NP-MRD: Showing NP-Card for (1r,9r,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one (NP0222016)

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Record Information

Version

2.0

Created at

2022-09-05 23:44:26 UTC

Updated at

2022-09-05 23:44:26 UTC

NP-MRD ID

NP0222016

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,9r,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one

Description

Ajmalidine 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. (1r,9r,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one is found in Rauvolfia serpentina. Based on a literature review very few articles have been published on Ajmalidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062201442D          

 24 29  0  0  1  0            999 V2000
   -1.2724    0.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772    0.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106    0.2870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9791    0.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9515    1.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5871    0.4291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4498    0.5739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0204    1.2285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    2.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6572    0.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    0.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    0.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1969   -0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451   -0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6786   -0.2627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1182   -1.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140   -1.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7535   -0.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022   -0.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9651   -1.7161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676   -0.3823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173   -0.5325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2709   -1.1975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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  6  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 18 22  1  0  0  0  0
  6 22  1  1  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  6  0  0  0
M  END

     RDKit          3D

 48 53  0  0  0  0  0  0  0  0999 V2000
   -4.3722   -1.2428   -1.6322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8974    0.1034   -1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0513   -0.1631    0.1104 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8589   -1.0835   -0.1944 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1823   -1.2090    1.1793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440    0.0673    1.3788 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0045   -0.2695    0.9121 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1282    0.3826    1.4718 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2153    1.1285    2.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1995    0.1473    0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5863    0.1297    0.7123 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4289   -0.1373   -0.3452 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9049   -0.3935   -1.5783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5154   -0.3774   -1.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6672   -0.1145   -0.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2354   -0.0255   -0.5696 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6731    1.3321   -0.9670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7961    1.0499   -0.7689 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0076   -0.3690   -1.1882 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3847   -0.9461   -1.3017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6388   -1.9763   -1.9045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0243    1.1122    0.6814 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858    1.0297    0.8039 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8637    1.1295    2.1390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0781   -1.0901   -2.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183   -1.8150   -2.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8418   -1.7815   -0.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4285    0.6233   -1.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7733    0.6783   -0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6981   -0.7007    0.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1933   -2.0822   -0.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709   -2.1117    1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410   -1.2469    1.9897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3428    0.3276    2.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2005   -1.3814    1.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2967    0.3770    3.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3088    1.7392    2.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1438    1.7341    2.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0223    0.3351    1.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5122   -0.1491   -0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5809   -0.6012   -2.3965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1773   -0.5918   -2.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0211    2.1126   -0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9476    1.4933   -2.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4466    1.7873   -1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4684   -0.4795   -2.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8756    1.9488    0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7328    1.5697    2.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 23  1  0
 23 24  1  0
 23 22  1  0
 22 18  1  0
 18 17  1  0
 17 16  1  0
 16  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 19  1  0
 19 20  1  0
 20 21  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4  3  1  0
 15 10  1  0
  6 22  1  0
 19 18  1  0
 16 20  1  6
 15 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  2 29  1  0
  3 30  1  1
 23 47  1  6
 24 48  1  0
 18 45  1  6
 17 43  1  0
 17 44  1  0
  7 35  1  6
  6 34  1  1
  5 32  1  0
  5 33  1  0
  4 31  1  6
 19 46  1  6
  9 36  1  0
  9 37  1  0
  9 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 14 42  1  0
M  END


  Mrv1652309062201442D          

 24 29  0  0  1  0            999 V2000
   -1.2724    0.6461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4772    0.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106    0.2870    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9791    0.1877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9515    1.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5871    0.4291    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4498    0.5739    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0204    1.2285    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637    2.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6572    0.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4211    0.9859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0729    0.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9608   -0.3372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1969   -0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5451   -0.1430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6786   -0.2627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1182   -1.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140   -1.1684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7535   -0.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022   -0.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9651   -1.7161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676   -0.3823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173   -0.5325    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2709   -1.1975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  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  6  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  6  0  0  0
 18 17  1  6  0  0  0
 18 19  1  0  0  0  0
  4 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  2  0  0  0  0
 18 22  1  0  0  0  0
  6 22  1  1  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 23 24  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0222016

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1[C@@H](O)N2[C@H]3C[C@@]45[C@H]([C@@H]2CC1C3C4=O)N(C)C1=CC=CC=C51

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-17,19,24H,3,8-9H2,1-2H3/t10-,11?,14-,15-,16?,17-,19+,20+/m0/s1

> <INCHI_KEY>
JLUFXYAXVHAFTF-QKYULUPMSA-N

> <FORMULA>
C20H24N2O2

> <MOLECULAR_WEIGHT>
324.424

> <EXACT_MASS>
324.183778021

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.04484457100402

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,9R,10S,13S,14R,16S)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-18-one

> <JCHEM_LOGP>
2.7066996776666654

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.838080916315487

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.324717441604463

> <JCHEM_PKA_STRONGEST_BASIC>
6.493255207118143

> <JCHEM_POLAR_SURFACE_AREA>
43.78

> <JCHEM_REFRACTIVITY>
91.79119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,9R,10S,13S,14R,16S)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-18-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.375   1.206   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.891   1.616   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.207   0.536   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.828   0.350   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.776   1.908   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.963   0.801   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.573   1.071   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       5.638   2.293   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       5.532   3.829   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.827   1.259   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.253   1.840   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.469   0.896   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.260  -0.629   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.834  -1.211   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.618  -0.267   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.000  -0.490   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.954  -2.009   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.453  -2.181   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.273  -0.843   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.857  -1.820   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.535  -3.203   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       1.993  -0.714   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       0.406  -0.994   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.506  -2.235   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15    7   17   20                                             
CONECT   17   16   18                                                       
CONECT   18   17   19   22                                                  
CONECT   19   18    4   20                                                  
CONECT   20   19   16   21                                                  
CONECT   21   20                                                            
CONECT   22   18    6   23                                                  
CONECT   23   22    3   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄N₂O₂

Average Mass

324.4240 Da

Monoisotopic Mass

324.18378 Da

IUPAC Name

(1R,9R,10S,13S,14R,16S)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-18-one

Traditional Name

(1R,9R,10S,13S,14R,16S)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6-trien-18-one

CAS Registry Number

Not Available

SMILES

CC[C@@H]1[C@@H](O)N2[C@H]3C[C@@]45[C@H]([C@@H]2CC1C3C4=O)N(C)C1=CC=CC=C51

InChI Identifier

InChI=1S/C20H24N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-17,19,24H,3,8-9H2,1-2H3/t10-,11?,14-,15-,16?,17-,19+,20+/m0/s1

InChI Key

JLUFXYAXVHAFTF-QKYULUPMSA-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 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
Pyridoindole
Beta-carboline
Quinolizidine
Indole or derivatives
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Quinuclidine
Aralkylamine
Azepane
Benzenoid
Piperidine
Tertiary amine
Ketone
Hemiaminal
Azacycle
Organoheterocyclic compound
Alkanolamine
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	2.71	ChemAxon
pKa (Strongest Acidic)	13.32	ChemAxon
pKa (Strongest Basic)	6.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.78 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	91.79 m³·mol⁻¹	ChemAxon
Polarizability	36.04 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

C00024298

Chemspider ID

58802290

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131676019

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,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one (NP0222016)

MOL for NP0222016 ((1r,9r,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one)

3D MOL for NP0222016 ((1r,9r,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one)

3D SDF for NP0222016 ((1r,9r,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one)

3D-SDF for NP0222016 ((1r,9r,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one)

PDB for NP0222016 ((1r,9r,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one)

3D PDB for NP0222016 ((1r,9r,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one)

SMILES for NP0222016 ((1r,9r,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one)

INCHI for NP0222016 ((1r,9r,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one)

Structure for NP0222016 ((1r,9r,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one)

3D Structure for NP0222016 ((1r,9r,10s,13s,14r,16s)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6-trien-18-one)