NP-MRD: Showing NP-Card for (1r,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate (NP0208322)

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Record Information

Version

2.0

Created at

2022-09-05 05:16:37 UTC

Updated at

2022-09-05 05:16:37 UTC

NP-MRD ID

NP0208322

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate

Description

ZINC255269492 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,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate is found in Alstonia yunnanensis. Based on a literature review very few articles have been published on ZINC255269492.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052207162D          

 26 31  0  0  1  0            999 V2000
   -0.2779   -1.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4852   -0.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1027    0.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2093    0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597    0.7543    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    0.6020    0.0679    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.5792   -0.0571    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9435   -0.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9711    0.1843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7456    0.8234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3060    1.5404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1103    1.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6707    0.6347    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4418   -0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125   -0.8565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6493   -0.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4132   -0.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0650   -0.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529    0.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1890    1.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372    0.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5942    1.3472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9571    2.0881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4969    2.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6738    2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8598    3.5137    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  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 13 21  1  0  0  0  0
 13 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  CHG  2   5   1   6  -1
M  END

     RDKit          3D

 48 53  0  0  0  0  0  0  0  0999 V2000
   -4.7634   -0.2541   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1249   -1.4838    0.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8319   -1.6243    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0594   -2.8271    0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6584   -2.3766    0.5080 N   0  0  1  0  0  4  0  0  0  0  0  0
    0.1343   -3.3159    1.0386 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1860   -2.0962   -0.8447 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1327   -1.2488   -1.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0433   -0.5486   -0.6206 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1542    0.0173    0.4950 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6761   -1.1478    1.3139 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7849   -0.7646    1.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1656   -0.2442    0.2307 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1000   -1.3457   -0.7394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2473   -1.4110   -1.3118 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1526   -0.4291   -0.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4663   -0.1411   -1.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1389    0.8823   -0.5241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4963    1.6337    0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864    1.3258    0.7517 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4979    0.3096    0.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0546    0.7281   -0.0573 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1914    1.9459    0.6013 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2602    3.1174   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4045    4.4613    0.4449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1961    3.0528   -1.4112 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8610   -0.3599   -0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4757    0.6137    0.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5934   -0.0505   -1.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7089   -2.2829    0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0757   -3.6280   -0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3644   -3.1737    1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0127   -3.0883   -1.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8164   -1.9394   -2.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6888   -0.5793   -2.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6119    0.2647   -1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7940    0.7184    1.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399   -1.3246    2.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7539    0.0572    2.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3675   -1.6402    1.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9897   -0.7069   -1.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1786    1.1049   -0.7872 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0541    2.4265    0.9152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6945    1.9166    1.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0189    0.8842   -1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    4.4668    1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0085    5.1413   -0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5885    4.9640    0.5815 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  1
  5 11  1  0
 11 12  1  0
 12 13  1  0
 13 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 22 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9  3  1  0
 21 16  1  0
  7  5  1  0
 10 11  1  0
 14 13  1  0
 13 21  1  1
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  4 31  1  0
  4 32  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 22 45  1  6
 25 46  1  0
 25 47  1  0
 25 48  1  0
 10 37  1  1
  9 36  1  6
  8 34  1  0
  8 35  1  0
  7 33  1  6
 17 41  1  0
 18 42  1  0
 19 43  1  0
 20 44  1  0
M  CHG  2   5   1   6  -1
M  END


  Mrv1652309052207162D          

 26 31  0  0  1  0            999 V2000
   -0.2779   -1.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4852   -0.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1027    0.0850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2093    0.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0597    0.7543    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    0.6020    0.0679    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.5792   -0.0571    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9435   -0.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9711    0.1843    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7456    0.8234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3060    1.5404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1103    1.4482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6707    0.6347    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4418   -0.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125   -0.8565    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6493   -0.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4132   -0.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0650   -0.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9529    0.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1890    1.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372    0.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5942    1.3472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9571    2.0881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4969    2.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6738    2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8598    3.5137    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  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 13 21  1  0  0  0  0
 13 22  1  0  0  0  0
 10 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  CHG  2   5   1   6  -1
M  END
> <DATABASE_ID>
NP0208322

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\C[N@+]2([O-])[C@H]3C[C@]45[C@H](OC(C)=O)[C@H]3[C@H]1C[C@H]2C4=NC1=CC=CC=C51

> <INCHI_IDENTIFIER>
InChI=1S/C21H22N2O3/c1-3-12-10-23(25)16-8-13(12)18-17(23)9-21(20(18)26-11(2)24)14-6-4-5-7-15(14)22-19(16)21/h3-7,13,16-18,20H,8-10H2,1-2H3/b12-3-/t13-,16-,17-,18-,20+,21+,23+/m0/s1

> <INCHI_KEY>
SYZGOUOZLCZRJD-RLBSKOTMSA-N

> <FORMULA>
C21H22N2O3

> <MOLECULAR_WEIGHT>
350.418

> <EXACT_MASS>
350.163042576

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.66708148104196

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,10S,12R,13E,15S,16S,17S,18R)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-15-ium-15-olate

> <JCHEM_LOGP>
1.6477641539999988

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.369320268478972

> <JCHEM_POLAR_SURFACE_AREA>
61.720000000000006

> <JCHEM_REFRACTIVITY>
99.2788

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,10S,12R,13E,15S,16S,17S,18R)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-15-ium-15-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.519  -2.412   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.906  -0.922   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.192   0.159   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.391   1.688   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.978   1.408   0.000  0.00  0.00           N+1
HETATM    6  O   UNK     0       1.124   0.127   0.000  0.00  0.00           O-1
HETATM    7  C   UNK     0       2.948  -0.107   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.761  -1.214   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.813   0.344   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.258   1.537   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.438   2.875   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.939   2.703   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.985   1.185   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.558  -0.377   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       5.623  -1.599   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       6.812  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.238  -1.146   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.455  -0.202   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.245   1.324   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.819   1.905   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.603   0.961   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.843   2.515   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.520   3.898   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.661   5.176   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.124   5.071   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.338   6.559   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11   22                                                  
CONECT   11   10    5   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   21   22                                             
CONECT   14   13    7   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   13                                                  
CONECT   22   13   10   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   62    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,15S,16S,17S,18R)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-15-ium-15-olate

Traditional Name

(1R,10S,12R,13E,15S,16S,17S,18R)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0^{1,9}.0^{2,7}.0^{10,15}.0^{12,17}]nonadeca-2,4,6,8-tetraen-15-ium-15-olate

CAS Registry Number

Not Available

SMILES

C\C=C1\C[N@+]2([O-])[C@H]3C[C@]45[C@H](OC(C)=O)[C@H]3[C@H]1C[C@H]2C4=NC1=CC=CC=C51

InChI Identifier

InChI=1S/C21H22N2O3/c1-3-12-10-23(25)16-8-13(12)18-17(23)9-21(20(18)26-11(2)24)14-6-4-5-7-15(14)22-19(16)21/h3-7,13,16-18,20H,8-10H2,1-2H3/b12-3-/t13-,16-,17-,18-,20+,21+,23+/m0/s1

InChI Key

SYZGOUOZLCZRJD-RLBSKOTMSA-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
Alstonia yunnanensis	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
Trialkyl amine oxide
Carboxylic acid ester
Ketimine
N-oxide
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Trisubstituted n-oxide
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Imine
Organic zwitterion
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	1.65	ChemAxon
pKa (Strongest Basic)	3.37	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.72 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.28 m³·mol⁻¹	ChemAxon
Polarizability	37.67 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124928677

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate (NP0208322)

MOL for NP0208322 ((1r,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate)

3D MOL for NP0208322 ((1r,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate)

3D SDF for NP0208322 ((1r,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate)

3D-SDF for NP0208322 ((1r,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate)

PDB for NP0208322 ((1r,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate)

3D PDB for NP0208322 ((1r,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate)

SMILES for NP0208322 ((1r,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate)

INCHI for NP0208322 ((1r,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate)

Structure for NP0208322 ((1r,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate)

3D Structure for NP0208322 ((1r,10s,12r,13e,15s,16s,17s,18r)-18-(acetyloxy)-13-ethylidene-8,15-diazahexacyclo[14.2.1.0¹,⁹.0²,⁷.0¹⁰,¹⁵.0¹²,¹⁷]nonadeca-2,4,6,8-tetraen-15-ium-15-olate)