NP-MRD: Showing NP-Card for 4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate (NP0243043)

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Record Information

Version

2.0

Created at

2022-09-07 03:30:33 UTC

Updated at

2022-09-07 03:30:34 UTC

NP-MRD ID

NP0243043

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate

Description

4,5-Dimethyl (1R,4R,12S,13R,21R)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]Henicosa-6(11),7,9-triene-4,5-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. 4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate is found in Kopsia arborea. Based on a literature review very few articles have been published on 4,5-dimethyl (1R,4R,12S,13R,21R)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]Henicosa-6(11),7,9-triene-4,5-dicarboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072205302D          

 32 37  0  0  1  0            999 V2000
    5.8809   -3.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6155   -2.2478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8063   -2.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625   -2.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5409   -1.3059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0447   -0.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8640   -0.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3572   -1.2093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1765   -1.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1902    0.2099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6971    0.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8777    0.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5515    0.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7398   -0.2163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9038    0.6446    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1575    0.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5254    0.4831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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 32 17  1  1  0  0  0
 14 32  1  0  0  0  0
M  END

     RDKit          2D

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   -4.5758   -2.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 29 59  1  0
 32 60  1  6
M  END


  Mrv1652309072205302D          

 32 37  0  0  1  0            999 V2000
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    5.6155   -2.2478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8063   -2.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2625   -2.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5409   -1.3059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0243043

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=C(OC)C=CC=C2[C@]23[C@@H]4CN5CCC[C@@](CC[C@@]12C(=O)OC)(CC4=O)[C@H]35

> <INCHI_IDENTIFIER>
InChI=1S/C24H28N2O6/c1-30-17-7-4-6-14-18(17)26(21(29)32-3)23(20(28)31-2)10-9-22-8-5-11-25-13-15(16(27)12-22)24(14,23)19(22)25/h4,6-7,15,19H,5,8-13H2,1-3H3/t15-,19-,22-,23+,24-/m1/s1

> <INCHI_KEY>
MSSNAZSJDGAHLN-AHJYRWHYSA-N

> <FORMULA>
C24H28N2O6

> <MOLECULAR_WEIGHT>
440.496

> <EXACT_MASS>
440.19473663

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
34.336888528792606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5-dimethyl (1R,4R,12S,13R,21R)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1^{1,12}.0^{4,12}.0^{6,11}.0^{15,21}]henicosa-6,8,10-triene-4,5-dicarboxylate

> <JCHEM_LOGP>
1.8658311533333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.861443219677803

> <JCHEM_PKA_STRONGEST_BASIC>
8.035710843867008

> <JCHEM_POLAR_SURFACE_AREA>
85.38

> <JCHEM_REFRACTIVITY>
113.44759999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dimethyl (1R,4R,12S,13R,21R)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1^{1,12}.0^{4,12}.0^{6,11}.0^{15,21}]henicosa-6,8,10-triene-4,5-dicarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      10.978  -5.654   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.482  -4.196   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.972  -3.896   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       7.957  -5.054   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       8.476  -2.438   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       9.417  -1.203   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.946  -1.023   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.867  -2.257   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      13.396  -2.077   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.555   0.392   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.635   1.626   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.105   1.446   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.496   0.032   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.981  -0.404   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.287   1.203   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.894   1.693   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.714   0.902   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       3.140   1.571   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.142   0.405   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.855  -0.941   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.417  -0.324   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.234  -1.960   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.554  -2.830   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.963  -2.027   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.157  -3.555   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.029  -5.089   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.931  -4.487   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.125  -6.014   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.704   1.756   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.293   2.481   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.660   3.977   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.480  -0.343   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   24                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13   15   24   32                                             
CONECT   15   14   16   30                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   32                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   29   32                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    5   14   25                                             
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27                                                            
CONECT   29   21   30                                                       
CONECT   30   29   15   31                                                  
CONECT   31   30                                                            
CONECT   32   21   17   14                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Value	Source
4,5-Dimethyl (1R,4R,12S,13R,21R)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1,.0,.0,.0,]henicosa-6(11),7,9-triene-4,5-dicarboxylic acid	Generator

Chemical Formula

C₂₄H₂₈N₂O₆

Average Mass

440.4960 Da

Monoisotopic Mass

440.19474 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=C(OC)C=CC=C2[C@]23[C@@H]4CN5CCC[C@@](CC[C@@]12C(=O)OC)(CC4=O)[C@H]35

InChI Identifier

InChI=1S/C24H28N2O6/c1-30-17-7-4-6-14-18(17)26(21(29)32-3)23(20(28)31-2)10-9-22-8-5-11-25-13-15(16(27)12-22)24(14,23)19(22)25/h4,6-7,15,19H,5,8-13H2,1-3H3/t15-,19-,22-,23+,24-/m1/s1

InChI Key

MSSNAZSJDGAHLN-AHJYRWHYSA-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 arborea	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
Aspidosperma alkaloid
Alpha-amino acid ester
Carbazole
Indolecarboxylic acid derivative
Indolecarboxylic acid
Alpha-amino acid or derivatives
Quinolidine
Indolizidine
Indole or derivatives
Anisole
Azepane
Aralkylamine
Alkyl aryl ether
Benzenoid
Piperidine
N-alkylpyrrolidine
Pyrrolidine
Carbamic acid ester
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Ketone
Carbonic acid derivative
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organic oxide
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

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

162977273

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate (NP0243043)

MOL for NP0243043 (4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate)

3D MOL for NP0243043 (4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate)

3D SDF for NP0243043 (4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate)

3D-SDF for NP0243043 (4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate)

PDB for NP0243043 (4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate)

3D PDB for NP0243043 (4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate)

SMILES for NP0243043 (4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate)

INCHI for NP0243043 (4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate)

Structure for NP0243043 (4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate)

3D Structure for NP0243043 (4,5-dimethyl (1r,4r,12s,13r,21r)-7-methoxy-20-oxo-5,15-diazahexacyclo[11.5.2.1¹,¹².0⁴,¹².0⁶,¹¹.0¹⁵,²¹]henicosa-6,8,10-triene-4,5-dicarboxylate)