NP-MRD: Showing NP-Card for 2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate (NP0316901)

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Record Information

Version

2.0

Created at

2022-09-11 16:24:02 UTC

Updated at

2022-09-11 16:24:02 UTC

NP-MRD ID

NP0316901

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate

Description

2,18-Dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]Henicosa-3(8),4,6-triene-2,18-dicarboxylate belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond. 2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate is found in Kopsia pauciflora. 2,18-Dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]Henicosa-3(8),4,6-triene-2,18-dicarboxylate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161505482D          

 36 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161505482D          

 36 41  0  0  0  0            999 V2000
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 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
  5 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 23 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 23 34  1  0  0  0  0
 16 34  1  0  0  0  0
 19 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  3  0  0  0  0
M  END
> <DATABASE_ID>
NP0316901

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=C(OC)C(OC)=CC=C2C23CCN4CCCC5(CCC12C(O)(C5)C(=O)OC)C34C#N

> <INCHI_IDENTIFIER>
InChI=1S/C26H31N3O7/c1-33-17-7-6-16-18(19(17)34-2)29(21(31)36-4)25-10-9-22(14-24(25,32)20(30)35-3)8-5-12-28-13-11-23(16,25)26(22,28)15-27/h6-7,32H,5,8-14H2,1-4H3

> <INCHI_KEY>
HLKPNUPXCCOXTL-UHFFFAOYSA-N

> <FORMULA>
C26H31N3O7

> <MOLECULAR_WEIGHT>
497.548

> <EXACT_MASS>
497.21620035

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.50197782355901

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate

> <ALOGPS_LOGP>
1.40

> <JCHEM_LOGP>
1.2361899899999984

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.60331652034116

> <JCHEM_PKA_STRONGEST_BASIC>
5.576475328236721

> <JCHEM_POLAR_SURFACE_AREA>
121.56

> <JCHEM_REFRACTIVITY>
125.87529999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      14.883   4.457   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      13.614   5.328   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      12.208   4.657   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.167   6.262   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0      11.172   3.311   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      11.906   1.934   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.350   1.400   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.893   1.894   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      16.482   1.898   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.610  -0.118   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      15.041  -0.987   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      15.357  -2.557   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.425  -1.102   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.981  -0.568   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.721   0.950   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.108   1.124   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.213  -0.481   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.235  -1.690   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       7.001  -0.682   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       5.467  -1.110   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.239  -0.108   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.386   1.470   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.916   1.999   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.153   2.609   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.474   2.186   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.665   2.817   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.672   3.687   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.113   5.303   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.562   3.610   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.262   5.489   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.996   7.106   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       7.145   6.656   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.650   6.290   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.318   0.927   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.619   1.842   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       7.624   3.362   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15   17   26   34                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   34                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   29   34                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    5   16   27                                             
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27   23                                                       
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
CONECT   34   23   16   19   35                                             
CONECT   35   34   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Value	Source
2,18-Dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1,.0,.0,.0,]henicosa-3(8),4,6-triene-2,18-dicarboxylic acid	Generator
2,18-Dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylic acid	Generator

Chemical Formula

C₂₆H₃₁N₃O₇

Average Mass

497.5480 Da

Monoisotopic Mass

497.21620 Da

IUPAC Name

2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate

Traditional Name

2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=C(OC)C(OC)=CC=C2C23CCN4CCCC5(CCC12C(O)(C5)C(=O)OC)C34C#N

InChI Identifier

InChI=1S/C26H31N3O7/c1-33-17-7-6-16-18(19(17)34-2)29(21(31)36-4)25-10-9-22(14-24(25,32)20(30)35-3)8-5-12-28-13-11-23(16,25)26(22,28)15-27/h6-7,32H,5,8-14H2,1-4H3

InChI Key

HLKPNUPXCCOXTL-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

Species Name	Source	Reference
Kopsia pauciflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidofractine alkaloids. These are alkaloids with a structure that is based on the hexacyclic aspidofractine core. These compounds are related to the Aspidosperma group by formation of a C-2 to C-18 bond.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidofractine alkaloids

Sub Class

Not Available

Direct Parent

Aspidofractine alkaloids

Alternative Parents

Substituents

Aspidofractine skeleton
Carbazole
Indolecarboxylic acid derivative
Indolecarboxylic acid
Quinolidine
Azaspirodecane
Indole or derivatives
Indolizidine
Anisole
Aralkylamine
Alkyl aryl ether
Benzenoid
N-alkylpyrrolidine
Piperidine
Pyrrolidine
Methyl ester
Carbamic acid ester
Tertiary alcohol
Cyclic alcohol
Amino acid or derivatives
Alpha-aminonitrile
Carboxylic acid ester
Tertiary aliphatic amine
Carbonic acid derivative
Tertiary amine
Nitrile
Carbonitrile
Carboxylic acid derivative
Ether
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Amine
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organopnictogen 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	1.4	ALOGPS
logP	1.24	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.6	ChemAxon
pKa (Strongest Basic)	5.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	121.56 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	125.88 m³·mol⁻¹	ChemAxon
Polarizability	50.5 Å³	ChemAxon
Number of Rings	6	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

72822298

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate (NP0316901)

MOL for NP0316901 (2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate)

3D MOL for NP0316901 (2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate)

3D SDF for NP0316901 (2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate)

3D-SDF for NP0316901 (2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate)

PDB for NP0316901 (2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate)

3D PDB for NP0316901 (2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate)

SMILES for NP0316901 (2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate)

INCHI for NP0316901 (2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate)

Structure for NP0316901 (2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate)

3D Structure for NP0316901 (2,18-dimethyl 21-cyano-18-hydroxy-4,5-dimethoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3(8),4,6-triene-2,18-dicarboxylate)