NP-MRD: Showing NP-Card for Leurosine (NP0050882)

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Record Information

Version

2.0

Created at

2022-04-27 22:20:10 UTC

Updated at

2022-04-27 22:20:11 UTC

NP-MRD ID

NP0050882

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Leurosine

Description

Methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19S)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-10-(methoxycarbonyl)-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Nonadeca-2,4,6,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0⁴,¹².0⁵,¹⁰.0¹⁶,¹⁸]Icosa-4(12),5,7,9-tetraene-13-carboxylate belongs to the class of organic compounds known as vinca alkaloids. These are alkaloids with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together. Leurosine is found in Catharanthus lanceus, Catharanthus longifolius, Catharanthus ovalis, Catharanthus pusillus, Catharanthus roseus and Catharanthus spp.. Based on a literature review very few articles have been published on methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19S)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-10-(methoxycarbonyl)-8-methyl-8,16-diazapentacyclo[10.6.1.0¹,⁹.0²,⁷.0¹⁶,¹⁹]Nonadeca-2,4,6,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0⁴,¹².0⁵,¹⁰.0¹⁶,¹⁸]Icosa-4(12),5,7,9-tetraene-13-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200202D          

 59 68  0  0  1  0            999 V2000
   11.7717   -4.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2257   -3.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4171   -3.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1545   -4.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7005   -5.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5091   -4.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3295   -4.4876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0822   -3.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7544   -3.2222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3629   -3.2582    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5159   -3.4047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8994   -4.0187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1975   -4.7232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3559   -5.4717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2128   -5.6228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9914   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5106   -5.6951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8746   -5.1389    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0734   -4.3382    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2806   -4.5664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167   -5.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5114   -5.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1502   -2.4611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7342   -1.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5215   -1.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7249   -0.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1409   -1.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3536   -2.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4062   -1.0743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5361   -0.2596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3511   -0.1314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7264    0.6033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8955    0.2602    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1250   -0.0346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9951   -0.8493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6357   -1.3692    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5058   -2.1839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7353   -2.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0947   -1.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2246   -1.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4747   -2.4075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9247   -1.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3545   -0.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2800   -0.7978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4844    0.4853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7139    0.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0733    0.7103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5840   -0.6243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3927    0.9186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6277    1.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8181    1.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1697    1.6626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9019    2.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5309   -2.0928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1149   -1.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8562   -2.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0378   -1.7922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6755   -2.6935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1688   -2.0322    0.0000 C   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  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  7 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  6  0  0  0
 18 20  1  0  0  0  0
 18 21  1  1  0  0  0
 21 22  1  0  0  0  0
 10 23  1  6  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 29 27  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  6  0  0  0
 26 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 29 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
 37 41  1  0  0  0  0
 41 42  1  0  0  0  0
 29 42  1  0  0  0  0
 35 43  1  6  0  0  0
 43 44  1  0  0  0  0
 34 45  1  1  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 33 49  1  1  0  0  0
 33 50  1  6  0  0  0
 50 51  2  0  0  0  0
 50 52  1  0  0  0  0
 52 53  1  0  0  0  0
 24 54  1  0  0  0  0
 54 55  1  0  0  0  0
 10 56  1  1  0  0  0
 56 57  2  0  0  0  0
 56 58  1  0  0  0  0
 58 59  1  0  0  0  0
M  END

     RDKit          3D

115124  0  0  0  0  0  0  0  0999 V2000
    4.8083    3.0691    5.3046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7320    2.0238    5.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6152    1.4320    3.9072 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8345    0.7530    3.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9358    1.0292    1.9625 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5992    0.2445    1.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3378   -1.2130    0.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4954   -1.6528   -0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3201   -1.2381   -0.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0691   -3.8270   -3.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2020   -4.6111   -3.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1873   -4.4621   -2.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0158   -3.5079   -1.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8892   -2.6819   -1.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3517   -0.1890   -0.1540 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3757    0.8206   -1.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5439    2.0414   -1.1186 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1954    0.4248   -2.5859 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1692   -2.7269    1.4246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7080    0.8451   -0.1726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8083    1.6173   -0.6182 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7212    2.2415    0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8597    3.0409   -0.3619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5661    2.1171    1.4412 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4570    1.6326   -0.4796 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5407    1.7165    0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3329    2.5906    0.5037 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8400    2.6203    5.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7760    3.7093    6.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9502    1.2453    6.0562 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8049   -0.3048    3.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7215    1.1815    3.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3351    0.6424    0.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6972    0.5255    1.1029 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3964   -1.6522    0.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1185   -1.9056   -2.3364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2892   -3.9387   -3.7671 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7899    0.8801    0.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
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 58115  1  1
M  END


  Mrv1652304282200202D          

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 58 59  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050882

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@]12CN3C[C@@H](C[C@@](C(=O)OC)(C4=C(CC3)C3=CC=CC=C3N4)C3=C(OC)C=C4N(C)[C@@H]5[C@]6(CCN7CC=C[C@](CC)([C@H]67)[C@@H](OC(C)=O)[C@]5(O)C(=O)OC)C4=C3)[C@H]1O2

> <INCHI_IDENTIFIER>
InChI=1S/C46H56N4O9/c1-8-42-16-12-18-50-20-17-44(37(42)50)30-21-31(34(55-5)22-33(30)48(4)38(44)46(54,41(53)57-7)39(42)58-26(3)51)45(40(52)56-6)23-27-24-49(25-43(9-2)36(27)59-43)19-15-29-28-13-10-11-14-32(28)47-35(29)45/h10-14,16,21-22,27,36-39,47,54H,8-9,15,17-20,23-25H2,1-7H3/t27-,36-,37-,38-,39-,42-,43+,44-,45+,46+/m1/s1

> <INCHI_KEY>
LPGWZGMPDKDHEP-GKWAKPNHSA-N

> <FORMULA>
C46H56N4O9

> <MOLECULAR_WEIGHT>
808.973

> <EXACT_MASS>
808.404729399

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
115

> <JCHEM_AVERAGE_POLARIZABILITY>
85.91696354152816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19S)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-10-(methoxycarbonyl)-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0^{4,12}.0^{5,10}.0^{16,18}]icosa-4(12),5,7,9-tetraene-13-carboxylate

> <ALOGPS_LOGP>
4.18

> <JCHEM_LOGP>
4.311501980333335

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
16.30973521730559

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.86801224566425

> <JCHEM_PKA_STRONGEST_BASIC>
8.654569451316204

> <JCHEM_POLAR_SURFACE_AREA>
146.4

> <JCHEM_REFRACTIVITY>
220.17319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.92e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19S)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-10-(methoxycarbonyl)-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0^{4,12}.0^{5,10}.0^{16,18}]icosa-4(12),5,7,9-tetraene-13-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      21.974  -7.781   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.955  -6.626   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      19.445  -6.932   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.955  -8.392   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.974  -9.546   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.484  -9.241   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.415  -8.377   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.954  -6.908   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      18.208  -6.015   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      15.611  -6.082   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.030  -6.355   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.879  -7.501   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.435  -8.817   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      13.731 -10.214   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      15.331 -10.496   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.784  -9.816   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.153 -10.631   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.966  -9.593   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.337  -8.098   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.857  -8.524   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.924 -10.727   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.421 -10.392   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.214  -4.594   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.304  -3.506   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.907  -2.018   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.420  -1.618   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.330  -2.706   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.727  -4.194   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.958  -2.005   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.201  -0.485   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      13.722  -0.245   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0      14.423   1.126   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.005   0.486   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.567  -0.065   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.324  -1.585   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.520  -2.556   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0      10.277  -4.077   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0       8.839  -4.627   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.643  -3.657   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.886  -2.136   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      12.086  -4.494   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      12.926  -3.203   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.128  -0.615   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.123  -1.489   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       8.371   0.906   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       6.933   0.355   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       5.737   1.326   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       6.690  -1.165   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      11.933   1.715   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      10.505   1.942   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       8.994   2.238   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      11.517   3.104   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      11.017   4.560   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      17.791  -3.906   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      18.881  -2.819   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      16.532  -4.848   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      16.871  -3.345   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      18.061  -5.028   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      18.982  -3.793   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8   16                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   23   56                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15    7                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18   12   20                                                  
CONECT   20   19   18                                                       
CONECT   21   18   22                                                       
CONECT   22   21                                                            
CONECT   23   10   24   28                                                  
CONECT   24   23   25   54                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27   30   36   42                                             
CONECT   30   29   31   33                                                  
CONECT   31   30   26   32                                                  
CONECT   32   31                                                            
CONECT   33   30   34   49   50                                             
CONECT   34   33   35   45                                                  
CONECT   35   34   36   40   43                                             
CONECT   36   35   29   37                                                  
CONECT   37   36   38   41                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
CONECT   41   37   42                                                       
CONECT   42   41   29                                                       
CONECT   43   35   44                                                       
CONECT   44   43                                                            
CONECT   45   34   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   33                                                            
CONECT   50   33   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   53                                                       
CONECT   53   52                                                            
CONECT   54   24   55                                                       
CONECT   55   54                                                            
CONECT   56   10   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59                                                       
CONECT   59   58                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  136    0
END

View in JSmol

Synonyms

Value	Source
Methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19S)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-10-(methoxycarbonyl)-8-methyl-8,16-diazapentacyclo[10.6.1.0,.0,.0,]nonadeca-2,4,6,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0,.0,.0,]icosa-4(12),5,7,9-tetraene-13-carboxylic acid	Generator

Chemical Formula

C₄₆H₅₆N₄O₉

Average Mass

808.9730 Da

Monoisotopic Mass

808.40473 Da

IUPAC Name

methyl (13S,15R,16R,18S)-13-[(1R,9R,10S,11R,12R,19S)-11-(acetyloxy)-12-ethyl-10-hydroxy-5-methoxy-10-(methoxycarbonyl)-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraen-4-yl]-18-ethyl-17-oxa-1,11-diazapentacyclo[13.4.1.0^{4,12}.0^{5,10}.0^{16,18}]icosa-4(12),5,7,9-tetraene-13-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@]12CN3C[C@@H](C[C@@](C(=O)OC)(C4=C(CC3)C3=CC=CC=C3N4)C3=C(OC)C=C4N(C)[C@@H]5[C@]6(CCN7CC=C[C@](CC)([C@H]67)[C@@H](OC(C)=O)[C@]5(O)C(=O)OC)C4=C3)[C@H]1O2

InChI Identifier

InChI=1S/C46H56N4O9/c1-8-42-16-12-18-50-20-17-44(37(42)50)30-21-31(34(55-5)22-33(30)48(4)38(44)46(54,41(53)57-7)39(42)58-26(3)51)45(40(52)56-6)23-27-24-49(25-43(9-2)36(27)59-43)19-15-29-28-13-10-11-14-32(28)47-35(29)45/h10-14,16,21-22,27,36-39,47,54H,8-9,15,17-20,23-25H2,1-7H3/t27-,36-,37-,38-,39-,42-,43+,44-,45+,46+/m1/s1

InChI Key

LPGWZGMPDKDHEP-GKWAKPNHSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Catharanthus lanceus	Plant	KNApSAcK
Catharanthus longifolius	Plant	KNApSAcK
Catharanthus ovalis	Plant	KNApSAcK
Catharanthus pusillus	Plant	KNApSAcK
Catharanthus roseus	Plant	KNApSAcK
Catharanthus spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vinca alkaloids. These are alkaloids with a dimeric chemical structure composed of an indole nucleus (catharanthine), and a dihydroindole nucleus (vindoline), joined together.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Vinca alkaloids

Sub Class

Not Available

Direct Parent

Vinca alkaloids

Alternative Parents

Substituents

Vinca alkaloid skeleton
Carbazole
3-alkylindole
Tricarboxylic acid or derivatives
Indole or derivatives
Indole
Dialkylarylamine
Tertiary aliphatic/aromatic amine
Anisole
Aralkylamine
Epoxypiperidine
Alkyl aryl ether
Para-oxazepine
Benzenoid
N-alkylpyrrolidine
Piperidine
Heteroaromatic compound
Methyl ester
Tertiary alcohol
Pyrrolidine
Pyrrole
Cyclic alcohol
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	4.18	ALOGPS
logP	4.31	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	10.87	ChemAxon
pKa (Strongest Basic)	8.65	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	146.4 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	220.17 m³·mol⁻¹	ChemAxon
Polarizability	85.92 Å³	ChemAxon
Number of Rings	10	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

12814305

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Leurosine (NP0050882)

MOL for NP0050882 (Leurosine)

3D MOL for NP0050882 (Leurosine)

3D SDF for NP0050882 (Leurosine)

3D-SDF for NP0050882 (Leurosine)

PDB for NP0050882 (Leurosine)

3D PDB for NP0050882 (Leurosine)

SMILES for NP0050882 (Leurosine)

INCHI for NP0050882 (Leurosine)

Structure for NP0050882 (Leurosine)

3D Structure for NP0050882 (Leurosine)