NP-MRD: Showing NP-Card for (11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate (NP0304632)

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Record Information

Version

2.0

Created at

2022-09-10 19:52:20 UTC

Updated at

2022-09-10 19:52:20 UTC

NP-MRD ID

NP0304632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate

Description

Echitamidine N-oxide belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton. (11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate is found in Alstonia rostrata. (11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate was first documented in 2004 (PMID: 15387668). Based on a literature review very few articles have been published on Echitamidine N-oxide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102221522D          

 26 30  0  0  1  0            999 V2000
    1.4781    3.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4797    3.0533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1949    2.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    3.0560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1965    1.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0003    1.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7602    1.7571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3466    1.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1713    1.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6027    0.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2094   -0.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9533    0.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0766    0.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2714   -0.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5881   -0.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8791   -0.3673    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.5359   -1.1175    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.0348   -0.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8011    0.7067    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0039    0.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5629    0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2497    1.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3921    1.3975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7871    0.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2946    0.3105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 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
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  1  6  0  0  0
 20 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  6  0  0  0
 26 25  1  1  0  0  0
 14 26  1  0  0  0  0
 17 26  1  0  0  0  0
M  CHG  2  17   1  18  -1
M  END

     RDKit          3D

 50 54  0  0  0  0  0  0  0  0999 V2000
   -2.1000    4.3976    0.8237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6746    3.1731    0.3191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4882    2.5523    0.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356    3.1692    1.2870 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1832    1.2764   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0524    0.7470    0.1810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2659    1.4223    0.4019 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3557    0.4955    0.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7324    0.6957    0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5623   -0.3142   -0.3780 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0204   -1.5190   -0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6370   -1.7156   -0.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8143   -0.7128   -0.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4001   -0.6579    0.1452 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1954   -1.4953    1.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1846   -2.5926    0.9460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5892   -1.6472    0.2474 N   0  0  2  0  0  4  0  0  0  0  0  0
   -0.8403   -0.7865    1.2926 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.7913   -1.7835   -0.3796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2100   -0.2865   -0.5919 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2560    0.0739    0.3992 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4575   -0.9024    0.2127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8569    1.3103    0.1416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1181    0.5866   -0.9375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1574   -0.3308   -1.7822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3882   -1.2540   -0.7263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3569    5.1702    0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0431    4.6712    0.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2940    4.4178    1.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4574    2.4028    0.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1787    1.6531    0.3394 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6425   -0.1299   -0.4332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6578   -2.3050   -1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2623   -2.6859   -0.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1321   -2.0068    1.6641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7836   -0.8818    2.2136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7210   -3.3364    0.3584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3040   -2.9718    1.8435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5832   -2.2227    0.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7149   -2.3123   -1.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8095   -0.4122   -1.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0098    0.0274    1.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4155   -0.3857    0.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3744   -1.3275   -0.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4044   -1.7225    0.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9870    1.8363    0.9913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4397    1.3194   -1.7601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7296   -0.8706   -2.5257 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6338    0.3309   -2.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7754   -2.1596   -1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  1
 15 16  1  0
 16 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 20 24  1  0
 24 25  1  0
 25 26  1  0
 24  5  1  0
 14  6  1  0
 26 14  1  0
 13  8  1  0
 26 17  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 19 39  1  0
 19 40  1  0
 20 41  1  6
 21 42  1  1
 22 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 24 47  1  6
 25 48  1  0
 25 49  1  0
 26 50  1  6
M  CHG  2  17   1  18  -1
M  END


  Mrv1652309102221522D          

 26 30  0  0  1  0            999 V2000
    1.4781    3.8783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4797    3.0533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1949    2.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086    3.0560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1965    1.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0003    1.4016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7602    1.7571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3466    1.1735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1713    1.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6027    0.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2094   -0.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3847   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9533    0.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0766    0.5160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2714   -0.3569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5881   -0.8612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8791   -0.3673    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.5359   -1.1175    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.0348   -0.1521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8011    0.7067    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0039    0.8875    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5629    0.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2497    1.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3921    1.3975    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7871    0.9265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2946    0.3105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  6 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
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  1  6  0  0  0
 20 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  6  0  0  0
 26 25  1  1  0  0  0
 14 26  1  0  0  0  0
 17 26  1  0  0  0  0
M  CHG  2  17   1  18  -1
M  END
> <DATABASE_ID>
NP0304632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C2NC3=CC=CC=C3C22CC[N+]3([O-])C[C@@H]([C@H](C)O)[C@@H]1C[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2O4/c1-11(23)13-10-22(25)8-7-20-14-5-3-4-6-15(14)21-18(20)17(19(24)26-2)12(13)9-16(20)22/h3-6,11-13,16,21,23H,7-10H2,1-2H3/t11-,12-,13-,16-,20?,22?/m0/s1

> <INCHI_KEY>
WSBPZWLQDOELJZ-REFLFHOCSA-N

> <FORMULA>
C20H24N2O4

> <MOLECULAR_WEIGHT>
356.422

> <EXACT_MASS>
356.173607261

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
37.85471263732974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(11S,12S,17S)-12-[(1S)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2,4,6,9-tetraen-14-ium-14-olate

> <JCHEM_LOGP>
-0.2892094593333341

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.103195026232743

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.661776590058896

> <JCHEM_PKA_STRONGEST_BASIC>
3.608768264679181

> <JCHEM_POLAR_SURFACE_AREA>
81.62

> <JCHEM_REFRACTIVITY>
99.5273

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(11S,12S,17S)-12-[(1S)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2,4,6,9-tetraen-14-ium-14-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       2.759   7.240   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.762   5.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.097   4.932   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.429   5.705   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.100   3.392   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.601   2.616   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       7.019   3.280   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       8.114   2.191   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.653   2.232   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.458   0.919   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.724  -0.435   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.185  -0.476   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.379   0.837   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.743   0.963   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.107  -0.666   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.831  -1.608   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       3.508  -0.686   0.000  0.00  0.00           N+1
HETATM   18  O   UNK     0       2.867  -2.086   0.000  0.00  0.00           O-1
HETATM   19  C   UNK     0       1.932  -0.284   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.495   1.319   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.007   1.657   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.051   0.524   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.466   3.127   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.599   2.609   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.336   1.729   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.283   0.580   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   24                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13    6   15   26                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   26                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   24                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   20    5   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   14   17                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄N₂O₄

Average Mass

356.4220 Da

Monoisotopic Mass

356.17361 Da

IUPAC Name

(11S,12S,17S)-12-[(1S)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2,4,6,9-tetraen-14-ium-14-olate

Traditional Name

(11S,12S,17S)-12-[(1S)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0^{1,9}.0^{2,7}.0^{14,17}]octadeca-2,4,6,9-tetraen-14-ium-14-olate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C2NC3=CC=CC=C3C22CC[N+]3([O-])C[C@@H]([C@H](C)O)[C@@H]1C[C@@H]23

InChI Identifier

InChI=1S/C20H24N2O4/c1-11(23)13-10-22(25)8-7-20-14-5-3-4-6-15(14)21-18(20)17(19(24)26-2)12(13)9-16(20)22/h3-6,11-13,16,21,23H,7-10H2,1-2H3/t11-,12-,13-,16-,20?,22?/m0/s1

InChI Key

WSBPZWLQDOELJZ-REFLFHOCSA-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 rostrata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as strychnos alkaloids. These are alkaloids having a core structure based on the strychnan, stemmadenine (seco-curan), or the akuammicine (curan) skeleton.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Strychnos alkaloids

Sub Class

Not Available

Direct Parent

Strychnos alkaloids

Alternative Parents

Substituents

Strychnan skeleton
Akuammicine-skeleton
Stemmadenine-skeleton
Carbazole
Indole or derivatives
Dihydroindole
Indolizidine
Secondary aliphatic/aromatic amine
Piperidine
N-alkylpyrrolidine
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Vinylogous amide
Trialkyl amine oxide
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
N-oxide
Carboxylic acid derivative
Trisubstituted n-oxide
Enamine
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Azacycle
Secondary amine
Organic oxide
Organic oxygen compound
Organic salt
Organic zwitterion
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Alcohol
Carbonyl group
Amine
Hydrocarbon derivative
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	-0.29	ChemAxon
pKa (Strongest Acidic)	13.66	ChemAxon
pKa (Strongest Basic)	3.61	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	81.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.53 m³·mol⁻¹	ChemAxon
Polarizability	37.85 Å³	ChemAxon
Number of Rings	5	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

C00043476

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

101678912

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Salim AA, Garson MJ, Craik DJ: New indole alkaloids from the bark of Alstonia scholaris. J Nat Prod. 2004 Sep;67(9):1591-4. doi: 10.1021/np0498612. [PubMed:15387668 ]
LOTUS database [Link]

Showing NP-Card for (11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate (NP0304632)

MOL for NP0304632 ((11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate)

3D MOL for NP0304632 ((11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate)

3D SDF for NP0304632 ((11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate)

3D-SDF for NP0304632 ((11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate)

PDB for NP0304632 ((11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate)

3D PDB for NP0304632 ((11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate)

SMILES for NP0304632 ((11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate)

INCHI for NP0304632 ((11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate)

Structure for NP0304632 ((11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate)

3D Structure for NP0304632 ((11s,12s,17s)-12-[(1s)-1-hydroxyethyl]-10-(methoxycarbonyl)-8,14-diazapentacyclo[9.5.2.0¹,⁹.0²,⁷.0¹⁴,¹⁷]octadeca-2,4,6,9-tetraen-14-ium-14-olate)