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Showing NP-Card for Isosegoline A (NP0050379)

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Record Information
Version2.0
Created at2022-04-27 20:56:30 UTC
Updated at2022-04-27 20:56:30 UTC
NP-MRD IDNP0050379
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsosegoline A
Description117694-97-0 Belongs to the class of organic compounds known as pyrido[2,3,4-kl]acridines. These are organic heterocyclic compounds with a structure based on the pyrido[2,3,4-kl]acridine skeleton. Isosegoline A is found in Eudistoma sp. Based on a literature review very few articles have been published on 117694-97-0.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0050379 (Isosegoline A)


  Mrv1652304272222562D          

 29 34  0  0  1  0            999 V2000
    0.3492   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1613   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4416    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9948   -0.3634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5266    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1539    1.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901    1.4789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0022    1.6241    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5340    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2537    0.2174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9050   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8782   -1.1135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879    0.1741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649    1.6179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8939    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385    2.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067    3.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4054    3.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6857    2.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0689   -1.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7433   -1.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 22  1  1  0  0  0
 14 23  1  1  0  0  0
 12 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 11 27  2  0  0  0  0
  1 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
Download

3D MOL for NP0050379 (Isosegoline A)

Download
3D SDF for NP0050379 (Isosegoline A)

  Mrv1652304272222562D          

 29 34  0  0  1  0            999 V2000
    0.3492   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1613   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4416    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0976    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9948   -0.3634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5266    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1539    1.9643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6582    2.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1901    1.4789    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0022    1.6241    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5340    0.9934    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2537    0.2174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9050   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8782   -1.1135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5879    0.1741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3586    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8649    1.6179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8939    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2825    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9385    2.8855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4067    3.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4054    3.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6857    2.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0689   -1.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7433   -1.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 22  1  1  0  0  0
 14 23  1  1  0  0  0
 12 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 11 27  2  0  0  0  0
  1 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050379

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C3N([C@@H](C)[C@@]4(C)[C@@H]2C(=O)NC4=O)C2=CC=CC=C2C2=C3C1=NC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C23H19N3O3/c1-11-23(2)18(21(27)25-22(23)28)14-10-16(29-3)19-17-13(8-9-24-19)12-6-4-5-7-15(12)26(11)20(14)17/h4-11,18H,1-3H3,(H,25,27,28)/t11-,18-,23-/m0/s1

> <INCHI_KEY>
HSCRWFYMNNKDLC-ZIKCNTICSA-N

> <FORMULA>
C23H19N3O3

> <MOLECULAR_WEIGHT>
385.423

> <EXACT_MASS>
385.142641484

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
40.45185924166536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(16R,20R,21S)-13-methoxy-20,21-dimethyl-1,11,18-triazahexacyclo[10.9.2.0^{2,7}.0^{8,23}.0^{15,22}.0^{16,20}]tricosa-2,4,6,8(23),9,11,13,15(22)-octaene-17,19-dione

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
2.7742649836666664

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.32384524353184

> <JCHEM_PKA_STRONGEST_BASIC>
2.7492183386396607

> <JCHEM_POLAR_SURFACE_AREA>
71.53

> <JCHEM_REFRACTIVITY>
106.80420000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(16R,20R,21S)-13-methoxy-20,21-dimethyl-1,11,18-triazahexacyclo[10.9.2.0^{2,7}.0^{8,23}.0^{15,22}.0^{16,20}]tricosa-2,4,6,8(23),9,11,13,15(22)-octaene-17,19-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0050379 (Isosegoline A)
Download
PDB for NP0050379 (Isosegoline A)
HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0       0.652  -1.585   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.168  -1.314   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.691   0.135   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.698   1.312   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.182   1.041   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.341  -0.407   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.857  -0.678   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -2.850   0.499   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.326   1.947   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.810   2.218   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.287   3.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.229   3.938   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.221   2.761   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       3.737   3.032   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.730   1.854   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.207   0.406   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.423  -0.539   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.373  -2.078   0.000  0.00  0.00           O+0
HETATM   19  N   UNK     0       6.697   0.325   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       6.269   1.804   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.215   3.020   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.402   3.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.261   4.480   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.752   5.386   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.759   6.564   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.757   6.292   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.280   4.844   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.129  -3.033   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.387  -3.304   0.000  0.00  0.00           C+0
CONECT    1    2    6   28                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    5   11                                                  
CONECT   11   10   12   27                                                  
CONECT   12   11   13   24                                                  
CONECT   13   12    4   14                                                  
CONECT   14   13   15   23                                                  
CONECT   15   14   16   20   22                                             
CONECT   16   15    3   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20                                                            
CONECT   22   15                                                            
CONECT   23   14                                                            
CONECT   24   12   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   11                                                       
CONECT   28    1   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   68    0
END

Download
3D PDB for NP0050379 (Isosegoline A)
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SMILES for NP0050379 (Isosegoline A)
COC1=CC2=C3N([C@@H](C)[C@@]4(C)[C@@H]2C(=O)NC4=O)C2=CC=CC=C2C2=C3C1=NC=C2
Download
INCHI for NP0050379 (Isosegoline A)
InChI=1S/C23H19N3O3/c1-11-23(2)18(21(27)25-22(23)28)14-10-16(29-3)19-17-13(8-9-24-19)12-6-4-5-7-15(12)26(11)20(14)17/h4-11,18H,1-3H3,(H,25,27,28)/t11-,18-,23-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC23H19N3O3
Average Mass385.4230 Da
Monoisotopic Mass385.14264 Da
IUPAC Name(16R,20R,21S)-13-methoxy-20,21-dimethyl-1,11,18-triazahexacyclo[10.9.2.0^{2,7}.0^{8,23}.0^{15,22}.0^{16,20}]tricosa-2,4,6,8(23),9,11,13,15(22)-octaene-17,19-dione
Traditional Name(16R,20R,21S)-13-methoxy-20,21-dimethyl-1,11,18-triazahexacyclo[10.9.2.0^{2,7}.0^{8,23}.0^{15,22}.0^{16,20}]tricosa-2,4,6,8(23),9,11,13,15(22)-octaene-17,19-dione
CAS Registry NumberNot Available
SMILES
COC1=CC2=C3N([C@@H](C)[C@@]4(C)[C@@H]2C(=O)NC4=O)C2=CC=CC=C2C2=C3C1=NC=C2
InChI Identifier
InChI=1S/C23H19N3O3/c1-11-23(2)18(21(27)25-22(23)28)14-10-16(29-3)19-17-13(8-9-24-19)12-6-4-5-7-15(12)26(11)20(14)17/h4-11,18H,1-3H3,(H,25,27,28)/t11-,18-,23-/m0/s1
InChI KeyHSCRWFYMNNKDLC-ZIKCNTICSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Eudistoma sp.Animalia
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrido[2,3,4-kl]acridines. These are organic heterocyclic compounds with a structure based on the pyrido[2,3,4-kl]acridine skeleton.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassQuinolines and derivatives  
Sub ClassBenzoquinolines  
Direct ParentPyrido[2,3,4-kl]acridines  
Alternative Parents
Substituents
  • Pyrido[2,3,4-kl]acridine
    • 

  • 1,7-phenanthroline
    • 

  • Naphthyridine
    • 

  • Anisole
    • 

  • Phenol ether
    • 

  • Alkyl aryl ether
    • 

  • Pyridine
    • 

  • Pyrrolidone
    • 

  • 2-pyrrolidone
    • 

  • Benzenoid
    • 

  • Pyrrolidine
    • 

  • Carboxylic acid imide
    • 

  • Heteroaromatic compound
    • 

  • Dicarboximide
    • 

  • Carboxylic acid imide, n-unsubstituted
    • 

  • Lactam
    • 

  • Azacycle
    • 

  • Carboxylic acid derivative
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxide
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.24ALOGPS
logP2.77ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)10.32ChemAxon
pKa (Strongest Basic)2.75ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity106.8 m³·mol⁻¹ChemAxon
Polarizability40.45 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000522  
Chemspider ID10275445  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14447875  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available