NP-MRD: Showing NP-Card for vomilenine (NP0285661)

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Record Information

Version

2.0

Created at

2022-09-09 13:55:39 UTC

Updated at

2022-09-09 13:55:39 UTC

NP-MRD ID

NP0285661

Secondary Accession Numbers

None

Natural Product Identification

Common Name

vomilenine

Description

vomilenine is found in Rauvolfia biauriculata, Rauvolfia sellowii and Rauvolfia serpentina. vomilenine was first documented in 1999 (PMID: 10234858).

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv1533007211514582D          
 
 28 33  0  0  1  0            999 V2000
   15.5512  -14.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5512  -15.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2657  -15.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9802  -15.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9802  -14.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2657  -14.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6947  -15.8400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4091  -15.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4091  -14.6025    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1236  -15.8400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.8381  -15.4275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8381  -14.6025    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1236  -14.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1236  -16.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8381  -17.0775    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.5525  -16.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5525  -15.8400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.2670  -17.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2670  -17.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4091  -16.2525    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5525  -14.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0617  -13.6067    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.3494  -13.9765    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0617  -12.7817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3472  -12.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6327  -12.7817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3472  -11.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2670  -15.4275    0.0000 O   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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9  5  1  6  0  0  0
  8 10  1  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
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 10 20  1  6  0  0  0
 12 21  1  1  0  0  0
 15 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  9 22  1  0  0  0  0
 22 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 17 28  1  6  0  0  0
M  END

     RDKit          3D

 48 53  0  0  0  0  0  0  0  0999 V2000
    4.8412    0.7087    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3414   -0.4887   -0.5151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0815   -0.8135   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261   -0.0053    0.3423 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5072   -1.0296    1.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7465   -2.0017    0.4419 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6905   -1.6398    0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7008   -2.1121    1.2174 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8841   -1.3591    1.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1876   -1.5094    1.4853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1884   -0.6356    1.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8726    0.4010    0.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5803    0.5441   -0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5686   -0.3211    0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1569   -0.4584   -0.1513 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8624   -0.6845   -1.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664   -0.6994   -1.5622 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9717    0.4085   -0.5887 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2889    0.7205    0.1644 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8539    1.9038   -0.4116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1319    3.0354    0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7229    4.2573   -0.2904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8694    3.0012    1.5809 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1074   -1.9609   -0.9458 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5494   -1.9955   -1.1560 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1259   -3.1822   -0.8009 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2239    1.6149   -0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9425    0.5384    1.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8530    0.9527   -0.1708 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0709   -1.0815   -1.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5539    0.8474    0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9203   -0.5637    2.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3859   -1.5167    1.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8896   -3.0250    0.8199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4352   -2.3274    2.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2133   -0.7414    1.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6728    1.0780    0.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3311    1.3611   -0.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2743   -1.6501   -1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1889    0.1702   -2.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1241   -0.5663   -2.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3347    1.3239   -1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1549    0.9298    1.2246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0984    4.5627   -1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6565    5.0779    0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7774    4.0854   -0.5930 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7019   -1.8330   -2.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2965   -3.3209    0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 15 14  1  6
 14  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  3 25  1  0
 25 26  1  0
 25 24  1  0
 19 18  1  0
 13 14  1  0
 24  6  1  0
  4 18  1  0
 24 17  1  0
  7 15  1  0
 18 42  1  6
 17 41  1  6
 16 39  1  0
 16 40  1  0
 19 43  1  1
 22 44  1  0
 22 45  1  0
 22 46  1  0
 10 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
  6 34  1  1
  5 32  1  0
  5 33  1  0
  4 31  1  1
  2 30  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
 25 47  1  6
 26 48  1  0
M  END

 
  Mrv1533007211514582D          
 
 28 33  0  0  1  0            999 V2000
   15.5512  -14.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5512  -15.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2657  -15.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9802  -15.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9802  -14.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2657  -14.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6947  -15.8400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4091  -15.4275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4091  -14.6025    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1236  -15.8400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.8381  -15.4275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8381  -14.6025    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.1236  -14.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1236  -16.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8381  -17.0775    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   20.5525  -16.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5525  -15.8400    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.2670  -17.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2670  -17.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4091  -16.2525    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.5525  -14.1900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0617  -13.6067    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   21.3494  -13.9765    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.0617  -12.7817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3472  -12.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6327  -12.7817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3472  -11.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2670  -15.4275    0.0000 O   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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9  5  1  6  0  0  0
  8 10  1  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
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 10 20  1  6  0  0  0
 12 21  1  1  0  0  0
 15 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
  9 22  1  0  0  0  0
 22 24  1  6  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 17 28  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0285661

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C12[C@@H]3C[C@@]4([C@@H]1OC(C)=O)C1=C(C=CC=C1)N=C4[C@]1([H])C[C@H]2\C(=C/C)[C@@H](O)N31

> <INCHI_IDENTIFIER>
InChI=1S/C21H22N2O3/c1-3-11-12-8-15-18-21(13-6-4-5-7-14(13)22-18)9-16(23(15)20(11)25)17(12)19(21)26-10(2)24/h3-7,12,15-17,19-20,25H,8-9H2,1-2H3/b11-3+/t12-,15-,16-,17?,19+,20+,21+/m0/s1

> <INCHI_KEY>
BERYBAUEDCRDKM-FDHUPVAHSA-N

> <FORMULA>
C21H22N2O3

> <MOLECULAR_WEIGHT>
350.418

> <EXACT_MASS>
350.163042576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.830295859994074

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,10S,12R,13E,14R,16S,18R)-13-ethylidene-14-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2(7),3,5,8-tetraen-18-yl acetate

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
2.4079153956666657

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.981267144857306

> <JCHEM_PKA_STRONGEST_BASIC>
5.140194472436635

> <JCHEM_POLAR_SURFACE_AREA>
62.129999999999995

> <JCHEM_REFRACTIVITY>
98.2638

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10S,12R,13E,14R,16S,18R)-13-ethylidene-14-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2(7),3,5,8-tetraen-18-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-JUL-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUL-15         0                                  
HETATM    1  C   UNK     0      29.029 -27.258   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.029 -28.798   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.363 -29.568   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.696 -28.798   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.696 -27.258   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.363 -26.488   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      33.030 -29.568   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      34.364 -28.798   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.364 -27.258   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      35.697 -29.568   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      37.031 -28.798   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      37.031 -27.258   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.697 -26.488   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.697 -31.108   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.031 -31.878   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      38.365 -31.108   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      38.365 -29.568   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      39.698 -31.878   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      39.698 -33.418   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0      34.364 -30.338   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0      38.365 -26.488   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      35.582 -25.399   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      39.852 -26.089   0.000  0.00  0.00           H+0
HETATM   24  O   UNK     0      35.582 -23.859   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      34.248 -23.089   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      32.914 -23.859   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      34.248 -21.549   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      39.698 -28.798   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    5   13   22                                             
CONECT   10    8   11   14   20                                             
CONECT   11   10   12   17                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12    9                                                       
CONECT   14   10   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   11   28                                                  
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   10                                                            
CONECT   21   12   15   22   23                                             
CONECT   22   21    9   24                                                  
CONECT   23   21                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   17                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₂N₂O₃

Average Mass

350.4180 Da

Monoisotopic Mass

350.16304 Da

IUPAC Name

(1R,10S,12R,13E,14R,16S,18R)-13-ethylidene-14-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2(7),3,5,8-tetraen-18-yl acetate

Traditional Name

(1R,10S,12R,13E,14R,16S,18R)-13-ethylidene-14-hydroxy-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2(7),3,5,8-tetraen-18-yl acetate

CAS Registry Number

Not Available

SMILES

[H]C12[C@@H]3C[C@@]4([C@@H]1OC(C)=O)C1=C(C=CC=C1)N=C4[C@]1([H])C[C@H]2\C(=C/C)[C@@H](O)N31

InChI Identifier

InChI=1S/C21H22N2O3/c1-3-11-12-8-15-18-21(13-6-4-5-7-14(13)22-18)9-16(23(15)20(11)25)17(12)19(21)26-10(2)24/h3-7,12,15-17,19-20,25H,8-9H2,1-2H3/b11-3+/t12-,15-,16-,17?,19+,20+,21+/m0/s1

InChI Key

BERYBAUEDCRDKM-FDHUPVAHSA-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 biauriculata	LOTUS Database	35616633
Rauvolfia sellowii	LOTUS Database	35616633
Rauvolfia serpentina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ajmaline-sarpagine alkaloids. These are organic compounds containing either of the ajmalan, sarpagan skeleton, or derivative thereof. The Sarpagine (Akuammidine) group, based on the sarpagan nucleus, arises from bond formation between C-16 and C-5 of the corynantheine precursor. Ajmaline alkaloids are based on a 17,19-secoyohimban skeleton (oxayohimban) which is invariably present as an ether.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ajmaline-sarpagine alkaloids

Sub Class

Not Available

Direct Parent

Ajmaline-sarpagine alkaloids

Alternative Parents

Substituents

Sarpagine-skeleton
Quinolizidine
3-alkylindole
Indole or derivatives
Quinuclidine
Azepane
Piperidine
Benzenoid
Carboxylic acid ester
Ketimine
Organoheterocyclic compound
Azacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Carboxylic acid derivative
Alkanolamine
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organopnictogen compound
Imine
Organic nitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indole alkaloid (CHEBI:16408 )
hemiaminal (CHEBI:16408 )
Indole alkaloids (C01761 )

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	2.14	ALOGPS
logP	2.41	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	12.98	ChemAxon
pKa (Strongest Basic)	5.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	98.26 m³·mol⁻¹	ChemAxon
Polarizability	37.83 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00024338

Chemspider ID

Not Available

KEGG Compound ID

C01761

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Vomilenine

METLIN ID

Not Available

PubChem Compound

11953806

PDB ID

Not Available

ChEBI ID

16408

Good Scents ID

Not Available

References

General References

Warzecha H, Obitz P, Stockigt J: Purification, partial amino acid sequence and structure of the product of raucaffricine-O-beta-D-glucosidase from plant cell cultures of Rauwolfia serpentina. Phytochemistry. 1999 Apr;50(7):1099-109. doi: 10.1016/s0031-9422(98)00689-x. [PubMed:10234858 ]
von Schumann G, Gao S, Stockigt J: Vomilenine reductase--a novel enzyme catalyzing a crucial step in the biosynthesis of the therapeutically applied antiarrhythmic alkaloid ajmaline. Bioorg Med Chem. 2002 Jun;10(6):1913-8. doi: 10.1016/s0968-0896(01)00435-7. [PubMed:11937349 ]
Madhusudanan KP, Banerjee S, Khanuja SP, Chattopadhyay SK: Analysis of hairy root culture of Rauvolfia serpentina using direct analysis in real time mass spectrometric technique. Biomed Chromatogr. 2008 Jun;22(6):596-600. doi: 10.1002/bmc.974. [PubMed:18205139 ]
LOTUS database [Link]

Showing NP-Card for vomilenine (NP0285661)

MOL for NP0285661 (vomilenine)

3D MOL for NP0285661 (vomilenine)

3D SDF for NP0285661 (vomilenine)

3D-SDF for NP0285661 (vomilenine)

PDB for NP0285661 (vomilenine)

3D PDB for NP0285661 (vomilenine)

SMILES for NP0285661 (vomilenine)

INCHI for NP0285661 (vomilenine)

Structure for NP0285661 (vomilenine)

3D Structure for NP0285661 (vomilenine)