NP-MRD: Showing NP-Card for 2,18-dimethyl (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate (NP0190189)

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Record Information

Version

2.0

Created at

2022-09-04 06:48:39 UTC

Updated at

2022-09-04 06:48:39 UTC

NP-MRD ID

NP0190189

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,18-dimethyl (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate

Description

Kopsiloscine E 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 (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate is found in Kopsia singapurensis. Based on a literature review very few articles have been published on kopsiloscine E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042208482D          

 34 39  0  0  1  0            999 V2000
    6.0919    3.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1098    2.6555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9852    1.7739    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3782    1.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1520    0.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2909   -0.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          2D

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M  END


  Mrv1652309042208482D          

 34 39  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0190189

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)N1C2=CC=C(OC)C=C2[C@@]23CCN4CC[C@H](O)[C@@]5(CC[C@]12[C@@](O)([C@H]5O)C(=O)OC)[C@@H]34

> <INCHI_IDENTIFIER>
InChI=1S/C24H30N2O8/c1-32-13-4-5-15-14(12-13)22-9-11-25-10-6-16(27)21(17(22)25)7-8-23(22,26(15)20(30)34-3)24(31,18(21)28)19(29)33-2/h4-5,12,16-18,27-28,31H,6-11H2,1-3H3/t16-,17-,18-,21-,22+,23-,24+/m0/s1

> <INCHI_KEY>
FELVAZDUIFIGTH-HCIKLWIJSA-N

> <FORMULA>
C24H30N2O8

> <MOLECULAR_WEIGHT>
474.51

> <EXACT_MASS>
474.200215934

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
37.32592584746567

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,18-dimethyl (1S,9R,15S,16R,17S,18R,21R)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7-triene-2,18-dicarboxylate

> <JCHEM_LOGP>
-0.5928192883333329

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.845652547725589

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.764125960561593

> <JCHEM_PKA_STRONGEST_BASIC>
8.394388548522342

> <JCHEM_POLAR_SURFACE_AREA>
129.0

> <JCHEM_REFRACTIVITY>
116.9878

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,18-dimethyl (1S,9R,15S,16R,17S,18R,21R)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7-triene-2,18-dicarboxylate

> <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  C   UNK     0      11.372   7.381   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.797   5.952   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.747   4.740   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      13.272   4.957   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  C   UNK     0      13.610  -0.118   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.425  -1.102   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.684  -2.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      14.129  -3.154   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.981  -0.568   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.721   0.950   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.108   1.124   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.213  -0.481   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.235  -1.690   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       7.001  -0.682   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       5.467  -1.110   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.239  -0.108   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.386   1.470   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.175   2.421   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.916   1.999   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.153   2.609   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.474   2.186   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.665   2.817   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.257   3.817   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.458   4.781   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.658   5.236   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.130   5.428   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       8.588   6.464   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.990   7.883   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.562   3.610   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.623   4.830   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.318   0.927   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   25                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13   15   25   34                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   34                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   32   34                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    5   14   26                                             
CONECT   26   25   27   28   32                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30                                                            
CONECT   32   26   22   33                                                  
CONECT   33   32                                                            
CONECT   34   22   17   14                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₀N₂O₈

Average Mass

474.5100 Da

Monoisotopic Mass

474.20022 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)N1C2=CC=C(OC)C=C2[C@@]23CCN4CC[C@H](O)[C@@]5(CC[C@]12[C@@](O)([C@H]5O)C(=O)OC)[C@@H]34

InChI Identifier

InChI=1S/C24H30N2O8/c1-32-13-4-5-15-14(12-13)22-9-11-25-10-6-16(27)21(17(22)25)7-8-23(22,26(15)20(30)34-3)24(31,18(21)28)19(29)33-2/h4-5,12,16-18,27-28,31H,6-11H2,1-3H3/t16-,17-,18-,21-,22+,23-,24+/m0/s1

InChI Key

FELVAZDUIFIGTH-HCIKLWIJSA-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 singapurensis	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
Carbazole
Indolecarboxylic acid derivative
Indolecarboxylic acid
Azaspirodecane
Quinolidine
Indole or derivatives
Indolizidine
Anisole
Alkyl aryl ether
Beta-hydroxy acid
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Hydroxy acid
Piperidine
Pyrrolidine
Methyl ester
Cyclic alcohol
Tertiary alcohol
Carbamic acid ester
Secondary alcohol
Carboxylic acid ester
Amino acid or derivatives
Carbonic acid derivative
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Amine
Organic oxygen compound
Organooxygen compound
Organopnictogen compound
Organonitrogen 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00039578

Chemspider ID

23310942

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44445382

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 (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate (NP0190189)

MOL for NP0190189 (2,18-dimethyl (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

3D MOL for NP0190189 (2,18-dimethyl (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

3D SDF for NP0190189 (2,18-dimethyl (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

3D-SDF for NP0190189 (2,18-dimethyl (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

PDB for NP0190189 (2,18-dimethyl (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

3D PDB for NP0190189 (2,18-dimethyl (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

SMILES for NP0190189 (2,18-dimethyl (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

INCHI for NP0190189 (2,18-dimethyl (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

Structure for NP0190189 (2,18-dimethyl (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)

3D Structure for NP0190189 (2,18-dimethyl (1s,9r,15s,16r,17s,18r,21r)-15,17,18-trihydroxy-6-methoxy-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-2,18-dicarboxylate)