NP-MRD: Showing NP-Card for (15s,17s,19s)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate (NP0153291)

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Record Information

Version

2.0

Created at

2022-09-02 09:55:13 UTC

Updated at

2022-09-02 09:55:13 UTC

NP-MRD ID

NP0153291

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(15s,17s,19s)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate

Description

Vincamine N-oxide belongs to the class of organic compounds known as eburnan-type alkaloids. These are alkaloids with a structure based on the eburnan skeleton, that arises from rearrangement of the aspidospermidine ring system, involving migration of C-21 from C-7 to C-2, fission of the 2,16-bond, and attachment of C-16 to N-1. Based on a literature review very few articles have been published on Vincamine N-oxide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022211552D          

 27 31  0  0  1  0            999 V2000
    0.6869    0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106    0.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816   -0.1353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0579   -0.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053   -0.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763   -1.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999   -1.5619    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.3473   -2.2516    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1709   -2.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -2.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4472   -1.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762   -0.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289   -0.2296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521   -0.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913   -1.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0972   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640   -1.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.5073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9480    0.7447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0613    1.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226    1.8200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3035    1.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069    2.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    0.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526   -0.8721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  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  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  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
 11 19  1  0  0  0  0
 14 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 26  1  0  0  0  0
  3 26  1  0  0  0  0
 27 12  1  1  0  0  0
  3 27  1  0  0  0  0
  7 27  1  0  0  0  0
M  CHG  2   7   1   8  -1
M  END

     RDKit          3D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -1.8886    1.6048   -2.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3387    1.9280   -0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4165    1.2268    0.2456 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9587    1.6172    1.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8996    0.6570    2.2033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2989   -0.5232    1.3503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1100   -1.1016    0.8484 N   0  0  1  0  0  4  0  0  0  0  0  0
   -1.3309   -1.4232    1.9149 O   0  0  0  0  0  1  0  0  0  0  0  0
   -2.3118   -2.3520    0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0894   -2.9458   -0.4700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1162   -2.0920   -0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0346   -0.7376   -0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0874   -0.1419    0.1906 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0859   -1.0714    0.1246 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4602   -0.9847    0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2151   -2.1548    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6132   -3.3667   -0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2326   -3.4367   -0.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4677   -2.2917   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1362    1.2750    0.4726 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2117    1.4715    1.8824 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2947    1.9497   -0.0956 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1039    2.5663    0.6206 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5338    1.9269   -1.4548 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6488    2.5732   -2.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1091    1.9276    0.0236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4206   -0.2056   -0.0606 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6598    2.5366   -2.7804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6977    1.1066   -2.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085    0.9621   -2.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3667    1.5965   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2240    3.0299   -0.6609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4917    2.6142    1.5322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1206    1.8043    2.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8370    1.1586    2.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4551    0.2200    3.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7601   -1.2591    2.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0709   -0.2649    0.6006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8626   -3.0895    0.7824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0575   -2.1060   -0.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2625   -3.0868   -1.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8345   -3.9462   -0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9312   -0.0346    0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2859   -2.0701    0.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1997   -4.2642   -0.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7353   -4.3731   -0.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6635    0.7282    2.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4327    2.8063   -1.2803 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0748    1.8860   -2.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3225    3.4876   -2.5496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1754    2.9214    0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0399    2.2044   -1.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8007   -0.4632   -1.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 27  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 13 20  1  0
 20 21  1  1
 20 26  1  0
 20 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 27  3  1  0
 19 14  1  0
 26  3  1  0
 27  7  1  0
 19 11  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 27 53  1  6
 15 43  1  0
 16 44  1  0
 17 45  1  0
 18 46  1  0
 21 47  1  0
 26 51  1  0
 26 52  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
M  CHG  2   7   1   8  -1
M  END


  Mrv1652309022211552D          

 27 31  0  0  1  0            999 V2000
    0.6869    0.6488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5106    0.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816   -0.1353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0579   -0.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053   -0.7779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763   -1.5147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999   -1.5619    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.3473   -2.2516    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1709   -2.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946   -2.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4472   -1.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762   -0.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289   -0.2296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248   -0.4469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188   -0.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521   -0.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913   -1.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0972   -1.6491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640   -1.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.5073    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9480    0.7447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0613    1.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226    1.8200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3035    1.6526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2069    2.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    0.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526   -0.8721    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  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  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  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
 11 19  1  0  0  0  0
 14 19  1  0  0  0  0
 13 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 26  1  0  0  0  0
  3 26  1  0  0  0  0
 27 12  1  1  0  0  0
  3 27  1  0  0  0  0
  7 27  1  0  0  0  0
M  CHG  2   7   1   8  -1
M  END
> <DATABASE_ID>
NP0153291

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@]12CCC[N+]3([O-])CCC4=C([C@H]13)N(C1=CC=CC=C41)[C@](O)(C2)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O4/c1-3-20-10-6-11-23(26)12-9-15-14-7-4-5-8-16(14)22(17(15)18(20)23)21(25,13-20)19(24)27-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+,23?/m1/s1

> <INCHI_KEY>
YMNSBLFXXIFOLR-IMWDKWLZSA-N

> <FORMULA>
C21H26N2O4

> <MOLECULAR_WEIGHT>
370.449

> <EXACT_MASS>
370.189257325

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
40.29275375711106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(15S,17S,19S)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
2.2663751103333336

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.477920204275492

> <JCHEM_PKA_STRONGEST_BASIC>
3.1962017290161797

> <JCHEM_POLAR_SURFACE_AREA>
74.52

> <JCHEM_REFRACTIVITY>
101.61899999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(15S,17S,19S)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.282   1.211   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.820   1.123   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.512  -0.253   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.975  -0.164   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.130  -1.452   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.822  -2.827   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       3.360  -2.916   0.000  0.00  0.00           N+1
HETATM    8  O   UNK     0       2.515  -4.203   0.000  0.00  0.00           O-1
HETATM    9  C   UNK     0       4.052  -4.291   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.590  -4.379   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.435  -3.092   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.742  -1.716   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       6.587  -0.429   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       8.073  -0.834   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.368  -0.002   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.737  -0.707   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.810  -2.246   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.515  -3.078   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.146  -2.373   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.895   0.947   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.370   1.390   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.714   2.476   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.949   3.397   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.300   3.085   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.119   4.614   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.357   1.035   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.205  -1.628   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26   27                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   27                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11   13   27                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   11   14                                                  
CONECT   20   13   21   22   26                                             
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   20    3                                                       
CONECT   27   12    3    7                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆N₂O₄

Average Mass

370.4490 Da

Monoisotopic Mass

370.18926 Da

IUPAC Name

(15S,17S,19S)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate

Traditional Name

(15S,17S,19S)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate

CAS Registry Number

Not Available

SMILES

CC[C@@]12CCC[N+]3([O-])CCC4=C([C@H]13)N(C1=CC=CC=C41)[C@](O)(C2)C(=O)OC

InChI Identifier

InChI=1S/C21H26N2O4/c1-3-20-10-6-11-23(26)12-9-15-14-7-4-5-8-16(14)22(17(15)18(20)23)21(25,13-20)19(24)27-2/h4-5,7-8,18,25H,3,6,9-13H2,1-2H3/t18-,20+,21+,23?/m1/s1

InChI Key

YMNSBLFXXIFOLR-IMWDKWLZSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eburnan-type alkaloids. These are alkaloids with a structure based on the eburnan skeleton, that arises from rearrangement of the aspidospermidine ring system, involving migration of C-21 from C-7 to C-2, fission of the 2,16-bond, and attachment of C-16 to N-1.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Eburnan-type alkaloids

Sub Class

Not Available

Direct Parent

Eburnan-type alkaloids

Alternative Parents

Substituents

Eburna alkaloid
Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Naphthyridine
Alpha-amino acid or derivatives
3-alkylindole
Indole or derivatives
Indole
Piperidine
Benzenoid
Trialkyl amine oxide
Heteroaromatic compound
Methyl ester
Pyrrole
Carboxylic acid ester
Carboxylic acid derivative
Alkanolamine
Azacycle
N-oxide
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Trisubstituted n-oxide
Organic oxide
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Organic zwitterion
Carbonyl group
Organic oxygen compound
Organic salt
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	1.67	ALOGPS
logP	2.27	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	10.48	ChemAxon
pKa (Strongest Basic)	3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	101.62 m³·mol⁻¹	ChemAxon
Polarizability	40.29 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

Not Available

Chemspider ID

2303397

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3039951

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (15s,17s,19s)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate (NP0153291)

MOL for NP0153291 ((15s,17s,19s)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate)

3D MOL for NP0153291 ((15s,17s,19s)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate)

3D SDF for NP0153291 ((15s,17s,19s)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate)

3D-SDF for NP0153291 ((15s,17s,19s)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate)

PDB for NP0153291 ((15s,17s,19s)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate)

3D PDB for NP0153291 ((15s,17s,19s)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate)

SMILES for NP0153291 ((15s,17s,19s)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate)

INCHI for NP0153291 ((15s,17s,19s)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate)

Structure for NP0153291 ((15s,17s,19s)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate)

3D Structure for NP0153291 ((15s,17s,19s)-15-ethyl-17-hydroxy-17-(methoxycarbonyl)-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-11-ium-11-olate)