NP-MRD: Showing NP-Card for methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate (NP0255307)

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Record Information

Version

2.0

Created at

2022-09-07 19:45:24 UTC

Updated at

2022-09-07 19:45:24 UTC

NP-MRD ID

NP0255307

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate

Description

Nareline methyl ether belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate is found in Alstonia scholaris. Based on a literature review very few articles have been published on Nareline methyl ether.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072221452D          

 27 32  0  0  1  0            999 V2000
   -0.8624   -1.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3023   -0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0773   -0.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0986   -0.6362    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0029    0.1687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4660    0.8515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1062    1.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1963   -0.0465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4197   -1.0623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449   -2.1119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9547   -2.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8365   -1.9582    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8597   -1.7856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1450   -2.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8749   -2.9441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6172   -3.1938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025   -3.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5718   -1.3596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3894   -2.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0625   -2.6943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445   -2.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5569   -2.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0874   -1.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8055   -0.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9931   -0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4626   -1.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  1  0  0  0
 11 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 19 27  1  0  0  0  0
M  END


  Mrv1652309072221452D          

 27 32  0  0  1  0            999 V2000
   -0.8624   -1.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3023   -0.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5023   -1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0773   -0.6537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0986   -0.6362    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0029    0.1687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4660    0.8515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1062    1.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1963   -0.0465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4197   -1.0623    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5449   -2.1119    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9547   -2.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8365   -1.9582    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8597   -1.7856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1450   -2.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8749   -2.9441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6172   -3.1938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9025   -3.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5718   -1.3596    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3894   -2.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0625   -2.6943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445   -2.2289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5569   -2.3724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0874   -1.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8055   -0.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9931   -0.8217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4626   -1.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  1  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  1  0  0  0
 11 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 19 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255307

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1ON2C3[C@H]1[C@]14[C@@H]([C@@H](C[C@H]2C1=NC1=CC=CC=C41)\C3=C/C)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H22N2O4/c1-4-10-11-9-14-18-21(15(11)19(24)25-2,12-7-5-6-8-13(12)22-18)16-17(10)23(14)27-20(16)26-3/h4-8,11,14-17,20H,9H2,1-3H3/b10-4+/t11-,14-,15-,16+,17?,20-,21-/m0/s1

> <INCHI_KEY>
XAPXZORJNSUNGB-CJOGCNLXSA-N

> <FORMULA>
C21H22N2O4

> <MOLECULAR_WEIGHT>
366.417

> <EXACT_MASS>
366.157957196

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
35.92601574192316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1R,10S,12R,13E,17S,18R,19R)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{14,18}]nonadeca-2,4,6,8-tetraene-19-carboxylate

> <JCHEM_LOGP>
2.4830341786666654

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.985965164722062

> <JCHEM_POLAR_SURFACE_AREA>
60.36

> <JCHEM_REFRACTIVITY>
99.50140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,10S,12R,13E,17S,18R,19R)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{14,18}]nonadeca-2,4,6,8-tetraene-19-carboxylate

> <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      -1.610  -2.965   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.564  -1.834   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.938  -2.174   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.011  -1.220   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.917  -1.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.739   0.315   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.603   1.589   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.932   2.975   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.233  -0.087   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       2.650  -1.983   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.884  -3.942   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.782  -4.912   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.562  -3.655   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.471  -3.333   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.004  -4.778   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.367  -5.496   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.019  -5.962   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.551  -7.407   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.801  -2.538   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.460  -4.020   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       5.717  -5.029   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       6.990  -4.161   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.506  -4.428   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.497  -3.249   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.970  -1.802   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.454  -1.534   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.463  -2.713   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6   19                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12    3   14                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   14    5   20   27                                             
CONECT   20   19   11   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   22   19                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂N₂O₄

Average Mass

366.4170 Da

Monoisotopic Mass

366.15796 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@H]1ON2C3[C@H]1[C@]14[C@@H]([C@@H](C[C@H]2C1=NC1=CC=CC=C41)\C3=C/C)C(=O)OC

InChI Identifier

InChI=1S/C21H22N2O4/c1-4-10-11-9-14-18-21(15(11)19(24)25-2,12-7-5-6-8-13(12)22-18)16-17(10)23(14)27-20(16)26-3/h4-8,11,14-17,20H,9H2,1-3H3/b10-4+/t11-,14-,15-,16+,17?,20-,21-/m0/s1

InChI Key

XAPXZORJNSUNGB-CJOGCNLXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alstonia scholaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Ortho-oxazepine
Piperidine
Benzenoid
Isoxazolidine
Methyl ester
Carboxylic acid ester
Ketimine
N-organohydroxylamine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Oxacycle
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Imine
Organic oxygen compound
Carbonyl group
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

101712320

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate (NP0255307)

MOL for NP0255307 (methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate)

3D MOL for NP0255307 (methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate)

3D SDF for NP0255307 (methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate)

3D-SDF for NP0255307 (methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate)

PDB for NP0255307 (methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate)

3D PDB for NP0255307 (methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate)

SMILES for NP0255307 (methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate)

INCHI for NP0255307 (methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate)

Structure for NP0255307 (methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate)

3D Structure for NP0255307 (methyl (1r,10s,12r,13e,17s,18r,19r)-13-ethylidene-17-methoxy-16-oxa-8,15-diazahexacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹⁴,¹⁸]nonadeca-2,4,6,8-tetraene-19-carboxylate)