NP-MRD: Showing NP-Card for (2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium (NP0199324)

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Record Information

Version

2.0

Created at

2022-09-04 17:57:10 UTC

Updated at

2022-09-04 17:57:11 UTC

NP-MRD ID

NP0199324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium

Description

Incasine B' belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid. (2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium is found in Incarvillea sinensis. Based on a literature review very few articles have been published on Incasine B'.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042219572D          

 35 38  0  0  1  0            999 V2000
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M  CHG  1  16   1
M  END

     RDKit          3D

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  3 36  1  0
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M  CHG  1  16   1
M  END


  Mrv1652309042219572D          

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 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 32 33  1  4  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 11 35  1  0  0  0  0
M  CHG  1  16   1
M  END
> <DATABASE_ID>
NP0199324

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=NCCCN(CCCC[N+]2=CN(CCC2)[C@@H](C1)C1=CC=CC=C1)C(=O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H36N4O2/c34-28-23-27(26-13-5-2-6-14-26)33-22-10-19-31(24-33)18-7-8-20-32(21-9-17-30-28)29(35)16-15-25-11-3-1-4-12-25/h1-6,11-16,24,27H,7-10,17-23H2/p+1/b16-15+/t27-/m0/s1

> <INCHI_KEY>
SEUKOEKHOYPBJF-VHRAYMLOSA-O

> <FORMULA>
C29H37N4O2

> <MOLECULAR_WEIGHT>
473.64

> <EXACT_MASS>
473.291102868

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.71792398162504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-4-hydroxy-2-phenyl-9-[(2E)-3-phenylprop-2-enoyl]-1,5,9,14lambda5-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium

> <JCHEM_LOGP>
-2.712541948383128

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.415394228019875

> <JCHEM_PKA_STRONGEST_BASIC>
15.000000000253074

> <JCHEM_POLAR_SURFACE_AREA>
59.150000000000006

> <JCHEM_REFRACTIVITY>
153.54890000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-4-hydroxy-2-phenyl-9-[(2E)-3-phenylprop-2-enoyl]-1,5,9,14lambda5-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0      14.337   0.508   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      12.886  -0.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.610  -1.525   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.784  -2.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.507  -4.037   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.681  -5.034   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.405  -6.549   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.954  -7.067   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.781  -6.070   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.057  -4.555   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      11.713   0.986   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      10.138   0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.378  -0.954   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.869  -0.645   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.697   0.886   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.487   2.058   0.000  0.00  0.00           N+1
HETATM   17  C   UNK     0       6.796   3.566   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       5.644   4.589   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       4.183   4.102   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.874   2.594   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.025   1.571   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.953   6.097   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.801   7.119   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.340   6.633   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.188   7.655   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.498   9.164   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.959   9.650   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.111   8.628   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.414   6.584   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.566   5.562   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.257   4.053   0.000  0.00  0.00           O+0
HETATM   32  N   UNK     0      10.027   6.048   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      11.179   5.026   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.870   3.517   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.022   2.495   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    2   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   18   23   29                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   22   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   11                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₇N₄O₂

Average Mass

473.6400 Da

Monoisotopic Mass

473.29110 Da

IUPAC Name

(2S)-4-hydroxy-2-phenyl-9-[(2E)-3-phenylprop-2-enoyl]-1,5,9,14lambda5-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium

Traditional Name

(2S)-4-hydroxy-2-phenyl-9-[(2E)-3-phenylprop-2-enoyl]-1,5,9,14lambda5-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium

CAS Registry Number

Not Available

SMILES

OC1=NCCCN(CCCC[N+]2=CN(CCC2)[C@@H](C1)C1=CC=CC=C1)C(=O)\C=C\C1=CC=CC=C1

InChI Identifier

InChI=1S/C29H36N4O2/c34-28-23-27(26-13-5-2-6-14-26)33-22-10-19-31(24-33)18-7-8-20-32(21-9-17-30-28)29(35)16-15-25-11-3-1-4-12-25/h1-6,11-16,24,27H,7-10,17-23H2/p+1/b16-15+/t27-/m0/s1

InChI Key

SEUKOEKHOYPBJF-VHRAYMLOSA-O

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

Species Name	Source	Reference
Incarvillea sinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
Styrene
Monocyclic benzene moiety
Hydropyrimidine
1,4,5,6-tetrahydropyrimidine
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Secondary carboxylic acid amide
Amidine
Carboxylic acid amidine
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Carboximidamide
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organic cation
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	-2.7	ChemAxon
pKa (Strongest Acidic)	-3.4	ChemAxon
pKa (Strongest Basic)	15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	153.55 m³·mol⁻¹	ChemAxon
Polarizability	53.72 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

15815845

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium (NP0199324)

MOL for NP0199324 ((2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium)

3D MOL for NP0199324 ((2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium)

3D SDF for NP0199324 ((2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium)

3D-SDF for NP0199324 ((2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium)

PDB for NP0199324 ((2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium)

3D PDB for NP0199324 ((2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium)

SMILES for NP0199324 ((2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium)

INCHI for NP0199324 ((2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium)

Structure for NP0199324 ((2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium)

3D Structure for NP0199324 ((2s)-4-hydroxy-2-phenyl-9-[(2e)-3-phenylprop-2-enoyl]-1,5,9,14λ⁵-tetraazabicyclo[12.3.1]octadeca-4,14(18)-dien-14-ylium)