NP-MRD: Showing NP-Card for Voacamine (NP0050921)

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Record Information

Version

2.0

Created at

2022-04-27 22:23:15 UTC

Updated at

2022-04-27 22:23:15 UTC

NP-MRD ID

NP0050921

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Voacamine

Description

Voacamine is found in Tabernaemontana divaricata, family Apocynaceae spp., Hedranthera barteri, Peschiera lacta, Tabernaemontana arborea , Tabernaemontana australis, Tabernaemontana hystrix, Tabernaemontana laeta, Tabernaemontana oppositifolia, Tabernaemontana pachysiphon , Tabernaemontana solanifolia, Tabernaemontana vanheurckii, Voacanga africana , Voacanga globosa, Voacanga grandiflora, Voacanga papuana, Voacanga schweinfurthii and Voacanga thouarsii.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200232D          

 52 60  0  0  1  0            999 V2000
    6.1014   -4.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6096   -3.7328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9374   -2.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7569   -2.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2487   -3.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9210   -4.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9201   -2.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2013   -1.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940   -2.2256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9913   -0.8409    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4603   -0.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2971    0.1244    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6987   -0.5190    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2069   -1.0820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    8.8743   -0.5296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0116    0.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1775   -0.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8884    0.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0747    0.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5501   -0.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1937   -1.7194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5056   -1.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4008    0.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3979   -2.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  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
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 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 14 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 16 21  1  0  0  0  0
 13 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 10 26  1  1  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 29 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
 37 36  1  6  0  0  0
 37 38  1  0  0  0  0
 32 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 37 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 40 45  1  0  0  0  0
 36 45  1  0  0  0  0
 38 46  1  6  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 30 50  2  0  0  0  0
 26 50  1  0  0  0  0
 27 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END

     RDKit          3D

104112  0  0  0  0  0  0  0  0999 V2000
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  2  1  1  0
 48 49  1  0
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  3 47  1  0
 17  9  1  0
 38 89  1  0
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 31 80  1  0
 30 77  1  0
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 22 72  1  0
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 18 70  1  1
 46 98  1  0
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 47100  1  6
 48101  1  6
  7 62  1  6
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  6 59  1  0
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  4 57  1  0
  4 58  1  0
  2 56  1  0
  1 53  1  0
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  1 55  1  0
 52102  1  0
 52103  1  0
 52104  1  0
 29 74  1  0
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 26 73  1  0
 45 96  1  0
 45 97  1  0
 39 92  1  1
 44 93  1  0
 44 94  1  0
 44 95  1  0
M  END


  Mrv1652304282200232D          

 52 60  0  0  1  0            999 V2000
    6.1014   -4.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6096   -3.7328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9374   -2.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7569   -2.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2487   -3.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9210   -4.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9201   -2.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2013   -1.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5940   -2.2256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9913   -0.8409    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4603   -0.1251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2971    0.1244    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6987   -0.5190    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2069   -1.0820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7372   -1.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8743   -0.5296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8013    0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0116    0.6143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9838    1.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3943    2.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6995   -0.7693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3138   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6662   -0.7302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4545   -2.2432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4284   -2.1925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1775   -0.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8884    0.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0747    0.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5501   -0.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8392   -1.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1937   -1.7194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5056   -1.2642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7259   -0.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2658    0.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4008    0.4423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7068   -0.1659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9655   -1.2101    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7126   -1.4820    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9149   -0.6775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0632   -0.0024    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1333   -0.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2311   -1.3810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3979   -2.1711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2678   -2.1827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6643   -0.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2606   -2.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4184   -2.1298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4246   -3.1331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9911   -3.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6529   -1.3416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9777    0.9593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6776    1.8000    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  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 14 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  6  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 16 21  1  0  0  0  0
 13 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 10 26  1  1  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 29 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
 37 36  1  6  0  0  0
 37 38  1  0  0  0  0
 32 38  1  0  0  0  0
 38 39  1  0  0  0  0
 40 39  1  6  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 37 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  0  0  0  0
 40 45  1  0  0  0  0
 36 45  1  0  0  0  0
 38 46  1  6  0  0  0
 46 47  2  0  0  0  0
 46 48  1  0  0  0  0
 48 49  1  0  0  0  0
 30 50  2  0  0  0  0
 26 50  1  0  0  0  0
 27 51  1  0  0  0  0
 51 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050921

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1C[C@H]2CN3CCC4=C(NC5=CC([C@H]6C[C@H]7[C@@H]([C@@H](CC8=C6NC6=CC=CC=C86)N(C)C\C7=C\C)C(=O)OC)=C(OC)C=C45)[C@](C2)([C@H]13)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/b25-8-/t23-,24+,28-,31-,35-,37+,40+,43-/m1/s1

> <INCHI_KEY>
VCMIRXRRQJNZJT-BJRZNXPRSA-N

> <FORMULA>
C43H52N4O5

> <MOLECULAR_WEIGHT>
704.912

> <EXACT_MASS>
704.39377079

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
104

> <JCHEM_AVERAGE_POLARIZABILITY>
80.28129191135446

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,15R,17S,18S)-17-ethyl-6-[(1R,12R,14S,15E,18S)-15-ethylidene-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

> <ALOGPS_LOGP>
6.26

> <JCHEM_LOGP>
6.20619741

> <ALOGPS_LOGS>
-5.34

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
16.779474717636717

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.555075374646346

> <JCHEM_PKA_STRONGEST_BASIC>
8.525647764336558

> <JCHEM_POLAR_SURFACE_AREA>
99.89000000000001

> <JCHEM_REFRACTIVITY>
203.68439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,15R,17S,18S)-17-ethyl-6-[(1R,12R,14S,15E,18S)-15-ethylidene-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-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      11.389  -8.204   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.471  -6.968   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.083  -5.555   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.613  -5.378   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.531  -6.614   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.919  -8.028   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.917  -3.868   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.576  -3.112   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      10.442  -4.154   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      11.184  -1.570   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.059  -0.233   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.621   0.232   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.371  -0.969   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.320  -2.020   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.443  -3.393   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      16.565  -0.989   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      16.429   0.584   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.955   1.147   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.903   2.776   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.803   3.919   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.106  -1.436   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.652  -2.411   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.444  -1.363   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      13.915  -4.187   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      15.733  -4.093   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.665  -1.316   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.125   0.127   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.606   0.380   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.627  -0.808   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.167  -2.251   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       5.962  -3.209   0.000  0.00  0.00           N+0
HETATM   32  C   UNK     0       4.677  -2.360   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.088  -0.876   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.229   0.514   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.615   0.826   0.000  0.00  0.00           C+0
HETATM   36  N   UNK     0       1.319  -0.310   0.000  0.00  0.00           N+0
HETATM   37  C   UNK     0       1.802  -2.259   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.197  -2.766   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.574  -1.265   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.985  -0.004   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       0.249  -1.028   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       0.431  -2.578   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.743  -4.053   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -2.367  -4.074   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       3.107  -0.193   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       2.353  -4.255   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       0.781  -3.976   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       2.659  -5.849   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       1.850  -7.213   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.685  -2.504   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       9.292   1.791   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       8.731   3.360   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   15                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14   22                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14    7                                                       
CONECT   16   14   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   16                                                            
CONECT   22   13   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   10   27   50                                                  
CONECT   27   26   28   51                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   33                                                  
CONECT   30   29   31   50                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   38                                                  
CONECT   33   32   29   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   45                                                  
CONECT   37   36   38   42                                                  
CONECT   38   37   32   39   46                                             
CONECT   39   38   40                                                       
CONECT   40   39   41   45                                                  
CONECT   41   40   42                                                       
CONECT   42   41   37   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43                                                            
CONECT   45   40   36                                                       
CONECT   46   38   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49                                                       
CONECT   49   48                                                            
CONECT   50   30   26                                                       
CONECT   51   27   52                                                       
CONECT   52   51                                                            
MASTER        0    0    0    0    0    0    0    0   52    0  120    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₃H₅₂N₄O₅

Average Mass

704.9120 Da

Monoisotopic Mass

704.39377 Da

IUPAC Name

methyl (1S,15R,17S,18S)-17-ethyl-6-[(1R,12R,14S,15E,18S)-15-ethylidene-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.0^{2,10}.0^{4,9}.0^{13,18}]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC[C@H]1C[C@H]2CN3CCC4=C(NC5=CC([C@H]6C[C@H]7[C@@H]([C@@H](CC8=C6NC6=CC=CC=C86)N(C)C\C7=C\C)C(=O)OC)=C(OC)C=C45)[C@](C2)([C@H]13)C(=O)OC

InChI Identifier

InChI=1S/C43H52N4O5/c1-7-24-15-23-20-43(42(49)52-6)39-27(13-14-47(21-23)40(24)43)29-19-36(50-4)30(17-34(29)45-39)31-16-28-25(8-2)22-46(3)35(37(28)41(48)51-5)18-32-26-11-9-10-12-33(26)44-38(31)32/h8-12,17,19,23-24,28,31,35,37,40,44-45H,7,13-16,18,20-22H2,1-6H3/b25-8-/t23-,24+,28-,31-,35-,37+,40+,43-/m1/s1

InChI Key

VCMIRXRRQJNZJT-BJRZNXPRSA-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
Ervatamia coronaria	LOTUS Database	35616633
family Apocynaceae spp.	-	KNApSAcK
Hedranthera barteri	Plant	KNApSAcK
Peschiera lacta	Plant	KNApSAcK
Tabernaemontana arborea	Plant	KNApSAcK
Tabernaemontana australis	Plant	KNApSAcK
Tabernaemontana hystrix	LOTUS Database	35616633
Tabernaemontana laeta Mart.	LOTUS Database	35616633
Tabernaemontana oppositifolia	Plant	KNApSAcK
Tabernaemontana pachysiphon	Plant	KNApSAcK
Tabernaemontana solanifolia	LOTUS Database	35616633
Tabernaemontana vanheurckii	LOTUS Database	35616633
Voacanga africana	Plant	KNApSAcK
Voacanga globosa	Plant	KNApSAcK
Voacanga grandiflora	Plant	KNApSAcK
Voacanga papuana	Plant	KNApSAcK
Voacanga schweinfurthii	LOTUS Database	35616633
Voacanga thouarsii	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	6.26	ALOGPS
logP	6.21	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	15.56	ChemAxon
pKa (Strongest Basic)	8.53	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	99.89 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	203.68 m³·mol⁻¹	ChemAxon
Polarizability	80.28 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for Voacamine (NP0050921)

MOL for NP0050921 (Voacamine)

3D MOL for NP0050921 (Voacamine)

3D SDF for NP0050921 (Voacamine)

3D-SDF for NP0050921 (Voacamine)

PDB for NP0050921 (Voacamine)

3D PDB for NP0050921 (Voacamine)

SMILES for NP0050921 (Voacamine)

INCHI for NP0050921 (Voacamine)

Structure for NP0050921 (Voacamine)

3D Structure for NP0050921 (Voacamine)