NP-MRD: Showing NP-Card for 14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine (NP0032626)

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Record Information

Version

2.0

Created at

2021-06-19 23:22:54 UTC

Updated at

2021-06-30 00:01:56 UTC

NP-MRD ID

NP0032626

Secondary Accession Numbers

None

Natural Product Identification

Common Name

14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine

Provided By

JEOL Database JEOL Logo

Description

14,15-Didehydro-10-hydroxy-11-methoxyvincamine 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. 14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine is found in E. officinalis and E. divaricata. 14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine was first documented in 2007 (PMID: 17253850). Based on a literature review very few articles have been published on 14,15-didehydro-10-hydroxy-11-methoxyvincamine.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101223D          

 55 59  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652306202101223D          

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    2.0226    0.4367    3.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2051   -0.9423    2.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958   -0.5099    4.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5097   -1.1711    3.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3018    0.0489    2.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0219   -1.6429    0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4755   -2.1815    1.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0405    1.2219   -3.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624   -0.0245   -6.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870    1.1015   -5.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383    0.4415   -4.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0777   -2.7337   -4.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5695   -2.7729   -1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1546    3.8525   -1.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083    1.5899    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1023   -0.1367    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2924    0.6314   -0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869    3.9734    0.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864    4.0924    0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1103    2.0222    1.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
 29 11  1  0  0  0  0
 21 20  2  0  0  0  0
 20 18  1  0  0  0  0
 10 11  2  0  0  0  0
 21 13  1  0  0  0  0
 18 15  2  0  0  0  0
 29  3  1  0  0  0  0
 11 12  1  0  0  0  0
 12 22  1  0  0  0  0
 22 28  1  0  0  0  0
 28  3  1  0  0  0  0
 10  9  1  0  0  0  0
 18 19  1  0  0  0  0
  7  8  1  0  0  0  0
 15 16  1  0  0  0  0
  8  9  1  0  0  0  0
 16 17  1  0  0  0  0
  7 29  1  0  0  0  0
  3  2  1  1  0  0  0
 13 12  1  0  0  0  0
  2  1  1  0  0  0  0
 15 14  1  0  0  0  0
 22 24  1  0  0  0  0
 14 13  2  0  0  0  0
 24 26  1  0  0  0  0
 10 21  1  0  0  0  0
 26 27  1  0  0  0  0
  7  6  1  0  0  0  0
 24 25  2  0  0  0  0
  3  4  1  0  0  0  0
 29 55  1  6  0  0  0
  4  5  2  0  0  0  0
 22 23  1  6  0  0  0
 14 43  1  0  0  0  0
 20 48  1  0  0  0  0
  8 39  1  0  0  0  0
  8 40  1  0  0  0  0
  9 41  1  0  0  0  0
  9 42  1  0  0  0  0
  4 35  1  0  0  0  0
  5 36  1  0  0  0  0
  6 37  1  0  0  0  0
  6 38  1  0  0  0  0
 28 53  1  0  0  0  0
 28 54  1  0  0  0  0
 19 47  1  0  0  0  0
 17 44  1  0  0  0  0
 17 45  1  0  0  0  0
 17 46  1  0  0  0  0
  2 33  1  0  0  0  0
  2 34  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 27 50  1  0  0  0  0
 27 51  1  0  0  0  0
 27 52  1  0  0  0  0
 23 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032626

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(OC([H])([H])[H])C([H])=C2N3C4=C(C2=C1[H])C([H])([H])C([H])([H])N1C([H])([H])C([H])=C([H])[C@@](C([H])([H])C([H])([H])[H])(C([H])([H])[C@@]3(O[H])C(=O)OC([H])([H])[H])[C@@]41[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O5/c1-4-21-7-5-8-23-9-6-13-14-10-16(25)17(28-2)11-15(14)24(18(13)19(21)23)22(27,12-21)20(26)29-3/h5,7,10-11,19,25,27H,4,6,8-9,12H2,1-3H3/t19-,21+,22-/m1/s1

> <INCHI_KEY>
UWXGHIWLXTUDQM-BAGYTPMASA-N

> <FORMULA>
C22H26N2O5

> <MOLECULAR_WEIGHT>
398.459

> <EXACT_MASS>
398.184171945

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
42.358215076846086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (15R,17R,19S)-15-ethyl-5,17-dihydroxy-4-methoxy-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18),13-pentaene-17-carboxylate

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
2.7234995096666674

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.546281345480198

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.356125784824963

> <JCHEM_PKA_STRONGEST_BASIC>
5.386922761920992

> <JCHEM_POLAR_SURFACE_AREA>
84.16000000000001

> <JCHEM_REFRACTIVITY>
108.98079999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.88e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (15R,17R,19S)-15-ethyl-5,17-dihydroxy-4-methoxy-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18),13-pentaene-17-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 59  0  0  0  0  0  0  0  0999 V2000
    0.1086    4.8602    3.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    3.6483    2.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0850    2.6343    1.9652 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1400    2.0517    2.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1261    0.8219    3.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0618   -0.0999    3.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258    0.5390    2.7541 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458   -0.4784    2.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725   -1.2960    1.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -0.4815    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8777    0.7827    0.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1123    1.2477   -0.6500 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1233    0.3214   -1.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4811    0.3486   -2.9562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248   -0.7649   -3.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8441   -0.8997   -5.0523 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5409    0.2254   -5.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078   -1.8665   -3.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5562   -2.9648   -4.1453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0074   -1.9001   -2.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8704   -0.7822   -1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6758    2.4747   -0.5603 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3809    3.2695   -1.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1928    2.1943   -0.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9881    2.9417   -1.1364 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5479    1.0807    0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9442    0.7869    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    3.3661    0.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1438    1.5163    1.6532 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4418    5.4841    4.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3362    5.4833    2.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479    4.5685    3.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170    3.1285    3.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6767    4.0238    2.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393    2.6564    2.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0226    0.4367    3.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2051   -0.9423    2.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958   -0.5099    4.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5097   -1.1711    3.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3018    0.0489    2.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0219   -1.6429    0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4755   -2.1815    1.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0405    1.2219   -3.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624   -0.0245   -6.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870    1.1015   -5.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383    0.4415   -4.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0777   -2.7337   -4.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5695   -2.7729   -1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1546    3.8525   -1.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083    1.5899    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1023   -0.1367    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2924    0.6314   -0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869    3.9734    0.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864    4.0924    0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1103    2.0222    1.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 29 11  1  0
 21 20  2  0
 20 18  1  0
 10 11  2  0
 21 13  1  0
 18 15  2  0
 29  3  1  0
 11 12  1  0
 12 22  1  0
 22 28  1  0
 28  3  1  0
 10  9  1  0
 18 19  1  0
  7  8  1  0
 15 16  1  0
  8  9  1  0
 16 17  1  0
  7 29  1  0
  3  2  1  1
 13 12  1  0
  2  1  1  0
 15 14  1  0
 22 24  1  0
 14 13  2  0
 24 26  1  0
 10 21  1  0
 26 27  1  0
  7  6  1  0
 24 25  2  0
  3  4  1  0
 29 55  1  6
  4  5  2  0
 22 23  1  6
 14 43  1  0
 20 48  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
  4 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
 28 53  1  0
 28 54  1  0
 19 47  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 27 50  1  0
 27 51  1  0
 27 52  1  0
 23 49  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       0.109   4.860   3.346  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.738   3.648   2.965  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.085   2.634   1.965  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.140   2.052   2.645  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.126   0.822   3.180  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.062  -0.100   3.152  0.00  0.00           C+0
HETATM    7  N   UNK     0      -1.326   0.539   2.754  0.00  0.00           N+0
HETATM    8  C   UNK     0      -2.346  -0.478   2.373  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.072  -1.296   1.073  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.323  -0.482   0.072  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.878   0.783   0.379  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.112   1.248  -0.650  0.00  0.00           N+0
HETATM   13  C   UNK     0      -0.123   0.321  -1.682  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.481   0.349  -2.956  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.325  -0.765  -3.787  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.844  -0.900  -5.052  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.541   0.225  -5.575  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.408  -1.867  -3.337  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.556  -2.965  -4.145  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.007  -1.900  -2.081  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.870  -0.782  -1.238  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.676   2.475  -0.560  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.381   3.269  -1.735  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.193   2.194  -0.566  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.988   2.942  -1.136  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.548   1.081   0.124  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.944   0.787   0.108  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.281   3.366   0.643  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.144   1.516   1.653  0.00  0.00           C+0
HETATM   30  H   UNK     0      -0.442   5.484   4.058  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.336   5.483   2.477  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.048   4.569   3.824  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.017   3.128   3.891  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.677   4.024   2.536  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.039   2.656   2.726  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.023   0.437   3.659  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.205  -0.942   2.503  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.196  -0.510   4.160  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.510  -1.171   3.208  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.302   0.049   2.249  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.022  -1.643   0.651  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.476  -2.182   1.323  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.040   1.222  -3.267  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.862  -0.025  -6.591  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.887   1.101  -5.640  0.00  0.00           H+0
HETATM   46  H   UNK     0       2.438   0.442  -4.986  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.078  -2.734  -4.965  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.569  -2.773  -1.767  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.155   3.853  -1.863  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.508   1.590   0.593  0.00  0.00           H+0
HETATM   51  H   UNK     0       4.102  -0.137   0.672  0.00  0.00           H+0
HETATM   52  H   UNK     0       4.292   0.631  -0.918  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.587   3.973   0.345  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.086   4.092   0.820  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.110   2.022   1.506  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    3    1   33   34                                             
CONECT    3   29   28    2    4                                             
CONECT    4    3    5   35                                                  
CONECT    5    6    4   36                                                  
CONECT    6    5    7   37   38                                             
CONECT    7    8   29    6                                                  
CONECT    8    7    9   39   40                                             
CONECT    9   10    8   41   42                                             
CONECT   10   11    9   21                                                  
CONECT   11   29   10   12                                                  
CONECT   12   11   22   13                                                  
CONECT   13   21   12   14                                                  
CONECT   14   15   13   43                                                  
CONECT   15   18   16   14                                                  
CONECT   16   15   17                                                       
CONECT   17   16   44   45   46                                             
CONECT   18   20   15   19                                                  
CONECT   19   18   47                                                       
CONECT   20   21   18   48                                                  
CONECT   21   20   13   10                                                  
CONECT   22   12   28   24   23                                             
CONECT   23   22   49                                                       
CONECT   24   22   26   25                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   50   51   52                                             
CONECT   28   22    3   53   54                                             
CONECT   29   11    3    7   55                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    2                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    6                                                            
CONECT   38    6                                                            
CONECT   39    8                                                            
CONECT   40    8                                                            
CONECT   41    9                                                            
CONECT   42    9                                                            
CONECT   43   14                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   17                                                            
CONECT   47   19                                                            
CONECT   48   20                                                            
CONECT   49   23                                                            
CONECT   50   27                                                            
CONECT   51   27                                                            
CONECT   52   27                                                            
CONECT   53   28                                                            
CONECT   54   28                                                            
CONECT   55   29                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  118    0
END

RDKit          3D

55 59  0  0  0  0  0  0  0  0999 V2000
    0.1086    4.8602    3.3459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381    3.6483    2.9650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0850    2.6343    1.9652 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1400    2.0517    2.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1261    0.8219    3.1804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0618   -0.0999    3.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258    0.5390    2.7541 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3458   -0.4784    2.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725   -1.2960    1.0732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235   -0.4815    0.0724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8777    0.7827    0.3792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1123    1.2477   -0.6500 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1233    0.3214   -1.6821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4811    0.3486   -2.9562 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3248   -0.7649   -3.7868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8441   -0.8997   -5.0523 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5409    0.2254   -5.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4078   -1.8665   -3.3372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5562   -2.9648   -4.1453 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0074   -1.9001   -2.0806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8704   -0.7822   -1.2377 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6758    2.4747   -0.5603 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3809    3.2695   -1.7354 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1928    2.1943   -0.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9881    2.9417   -1.1364 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5479    1.0807    0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9442    0.7869    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    3.3661    0.6433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1438    1.5163    1.6532 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4418    5.4841    4.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3362    5.4833    2.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479    4.5685    3.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170    3.1285    3.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6767    4.0238    2.5360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393    2.6564    2.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0226    0.4367    3.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2051   -0.9423    2.5028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1958   -0.5099    4.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5097   -1.1711    3.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3018    0.0489    2.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0219   -1.6429    0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4755   -2.1815    1.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0405    1.2219   -3.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8624   -0.0245   -6.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8870    1.1015   -5.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4383    0.4415   -4.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0777   -2.7337   -4.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5695   -2.7729   -1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1546    3.8525   -1.8631 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5083    1.5899    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1023   -0.1367    0.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2924    0.6314   -0.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5869    3.9734    0.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0864    4.0924    0.8200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1103    2.0222    1.5064 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 29 11  1  0
 21 20  2  0
 20 18  1  0
 10 11  2  0
 21 13  1  0
 18 15  2  0
 29  3  1  0
 11 12  1  0
 12 22  1  0
 22 28  1  0
 28  3  1  0
 10  9  1  0
 18 19  1  0
  7  8  1  0
 15 16  1  0
  8  9  1  0
 16 17  1  0
  7 29  1  0
  3  2  1  1
 13 12  1  0
  2  1  1  0
 15 14  1  0
 22 24  1  0
 14 13  2  0
 24 26  1  0
 10 21  1  0
 26 27  1  0
  7  6  1  0
 24 25  2  0
  3  4  1  0
 29 55  1  6
  4  5  2  0
 22 23  1  6
 14 43  1  0
 20 48  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
  9 42  1  0
  4 35  1  0
  5 36  1  0
  6 37  1  0
  6 38  1  0
 28 53  1  0
 28 54  1  0
 19 47  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 27 50  1  0
 27 51  1  0
 27 52  1  0
 23 49  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆N₂O₅

Average Mass

398.4590 Da

Monoisotopic Mass

398.18417 Da

IUPAC Name

methyl (15R,17R,19S)-15-ethyl-5,17-dihydroxy-4-methoxy-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18),13-pentaene-17-carboxylate

Traditional Name

methyl (15R,17R,19S)-15-ethyl-5,17-dihydroxy-4-methoxy-1,11-diazapentacyclo[9.6.2.0^{2,7}.0^{8,18}.0^{15,19}]nonadeca-2,4,6,8(18),13-pentaene-17-carboxylate

CAS Registry Number

Not Available

SMILES

[H]OC1=C(OC([H])([H])[H])C([H])=C2N3C4=C(C2=C1[H])C([H])([H])C([H])([H])N1C([H])([H])C([H])=C([H])[C@@](C([H])([H])C([H])([H])[H])(C([H])([H])[C@@]3(O[H])C(=O)OC([H])([H])[H])[C@@]41[H]

InChI Identifier

InChI=1S/C22H26N2O5/c1-4-21-7-5-8-23-9-6-13-14-10-16(25)17(28-2)11-15(14)24(18(13)19(21)23)22(27,12-21)20(26)29-3/h5,7,10-11,19,25,27H,4,6,8-9,12H2,1-3H3/t19-,21+,22-/m1/s1

InChI Key

UWXGHIWLXTUDQM-BAGYTPMASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Emblica officinalis	JEOL database	Zhang, H., et al, J. Nat. Prod. 70, 54 (2007)
Eurybia divaricata	JEOL database	Zhang, H., et al, J. Nat. Prod. 70, 54 (2007)

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
Alpha-amino acid or derivatives
Hydroxyindole
Naphthyridine
3-alkylindole
Indole
Indole or derivatives
Anisole
Phenol ether
Aralkylamine
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Methyl ester
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Monocarboxylic acid or derivatives
Alkanolamine
Ether
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Amine
Organic nitrogen compound
Organonitrogen compound
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	2.18	ALOGPS
logP	2.72	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.36	ChemAxon
pKa (Strongest Basic)	5.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.16 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	108.98 m³·mol⁻¹	ChemAxon
Polarizability	42.36 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

17262734

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16104888

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang H, Wang XN, Lin LP, Ding J, Yue JM: Indole alkaloids from three species of the Ervatamia genus: E. officinalis, E. divaricata, and E. divaricata Gouyahua. J Nat Prod. 2007 Jan;70(1):54-9. doi: 10.1021/np060344o. [PubMed:17253850 ]
Zhang, H., et al. (2007). Zhang, H., et al, J. Nat. Prod. 70, 54 (2007) . J. Nat. Prod..

Showing NP-Card for 14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine (NP0032626)

MOL for NP0032626 (14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine)

3D MOL for NP0032626 (14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine)

3D SDF for NP0032626 (14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine)

3D-SDF for NP0032626 (14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine)

PDB for NP0032626 (14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine)

3D PDB for NP0032626 (14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine)

SMILES for NP0032626 (14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine)

INCHI for NP0032626 (14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine)

Structure for NP0032626 (14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine)

3D Structure for NP0032626 (14,15-didehydro-10-hydroxy-11-methoxy-16-epivincamine)