NP-MRD: Showing NP-Card for (1r,9r,16r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylic acid (NP0330797)

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Record Information

Version

2.0

Created at

2022-09-12 16:30:19 UTC

Updated at

2022-09-12 16:30:19 UTC

NP-MRD ID

NP0330797

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,9r,16r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylic acid

Description

Kopsininic acid, also known as kopsininate, 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. Based on a literature review very few articles have been published on Kopsininic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309122218302D          

 24 29  0  0  1  0            999 V2000
    4.2482   -1.1730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4551   -0.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8619   -1.5193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2551   -0.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3476   -0.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041    0.8325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1853    1.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089    1.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7684    2.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    2.2669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526    2.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7743    2.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7153    1.2961    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5675    1.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7089    2.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4835    2.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167    1.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9753    1.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2007    0.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8179    0.1208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0110    0.3879    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3740    0.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6657    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7567    1.4041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
  4 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 10  1  6  0  0  0
  6 24  1  0  0  0  0
M  END


  Mrv1652309122218302D          

 24 29  0  0  1  0            999 V2000
    4.2482   -1.1730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4551   -0.9459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8619   -1.5193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2551   -0.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3476   -0.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0041    0.8325    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1853    1.1181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089    1.9639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7684    2.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    2.2669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2526    2.8046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7743    2.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7153    1.2961    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5675    1.3968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7089    2.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4835    2.4935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167    1.9646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9753    1.1519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2007    0.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8179    0.1208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0110    0.3879    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3740    0.7278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6657    0.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7567    1.4041    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
  4 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
  6 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 10  1  6  0  0  0
  6 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0330797

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1C[C@]23CCCN4CC[C@]5([C@H]24)C2=CC=CC=C2N[C@]15CC3

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2O2/c23-16(24)14-12-18-6-3-10-22-11-9-19(17(18)22)13-4-1-2-5-15(13)21-20(14,19)8-7-18/h1-2,4-5,14,17,21H,3,6-12H2,(H,23,24)/t14?,17-,18+,19+,20+/m0/s1

> <INCHI_KEY>
AZPTZMIACWMVSO-WDRQQNGESA-N

> <FORMULA>
C20H24N2O2

> <MOLECULAR_WEIGHT>
324.424

> <EXACT_MASS>
324.183778021

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.53976022776165

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,9R,16R,21S)-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7-triene-18-carboxylic acid

> <JCHEM_LOGP>
-0.5906658379503543

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.774592212175246

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.162463615829479

> <JCHEM_PKA_STRONGEST_BASIC>
10.374685874247644

> <JCHEM_POLAR_SURFACE_AREA>
52.57

> <JCHEM_REFRACTIVITY>
92.26740000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,16R,21S)-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7-triene-18-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       7.930  -2.190   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.449  -1.766   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.342  -2.836   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.076  -0.272   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.382  -0.059   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.741   1.554   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.213   2.087   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.070   3.666   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.301   4.664   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       4.834   4.232   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.071   5.235   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.045   4.024   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.935   2.419   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.526   2.607   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.790   4.125   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.236   4.655   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.418   3.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.154   2.150   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.708   1.620   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       8.993   0.226   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       7.487   0.724   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.298   1.359   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.976   0.939   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.146   2.621   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   23   24                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   21   24                                             
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    4   13   22                                             
CONECT   22   21   23                                                       
CONECT   23   22    6                                                       
CONECT   24   13   10    6                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

View in JSmol

Synonyms

Value	Source
Kopsininate	Generator

Chemical Formula

C₂₀H₂₄N₂O₂

Average Mass

324.4240 Da

Monoisotopic Mass

324.18378 Da

IUPAC Name

(1R,9R,16R,21S)-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7-triene-18-carboxylic acid

Traditional Name

(1R,9R,16R,21S)-2,12-diazahexacyclo[14.2.2.1^{9,12}.0^{1,9}.0^{3,8}.0^{16,21}]henicosa-3,5,7-triene-18-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1C[C@]23CCCN4CC[C@]5([C@H]24)C2=CC=CC=C2N[C@]15CC3

InChI Identifier

InChI=1S/C20H24N2O2/c23-16(24)14-12-18-6-3-10-22-11-9-19(17(18)22)13-4-1-2-5-15(13)21-20(14,19)8-7-18/h1-2,4-5,14,17,21H,3,6-12H2,(H,23,24)/t14?,17-,18+,19+,20+/m0/s1

InChI Key

AZPTZMIACWMVSO-WDRQQNGESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Quinoline-6-carboxylic acid
Carbazole
Quinolidine
Azaspirodecane
Indolizidine
Dihydroindole
Indole or derivatives
Aralkylamine
Secondary aliphatic/aromatic amine
Benzenoid
N-alkylpyrrolidine
Piperidine
Pyrrolidine
Amino acid
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
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	-0.59	ChemAxon
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	10.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	52.57 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	92.27 m³·mol⁻¹	ChemAxon
Polarizability	35.54 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00024455

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

102597247

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,16r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylic acid (NP0330797)

MOL for NP0330797 ((1r,9r,16r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylic acid)

3D MOL for NP0330797 ((1r,9r,16r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylic acid)

3D SDF for NP0330797 ((1r,9r,16r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylic acid)

3D-SDF for NP0330797 ((1r,9r,16r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylic acid)

PDB for NP0330797 ((1r,9r,16r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylic acid)

3D PDB for NP0330797 ((1r,9r,16r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylic acid)

SMILES for NP0330797 ((1r,9r,16r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylic acid)

INCHI for NP0330797 ((1r,9r,16r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylic acid)

Structure for NP0330797 ((1r,9r,16r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylic acid)

3D Structure for NP0330797 ((1r,9r,16r,21s)-2,12-diazahexacyclo[14.2.2.1⁹,¹².0¹,⁹.0³,⁸.0¹⁶,²¹]henicosa-3,5,7-triene-18-carboxylic acid)