NP-MRD: Showing NP-Card for 16-epivellosimine (NP0222665)

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Record Information

Version

2.0

Created at

2022-09-06 00:33:28 UTC

Updated at

2022-09-06 00:33:28 UTC

NP-MRD ID

NP0222665

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-epivellosimine

Description

16-epivellosimine is found in Rauvolfia salicifolia. 16-epivellosimine was first documented in 1983 (PMID: 17404987).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652303082006162D          

 25 29  0  0  0  0            999 V2000
   -0.4954   -1.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623   -1.1464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1218   -0.6615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8164   -0.0299    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1483    0.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8007   -0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7606   -1.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7183   -1.8953    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7218   -2.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4734   -1.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3560   -1.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0577   -0.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1391   -1.8394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2949   -1.4049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7889   -0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0606   -1.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7218   -0.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4502    0.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4165   -0.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7148    0.6607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5669    0.6607    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2938    1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983    2.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4930    1.4047    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
 12  3  1  0  0  0  0
  2  1  1  0  0  0  0
  6  1  2  0  0  0  0
  5  6  1  0  0  0  0
  7  2  1  0  0  0  0
  2 13  1  6  0  0  0
  5  4  1  0  0  0  0
 11  8  1  0  0  0  0
  7  8  1  0  0  0  0
 12 11  1  0  0  0  0
 10 11  2  0  0  0  0
  9 10  1  0  0  0  0
 14  1  1  0  0  0  0
 15 14  1  0  0  0  0
 16  6  1  0  0  0  0
 17 15  1  0  0  0  0
 16 15  2  0  0  0  0
 18 17  2  0  0  0  0
 19 16  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  2  0  0  0  0
  8 21  1  1  0  0  0
  4 21  1  1  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  END

     RDKit          3D

 42 46  0  0  0  0  0  0  0  0999 V2000
    4.8743    1.0327   -0.5746 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0560    1.0494    0.6414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8647    0.5233    0.6437 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0263    0.5370    1.8765 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6870    0.2197    1.4567 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3246    1.1019    0.3364 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0547    0.7193   -0.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2272   -0.1259   -0.5360 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6532   -1.4434    0.0058 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1899   -2.3135   -1.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3655   -3.5237   -1.0757 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6050   -1.1701    1.0331 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7696   -1.5690    0.6130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6190   -0.3880    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164    0.8825    0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0940    1.7344   -0.2062 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2708    1.0707   -0.2981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5540    1.4753   -0.5977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5368    0.5163   -0.6029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2813   -0.8028   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9887   -1.1686   -0.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9736   -0.2504   -0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3031    1.1283   -1.5170 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5547    0.1317   -0.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5608    1.9043   -0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4553    1.5036    1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0544    1.5136    2.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3719   -0.2926    2.5284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5724    2.1432    0.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769    0.2140   -1.6500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3954    1.6528   -1.4681 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173   -0.3547   -1.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5095   -1.9453    0.5011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6808   -1.9219   -1.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8298   -1.7553    1.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3174   -2.1541    1.3846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7632   -2.2323   -0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0393    2.7711   -0.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8025    2.5079   -0.8244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5608    0.8359   -0.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0838   -1.5542   -0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7398   -2.2033    0.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  2  0
 10  9  1  0
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 22  2  0
 22 21  1  0
 21 20  2  0
 20 19  1  0
 19 18  2  0
 15  6  1  0
  6  7  1  0
  7  8  1  0
  8  3  1  0
  3  4  1  0
  4  5  1  0
  3  2  2  0
  2  1  1  0
  8  9  1  0
  5 12  1  0
 22 14  1  0
  5  6  1  0
 18 17  1  0
 10 34  1  0
  9 33  1  1
 12 35  1  1
 13 36  1  0
 13 37  1  0
 16 38  1  0
 21 42  1  0
 20 41  1  0
 19 40  1  0
 18 39  1  0
  6 29  1  1
  7 30  1  0
  7 31  1  0
  8 32  1  6
  4 27  1  0
  4 28  1  0
  2 26  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
M  END


  Mrv1652303082006162D          

 25 29  0  0  0  0            999 V2000
   -0.4954   -1.0147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4623   -1.1464    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1218   -0.6615    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8164   -0.0299    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1483    0.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8007   -0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7606   -1.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7183   -1.8953    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7218   -2.0911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4734   -1.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3560   -1.4150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0577   -0.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1391   -1.8394    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2949   -1.4049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0942   -1.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7889   -0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0606   -1.1526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7218   -0.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4502    0.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4165   -0.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7148    0.6607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5669    0.6607    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2938    1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983    2.0911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4930    1.4047    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
 12  3  1  0  0  0  0
  2  1  1  0  0  0  0
  6  1  2  0  0  0  0
  5  6  1  0  0  0  0
  7  2  1  0  0  0  0
  2 13  1  6  0  0  0
  5  4  1  0  0  0  0
 11  8  1  0  0  0  0
  7  8  1  0  0  0  0
 12 11  1  0  0  0  0
 10 11  2  0  0  0  0
  9 10  1  0  0  0  0
 14  1  1  0  0  0  0
 15 14  1  0  0  0  0
 16  6  1  0  0  0  0
 17 15  1  0  0  0  0
 16 15  2  0  0  0  0
 18 17  2  0  0  0  0
 19 16  1  0  0  0  0
 20 18  1  0  0  0  0
 20 19  2  0  0  0  0
  8 21  1  1  0  0  0
  4 21  1  1  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222665

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(=O)[C@]1([H])[C@@H]2CC3=C(NC4=C3C=CC=C4)[C@]3([H])C[C@H]1\C(CN23)=C/C

> <INCHI_IDENTIFIER>
InChI=1S/C19H20N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,10,13,15,17-18,20H,7-9H2,1H3/b11-2-/t13-,15-,17-,18-/m0/s1

> <INCHI_KEY>
MHASSCPGKAMILD-MIOJWWSHSA-N

> <FORMULA>
C19H20N2O

> <MOLECULAR_WEIGHT>
292.3749

> <EXACT_MASS>
292.157563272

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.13974889256542

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,12S,13S,14R,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4(9),5,7-tetraene-13-carbaldehyde

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.458632152

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.185850226852736

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.290052809775592

> <JCHEM_PKA_STRONGEST_BASIC>
5.754158195027056

> <JCHEM_POLAR_SURFACE_AREA>
36.1

> <JCHEM_REFRACTIVITY>
88.1798

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,12S,13S,14R,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4(9),5,7-tetraene-13-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-MAR-20         0                                  
HETATM    1  C   UNK     0      -0.925  -1.894   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.863  -2.140   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.094  -1.235   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.524  -0.056   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.277   0.218   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.495  -0.715   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.420  -3.291   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.207  -3.538   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.947  -3.903   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.484  -2.944   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.398  -2.641   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.841  -1.490   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       0.260  -3.434   0.000  0.00  0.00           H+0
HETATM   14  N   UNK     0      -2.417  -2.622   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -3.909  -1.894   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.339  -0.715   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.713  -2.152   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.947  -1.231   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.574   0.206   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.377  -0.052   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.201   1.233   0.000  0.00  0.00           C+0
HETATM   22  H   UNK     0       4.792   1.233   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       2.415   2.613   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.170   3.903   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0       0.920   2.622   0.000  0.00  0.00           H+0
CONECT    1    2    6   14                                                  
CONECT    2    3    1    7   13                                             
CONECT    3    2    4   12                                                  
CONECT    4    3    5   21                                                  
CONECT    5    6    4                                                       
CONECT    6    1    5   16                                                  
CONECT    7    2    8                                                       
CONECT    8   11    7   21                                                  
CONECT    9   10                                                            
CONECT   10   11    9                                                       
CONECT   11    8   12   10                                                  
CONECT   12    3   11                                                       
CONECT   13    2                                                            
CONECT   14    1   15                                                       
CONECT   15   14   17   16                                                  
CONECT   16    6   15   19                                                  
CONECT   17   15   18                                                       
CONECT   18   17   20                                                       
CONECT   19   16   20                                                       
CONECT   20   18   19                                                       
CONECT   21    8    4   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Value	Source
16-Epi-vellosimine	MeSH

Chemical Formula

C₁₉H₂₀N₂O

Average Mass

292.3749 Da

Monoisotopic Mass

292.15756 Da

IUPAC Name

(1S,12S,13S,14R,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4(9),5,7-tetraene-13-carbaldehyde

Traditional Name

(1S,12S,13S,14R,15E)-15-ethylidene-3,17-diazapentacyclo[12.3.1.0^{2,10}.0^{4,9}.0^{12,17}]octadeca-2(10),4(9),5,7-tetraene-13-carbaldehyde

CAS Registry Number

Not Available

SMILES

[H]C(=O)[C@]1([H])[C@@H]2CC3=C(NC4=C3C=CC=C4)[C@]3([H])C[C@H]1\C(CN23)=C/C

InChI Identifier

InChI=1S/C19H20N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,10,13,15,17-18,20H,7-9H2,1H3/b11-2-/t13-,15-,17-,18-/m0/s1

InChI Key

MHASSCPGKAMILD-MIOJWWSHSA-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

Species Name	Source	Reference
Rauvolfia salicifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Sarpagine-skeleton
Vobasan skeleton
Beta-carboline
Pyridoindole
3-alkylindole
Indole
Indole or derivatives
Quinuclidine
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:16425 )
indole alkaloid (CHEBI:16425 )
aldehyde (CHEBI:16425 )

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	2.51	ALOGPS
logP	2.46	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	15.29	ChemAxon
pKa (Strongest Basic)	5.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	36.1 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.18 m³·mol⁻¹	ChemAxon
Polarizability	33.14 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

FDB030270

KNApSAcK ID

C00045433 C00048226

Chemspider ID

Not Available

KEGG Compound ID

C11633

BioCyc ID

16-EPIVELLOSIMINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11335328

PDB ID

Not Available

ChEBI ID

16425

Good Scents ID

Not Available

References

General References

Yin W, Kabir MS, Wang Z, Rallapalli SK, Ma J, Cook JM: Enantiospecific total synthesis of the important biogenetic intermediates along the ajmaline pathway, (+)-polyneuridine and (+)-polyneuridine aldehyde, as well as 16-epivellosimine and macusine A. J Org Chem. 2010 May 21;75(10):3339-49. doi: 10.1021/jo100279w. [PubMed:20392128 ]
Pfitzner A, Stockigt J: Characterization of polyneuridine aldehyde esterase, a key enzyme in the biosynthesis of sarpagine/ajmaline type alkaloids. Planta Med. 1983 Aug;48(8):221-7. doi: 10.1055/s-2007-969924. [PubMed:17404987 ]
LOTUS database [Link]

Showing NP-Card for 16-epivellosimine (NP0222665)

MOL for NP0222665 (16-epivellosimine)

3D MOL for NP0222665 (16-epivellosimine)

3D SDF for NP0222665 (16-epivellosimine)

3D-SDF for NP0222665 (16-epivellosimine)

PDB for NP0222665 (16-epivellosimine)

3D PDB for NP0222665 (16-epivellosimine)

SMILES for NP0222665 (16-epivellosimine)

INCHI for NP0222665 (16-epivellosimine)

Structure for NP0222665 (16-epivellosimine)

3D Structure for NP0222665 (16-epivellosimine)