NP-MRD: Showing NP-Card for (1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene (NP0256427)

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Record Information

Version

2.0

Created at

2022-09-07 21:15:11 UTC

Updated at

2022-09-07 21:15:12 UTC

NP-MRD ID

NP0256427

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene

Description

1-Methylaspidospermidine belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids. (1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene is found in Aspidosperma quebracho-blanco. Based on a literature review very few articles have been published on 1-Methylaspidospermidine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072223152D          

 22 26  0  0  1  0            999 V2000
    0.1477    0.2147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9183    0.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5589   -0.0103    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7883   -0.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -1.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695   -1.3449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0384   -1.5684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885   -0.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700   -0.2353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7047   -0.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9173   -1.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7140   -1.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2980   -1.0394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0853   -0.2423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2886   -0.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9149    0.7076    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2902    1.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0999    0.5794    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4593    1.0993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6888    0.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1995   -0.5302    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 19 17  1  1  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 10 22  1  0  0  0  0
 22  7  1  6  0  0  0
  3 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256427

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12CCCN3CC[C@@]4([C@@H](CC1)N(C)C1=CC=CC=C41)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C20H28N2/c1-3-19-10-6-13-22-14-12-20(18(19)22)15-7-4-5-8-16(15)21(2)17(20)9-11-19/h4-5,7-8,17-18H,3,6,9-14H2,1-2H3/t17-,18-,19-,20-/m1/s1

> <INCHI_KEY>
SNPQKSKEMHGDOU-UAFMIMERSA-N

> <FORMULA>
C20H28N2

> <MOLECULAR_WEIGHT>
296.458

> <EXACT_MASS>
296.22524891

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
35.21349706307777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9R,12R,19R)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6-triene

> <JCHEM_LOGP>
3.9470727469999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.76814389269053

> <JCHEM_POLAR_SURFACE_AREA>
6.48

> <JCHEM_REFRACTIVITY>
92.25829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,12R,19R)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6-triene

> <JCHEM_VEBER_RULE>
1

$$$$

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       0.276   0.401   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.714   0.951   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.910  -0.019   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.472  -0.570   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.229  -2.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.425  -3.061   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.863  -2.510   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       5.672  -2.928   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.512  -1.637   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.544  -0.439   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.915  -1.140   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.312  -2.628   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.799  -3.028   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.890  -1.940   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.493  -0.452   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.005  -0.052   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       7.308   1.321   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       8.008   2.692   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.786   1.082   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.591   2.052   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.152   1.502   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.106  -0.990   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21   22                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   22                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19   22                                             
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    3                                                       
CONECT   22   10    7    3                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈N₂

Average Mass

296.4580 Da

Monoisotopic Mass

296.22525 Da

IUPAC Name

(1R,9R,12R,19R)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6-triene

Traditional Name

(1R,9R,12R,19R)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6-triene

CAS Registry Number

Not Available

SMILES

CC[C@@]12CCCN3CC[C@@]4([C@@H](CC1)N(C)C1=CC=CC=C41)[C@@H]23

InChI Identifier

InChI=1S/C20H28N2/c1-3-19-10-6-13-22-14-12-20(18(19)22)15-7-4-5-8-16(15)21(2)17(20)9-11-19/h4-5,7-8,17-18H,3,6,9-14H2,1-2H3/t17-,18-,19-,20-/m1/s1

InChI Key

SNPQKSKEMHGDOU-UAFMIMERSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspidosperma quebracho-blanco	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aspidospermatan-type alkaloids. These are tryptophan-derived alkaloids that are derived from the fusion of tryptamine and a terpene unit (generally either 9 or 10 carbons). Aspidospermine and aspidospermidine (along with tabersonine) are the archetypical members of the Aspidosperma alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aspidospermatan-type alkaloids

Sub Class

Not Available

Direct Parent

Aspidospermatan-type alkaloids

Alternative Parents

Substituents

Aspidosperma alkaloid
Plumeran-type alkaloid
Carbazole
Quinolidine
Indole or derivatives
Indolizidine
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Aralkylamine
Benzenoid
N-alkylpyrrolidine
Piperidine
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
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	3.95	ChemAxon
pKa (Strongest Basic)	10.77	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	6.48 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.26 m³·mol⁻¹	ChemAxon
Polarizability	35.21 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

17238162

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16079154

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene (NP0256427)

MOL for NP0256427 ((1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene)

3D MOL for NP0256427 ((1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene)

3D SDF for NP0256427 ((1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene)

3D-SDF for NP0256427 ((1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene)

PDB for NP0256427 ((1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene)

3D PDB for NP0256427 ((1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene)

SMILES for NP0256427 ((1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene)

INCHI for NP0256427 ((1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene)

Structure for NP0256427 ((1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene)

3D Structure for NP0256427 ((1r,9r,12r,19r)-12-ethyl-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]nonadeca-2,4,6-triene)