NP-MRD: Showing NP-Card for Taberdivarine H (NP0140338)

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Record Information

Version

2.0

Created at

2022-06-29 21:26:52 UTC

Updated at

2022-06-29 21:26:52 UTC

NP-MRD ID

NP0140338

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taberdivarine H

Description

Taberdivarine H belongs to the class of organic compounds known as pleiocarpaman alkaloids. These are alkaloids with a structure that is based on the pleiocarpaman skeleton. These alkaloids arise from the cyclization of a corynantheine precursor via C-16 to N-1. Taberdivarine H was first documented in 2019 (PMID: 31081220). Based on a literature review very few articles have been published on Taberdivarine H.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 50  0  0  0  0  0  0  0  0999 V2000
   -2.2635    2.6096    1.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1046    1.1509    1.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7612    0.4141    0.5650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6567   -1.0303    0.8379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1721   -1.8907   -0.1879 N   0  0  2  0  0  4  0  0  0  0  0  0
   -2.2638   -2.6344   -0.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1755   -2.8172    0.2866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2249   -2.6401   -0.3086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5524   -1.1977   -0.1889 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5511   -0.3654   -0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7945    0.8993   -0.4676 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0019    0.9613    0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7984    1.9983    0.5416 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0278    1.7816    1.1247 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4676    0.4787    1.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7058   -0.5964    0.8721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4974   -0.3542    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2454    1.8944   -0.7953 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0555    2.5962   -2.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6761    2.4359   -3.1297 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9325    3.6135   -2.1327 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.5448    1.0978   -0.7196 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5584   -0.0244   -1.7682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6054   -1.0563   -1.2646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3937    3.1040    2.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5343    3.0229    0.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1315    2.9073    2.2338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2880    0.6893    2.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7014   -1.3524    1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673   -1.1788    1.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0379   -3.0566   -1.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4816   -3.4763   -0.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2085   -2.0324   -0.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4570   -3.8796    0.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0497   -2.7877    1.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8858   -3.2721    0.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2184   -2.9283   -1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4158    3.0177    0.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6370    2.6354    1.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4199    0.3193    1.7351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0187   -1.6270    0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2638    2.6366    0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3716    1.7759   -1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6006   -0.4052   -1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2566    0.2981   -2.7514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2232   -1.7346   -2.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 24  1  0
 24 23  1  0
 23 22  1  0
 22 18  1  0
 18 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 18 19  1  0
 19 21  1  0
 19 20  2  0
 22  3  1  0
 17 12  1  0
 24  5  1  0
 17  9  1  0
 11 10  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
 24 46  1  6
 23 44  1  0
 23 45  1  0
 22 43  1  6
 18 42  1  1
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
M  CHG  2   5   1  21  -1
M  END


  Mrv1652306292223262D          

 24 28  0  0  1  0            999 V2000
   -2.0271    2.1312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9819    1.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2459    0.9347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393    0.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4828   -0.4149    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.0147   -1.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8706   -1.1424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2891   -0.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042    0.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0386    0.1666    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2718    0.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5023    1.4722    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4053    1.6583    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0922    1.0549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9284    0.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5782    1.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3433    1.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4586    0.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8089   -0.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0437    0.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    2.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4132    2.6713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0320    3.0377    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -1.0470   -1.0168    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
  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  2  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  1  0  0  0
 12 11  1  6  0  0  0
  3 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  8 20  1  0  0  0  0
 15 20  1  0  0  0  0
 13 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  5 24  1  0  0  0  0
M  CHG  2   5   1  23  -1
M  END
> <DATABASE_ID>
NP0140338

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\C[N+]2(C)CCC3=C4[C@@H]2C[C@@H]1[C@@H](N4C1=CC=CC=C31)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H22N2O2/c1-3-12-11-22(2)9-8-14-13-6-4-5-7-16(13)21-18(14)17(22)10-15(12)19(21)20(23)24/h3-7,15,17,19H,8-11H2,1-2H3/b12-3-/t15-,17-,19+,22?/m0/s1

> <INCHI_KEY>
MBYUFXAXLKULGV-SFQLIIISSA-N

> <FORMULA>
C20H22N2O2

> <MOLECULAR_WEIGHT>
322.408

> <EXACT_MASS>
322.168127956

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.50725834680655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(13E,14S,16S,18R)-13-ethylidene-11-methyl-1,11-diazapentacyclo[12.3.1.0^{2,7}.0^{8,17}.0^{11,16}]octadeca-2,4,6,8(17)-tetraen-11-ium-18-carboxylate

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
-1.436506528805079

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.107195963090058

> <JCHEM_POLAR_SURFACE_AREA>
45.06

> <JCHEM_REFRACTIVITY>
116.14840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(13E,14S,16S,18R)-13-ethylidene-11-methyl-1,11-diazapentacyclo[12.3.1.0^{2,7}.0^{8,17}.0^{11,16}]octadeca-2,4,6,8(17)-tetraen-11-ium-18-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -3.784   3.978   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.700   2.441   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.326   1.745   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.313   0.059   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.901  -0.775   0.000  0.00  0.00           N+1
HETATM    6  C   UNK     0       0.027  -2.139   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.625  -2.132   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.406  -0.732   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.501   0.520   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.072   0.311   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.507   1.694   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.938   2.748   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.757   3.096   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.039   1.969   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.600   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.813   2.489   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.241   1.913   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.456   0.388   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.243  -0.561   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.815   0.015   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.151   4.584   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.638   4.986   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.060   5.670   0.000  0.00  0.00           O-1
HETATM   24  C   UNK     0      -1.954  -1.898   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10   24                                             
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9    5   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11    3   13                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13    9   15                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    8   15                                                  
CONECT   21   13   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    5                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂N₂O₂

Average Mass

322.4080 Da

Monoisotopic Mass

322.16813 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C1\C[N+]2(C)CCC3=C4[C@@H]2C[C@@H]1[C@@H](N4C1=CC=CC=C31)C([O-])=O

InChI Identifier

InChI=1S/C20H22N2O2/c1-3-12-11-22(2)9-8-14-13-6-4-5-7-16(13)21-18(14)17(22)10-15(12)19(21)20(23)24/h3-7,15,17,19H,8-11H2,1-2H3/b12-3-/t15-,17-,19+,22?/m0/s1

InChI Key

MBYUFXAXLKULGV-SFQLIIISSA-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 pleiocarpaman alkaloids. These are alkaloids with a structure that is based on the pleiocarpaman skeleton. These alkaloids arise from the cyclization of a corynantheine precursor via C-16 to N-1.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Pleiocarpaman alkaloids

Sub Class

Not Available

Direct Parent

Pleiocarpaman alkaloids

Alternative Parents

Substituents

Pleiocarpaman skeleton
Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Diazanaphthalene
Alpha-amino acid or derivatives
Naphthyridine
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Piperidine
Benzenoid
Tetraalkylammonium salt
Heteroaromatic compound
Pyrrole
Quaternary ammonium salt
Carboxylic acid salt
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic salt
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen 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

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

95532372

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

134715098

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jarret M, Turpin V, Tap A, Gallard JF, Kouklovsky C, Poupon E, Vincent G, Evanno L: Bioinspired Oxidative Cyclization of the Geissoschizine Skeleton for Enantioselective Total Synthesis of Mavacuran Alkaloids. Angew Chem Int Ed Engl. 2019 Jul 15;58(29):9861-9865. doi: 10.1002/anie.201905227. Epub 2019 Jun 21. [PubMed:31081220 ]

Showing NP-Card for Taberdivarine H (NP0140338)

MOL for NP0140338 (Taberdivarine H)

3D MOL for NP0140338 (Taberdivarine H)

3D SDF for NP0140338 (Taberdivarine H)

3D-SDF for NP0140338 (Taberdivarine H)

PDB for NP0140338 (Taberdivarine H)

3D PDB for NP0140338 (Taberdivarine H)

SMILES for NP0140338 (Taberdivarine H)

INCHI for NP0140338 (Taberdivarine H)

Structure for NP0140338 (Taberdivarine H)

3D Structure for NP0140338 (Taberdivarine H)