NP-MRD: Showing NP-Card for methyl (14e)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate (NP0257215)

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Record Information

Version

2.0

Created at

2022-09-07 22:16:35 UTC

Updated at

2022-09-07 22:16:35 UTC

NP-MRD ID

NP0257215

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (14e)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate

Description

Methyl (14E)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]Nonadeca-3,5,7-triene-19-carboxylate belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group. Methyl (14E)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]Nonadeca-3,5,7-triene-19-carboxylate is a strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231520102D          

 35 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004231520102D          

 35 40  0  0  0  0            999 V2000
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 28 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  2  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 13 34  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  0  0  0  0
 19 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0257215

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1(COC(C)=O)C2CC3N(C\C2=C\C)C2CC11C4=CC(OC)=C(OC)C=C4N(C)C31O2

> <INCHI_IDENTIFIER>
InChI=1S/C26H32N2O7/c1-7-15-12-28-21-9-16(15)24(23(30)33-6,13-34-14(2)29)25-11-22(28)35-26(21,25)27(3)18-10-20(32-5)19(31-4)8-17(18)25/h7-8,10,16,21-22H,9,11-13H2,1-6H3/b15-7-

> <INCHI_KEY>
HNGUEAQTTKIQOG-CHHVJCJISA-N

> <FORMULA>
C26H32N2O7

> <MOLECULAR_WEIGHT>
484.549

> <EXACT_MASS>
484.220951378

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.193670004102856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (14E)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
2.3885627536666654

> <ALOGPS_LOGS>
-3.08

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.766624245870913

> <JCHEM_POLAR_SURFACE_AREA>
86.77000000000001

> <JCHEM_REFRACTIVITY>
126.8869

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (14E)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       3.448  -3.855   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.613  -2.324   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.370  -1.416   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.961  -2.039   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.534   0.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.999  -0.361   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.318  -1.868   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.783  -2.344   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.928  -1.314   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.102  -3.851   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.856  -0.053   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.046   1.071   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.074   2.578   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.004   3.014   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -1.325   1.990   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.799   0.421   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.863  -0.692   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.432  -2.170   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.931   2.365   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.813   2.771   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.357   1.545   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.911   1.393   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.775   0.118   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.311   0.229   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.175  -1.046   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       9.711  -0.935   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.983   1.614   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.519   1.725   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.191   3.111   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.119   2.889   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.583   2.778   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       4.472   3.925   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0       4.789   5.432   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.883   3.276   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.927   4.152   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11   21                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    5   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   34                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   14   20   35                                                  
CONECT   20   19   21                                                       
CONECT   21   20    5   22   34                                             
CONECT   22   21   23   31                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31                                                       
CONECT   31   30   22   32                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   13   21   35                                             
CONECT   35   34   19                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Value	Source
Methyl (14E)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1,.0,.0,.0,]nonadeca-3,5,7-triene-19-carboxylic acid	Generator
Methyl (14E)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylic acid	Generator

Chemical Formula

C₂₆H₃₂N₂O₇

Average Mass

484.5490 Da

Monoisotopic Mass

484.22095 Da

IUPAC Name

methyl (14E)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate

Traditional Name

methyl (14E)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1(COC(C)=O)C2CC3N(C\C2=C\C)C2CC11C4=CC(OC)=C(OC)C=C4N(C)C31O2

InChI Identifier

InChI=1S/C26H32N2O7/c1-7-15-12-28-21-9-16(15)24(23(30)33-6,13-34-14(2)29)25-11-22(28)35-26(21,25)27(3)18-10-20(32-5)19(31-4)8-17(18)25/h7-8,10,16,21-22H,9,11-13H2,1-6H3/b15-7-

InChI Key

HNGUEAQTTKIQOG-CHHVJCJISA-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 corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Corynanthean-type alkaloids

Sub Class

Not Available

Direct Parent

Corynanthean-type alkaloids

Alternative Parents

Substituents

Corynanthean skeleton
Pyridoindole
Carbazole
Beta-carboline
Quinolizidine
Indole or derivatives
Dialkylarylamine
Anisole
Alkyl aryl ether
Benzenoid
Piperidine
Dicarboxylic acid or derivatives
Methyl ester
Tetrahydrofuran
Oxazolidine
Hemiaminal
Carboxylic acid ester
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	2.35	ALOGPS
logP	2.39	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	4.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	86.77 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.89 m³·mol⁻¹	ChemAxon
Polarizability	50.19 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	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (14e)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate (NP0257215)

MOL for NP0257215 (methyl (14e)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D MOL for NP0257215 (methyl (14e)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D SDF for NP0257215 (methyl (14e)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D-SDF for NP0257215 (methyl (14e)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

PDB for NP0257215 (methyl (14e)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D PDB for NP0257215 (methyl (14e)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

SMILES for NP0257215 (methyl (14e)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

INCHI for NP0257215 (methyl (14e)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

Structure for NP0257215 (methyl (14e)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)

3D Structure for NP0257215 (methyl (14e)-19-[(acetyloxy)methyl]-14-ethylidene-5,6-dimethoxy-2-methyl-18-oxa-2,12-diazahexacyclo[9.6.1.1⁹,¹⁵.0¹,⁹.0³,⁸.0¹²,¹⁷]nonadeca-3,5,7-triene-19-carboxylate)