2007.05.005. Epub 2007 May 31. [PubMed:17610922 ]
Khan I, Samad A, Khan AZ, Habtemariam S, Badshah A, Abdullah SM, Ullah N, Khan A, Zia-Ul-Haq M: Molecular interactions of 4-acetoxy-plakinamine B with peripheral anionic and other catalytic subsites of the aromatic gorge of acetylcholinesterase: computational and structural insights. Pharm Biol. 2013 Jun;51(6):722-7. doi: 10.3109/13880209.2013.764329. Epub 2013 Apr 9. [PubMed:23570516 ]
LOTUS database [Link]

Showing NP-Card for plakinamine b (NP0264017)

MOL for NP0264017 (plakinamine b)

3D MOL for NP0264017 (plakinamine b)

3D SDF for NP0264017 (plakinamine b)

3D-SDF for NP0264017 (plakinamine b)

PDB for NP0264017 (plakinamine b)

3D PDB for NP0264017 (plakinamine b)

SMILES for NP0264017 (plakinamine b)

INCHI for NP0264017 (plakinamine b)

Structure for NP0264017 (plakinamine b)

3D Structure for NP0264017 (plakinamine b)