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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References transporters (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:02 UTC

HMDB ID

HMDB0015597

Secondary Accession Numbers

HMDB15597

Metabolite Identification

Common Name

Voacamine

Description

Voacamine is only found in individuals that have used or taken this drug. It is an alkaloid isolated from the bark of the Pescheria fuchsiae folia tree. It is an antimalarial drug approved for use in several African countries. Voacamine is also under investigation for use in modulating multidrug-resistance in tumor cells. Voacamine is possibly a substrate for P-glycoprotein (P-gp), an efflux pump responsible for multidrug resistance in tumor cells. Voacamine may compete with anticancer drugs such as doxorubicin for P-gp transport, decreasing removal of doxorubicin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02231217582D          

 57 65  0  0  1  0            999 V2000
    9.0528    0.3907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6240    0.9931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4478    0.5035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2480   -2.4864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8056   -3.5114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3008    3.2056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7761    0.5858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3110   -2.9732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5432   -1.5194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8152    2.5605    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6315    1.7562    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0755    1.4090    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.6323    2.8265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2524    1.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2668    2.2468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7067    2.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8883    1.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4758    3.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8066    3.6328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1449    1.7562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4480    0.9519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9614    2.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5797    1.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9690    0.4401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5921    3.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7264    1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5318   -0.2938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6778   -0.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2474   -0.9794    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7654   -1.3368    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2723    0.4764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4324   -0.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6372   -2.1518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1228   -2.8187    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8692   -0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7330   -1.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9377   -2.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9725   -1.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6047   -2.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7514   -2.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3368   -2.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0392   -2.7201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9156   -2.2501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4785   -3.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3850   -0.9899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5467   -3.6591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0589    1.2312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7445   -2.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5928   -0.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3705   -3.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9734   -3.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.0548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9620    3.2040    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2424    0.7705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5112   -3.3522    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  1 35  1  0  0  0  0
  2 21  2  0  0  0  0
  3 31  1  0  0  0  0
  3 47  1  0  0  0  0
  4 42  1  0  0  0  0
  4 52  1  0  0  0  0
  5 42  2  0  0  0  0
  6 10  1  0  0  0  0
  6 16  1  0  0  0  0
  6 18  1  0  0  0  0
  7 17  1  0  0  0  0
  7 24  1  0  0  0  0
  8 34  1  0  0  0  0
  8 40  1  0  0  0  0
  8 44  1  0  0  0  0
  9 36  1  0  0  0  0
  9 43  1  0  0  0  0
 10 11  1  0  0  0  0
 10 13  1  0  0  0  0
 10 53  1  6  0  0  0
 11 14  1  0  0  0  0
 11 17  1  0  0  0  0
 11 21  1  6  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 12 16  1  0  0  0  0
 12 54  1  6  0  0  0
 13 15  1  0  0  0  0
 13 19  1  1  0  0  0
 17 20  2  0  0  0  0
 18 22  1  0  0  0  0
 19 25  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 26  2  0  0  0  0
 24 27  2  0  0  0  0
 26 31  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 31  2  0  0  0  0
 29 32  1  0  0  0  0
 29 36  1  0  0  0  0
 29 55  1  1  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 30 38  1  0  0  0  0
 30 56  1  1  0  0  0
 33 34  1  0  0  0  0
 33 42  1  0  0  0  0
 34 37  1  0  0  0  0
 34 57  1  6  0  0  0
 36 39  2  0  0  0  0
 37 39  1  0  0  0  0
 38 40  1  0  0  0  0
 38 45  2  0  0  0  0
 39 41  1  0  0  0  0
 41 43  1  0  0  0  0
 41 46  2  0  0  0  0
 43 48  2  0  0  0  0
 45 49  1  0  0  0  0
 46 50  1  0  0  0  0
 48 51  1  0  0  0  0
 50 51  2  0  0  0  0
M  END

HMDB0015597
     RDKit          3D
Voacamine
104112  0  0  0  0  0  0  0  0999 V2000
   -3.6885    4.0783    0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3274    2.8680    1.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4407    1.7447    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0775    0.5101    1.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9547   -0.1714    0.2137 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4928   -1.4253    0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4771   -0.2929   -1.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4320   -1.3146   -1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5294   -1.8360   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6151   -1.2082    0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9982   -2.1158    1.2523 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4819   -3.3666    1.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1644   -4.6116    1.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8893   -5.6971    1.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8818   -5.5703    0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2001   -4.3581   -0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4770   -3.2475    0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3074    0.2761    0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8159    0.4503    0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0732   -0.1003   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4314    0.0823    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5545   -0.3074   -0.6525 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922    0.1068    0.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3251    0.7957    1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8590    0.7975    1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9523    1.3512    2.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3947    1.1568    1.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3257    1.6719    2.6218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420    2.3901    3.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1343    1.5087    2.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3782    2.1111    1.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2999    1.1329    1.0582 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5262   -0.0281    1.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7567   -1.2615    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8928   -0.9546    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4544    0.1934   -0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5225    1.2888   -0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8092    0.7447   -1.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1306    0.7601   -0.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0432   -0.2829   -0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962   -0.5986   -1.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0132   -1.7371   -2.3478 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6355    0.3848   -2.8358 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5069    0.0076   -4.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4791   -1.5605    0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6478    0.9035   -0.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9451    1.6345   -0.8986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0783    1.0877   -1.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2591    2.0243   -1.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1822    3.0559   -0.9931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3954    1.7119   -2.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4906    2.6601   -2.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639    3.8407    0.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.8370   -1.2761    1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3285   -1.7475    0.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3639   -0.5796   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9456   -2.2020   -1.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8033   -0.9610   -2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3190   -1.9002    1.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -4.7240    2.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6727   -6.6770    1.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4235   -6.4508   -0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9737   -4.2691   -1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8132    0.7555    1.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2694   -0.6462   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5643   -0.8026   -1.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2810    1.9010    2.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239    1.7313    4.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2472    3.2405    3.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6859    2.7465    4.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4190    0.7965    2.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0837    2.7700    0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6528   -0.1897    2.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4043    0.1445    2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0222   -2.1244    1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1069   -1.8399   -0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7849   -0.6602    0.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3080   -0.1810   -1.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7209    1.6059    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1683    2.1399   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5701    1.5252   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1634   -0.1063   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6107    0.4276   -2.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8640    1.6521   -0.8903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4366   -0.4485   -4.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6905   -0.7063   -4.3417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2970    0.8943   -4.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6723   -2.3542   -0.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6911   -1.8716    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8470    1.6244   -1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6366    0.1501   -1.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7511    2.6644   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7744    0.9882   -2.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3461    2.2870   -2.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7705    2.7843   -1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
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 38 37  1  0
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M  END


  Mrv0541 02231217582D          

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M  END
> <DATABASE_ID>
HMDB0015597

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@H](CC)[C@]3([H])N(C1)CCC1=C(NC4=CC(=C(OC)C=C14)[C@@]1([H])C[C@]4([H])C(C(=O)OC)[C@@]([H])(CC5=C1NC1=CC=CC=C51)N(C)C\C4=C\C)[C@@]3(C2)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+/m0/s1

> <INCHI_KEY>
VCMIRXRRQJNZJT-XRMSBCOFSA-N

> <FORMULA>
C43H52N4O5

> <MOLECULAR_WEIGHT>
704.8968

> <EXACT_MASS>
704.393770794

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,15S,17S,18S)-17-ethyl-6-[(1R,12R,14R,15E)-15-ethylidene-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]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>
16.779474631378356

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.555075374646346

> <JCHEM_PKA_STRONGEST_BASIC>
8.525647764336558

> <JCHEM_POLAR_SURFACE_AREA>
99.89000000000001

> <JCHEM_REFRACTIVITY>
203.68439999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.23e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
voacamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015597
     RDKit          3D
Voacamine
104112  0  0  0  0  0  0  0  0999 V2000
   -3.6885    4.0783    0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3274    2.8680    1.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4771   -0.2929   -1.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6151   -1.2082    0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9982   -2.1158    1.2523 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8159    0.4503    0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4791   -1.5605    0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6478    0.9035   -0.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9451    1.6345   -0.8986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0783    1.0877   -1.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2591    2.0243   -1.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.3954    1.7119   -2.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.8033   -0.9610   -2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3190   -1.9002    1.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5643   -0.8026   -1.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2472    3.2405    3.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6528   -0.1897    2.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4043    0.1445    2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0222   -2.1244    1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1069   -1.8399   -0.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7209    1.6059    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1683    2.1399   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5701    1.5252   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1634   -0.1063   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6911   -1.8716    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8470    1.6244   -1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6366    0.1501   -1.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7511    2.6644   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7744    0.9882   -2.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3461    2.2870   -2.7245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7705    2.7843   -1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1775    3.6208   -2.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      16.899   0.729   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      14.231   1.854   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.303   0.940   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.196  -4.641   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.237  -6.555   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      15.495   5.984   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      14.515   1.093   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       6.181  -5.550   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      12.214  -2.836   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      16.455   4.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.112   3.278   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.808   2.630   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.980   5.276   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.271   2.169   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      19.165   4.194   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      18.119   5.263   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.725   2.610   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.955   5.984   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.306   6.781   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337   3.278   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.770   1.777   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.995   4.780   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.282   2.169   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.009   0.822   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      19.772   7.252   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.689   2.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.193  -0.548   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.599  -0.514   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.795  -1.828   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.029  -2.495   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.842   0.889   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.274  -1.589   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.789  -4.017   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.696  -5.262   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.556  -0.772   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      10.702  -3.073   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.217  -5.501   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.549  -2.929   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.462  -4.595   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.136  -4.415   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.829  -5.285   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       5.673  -5.078   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.909  -4.200   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.493  -7.058   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.452  -1.848   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      12.221  -6.830   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.577   2.298   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      14.456  -4.586   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.840  -0.357   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      13.758  -7.252   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      14.884  -6.123   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       3.080  -5.702   0.000  0.00  0.00           C+0
HETATM   53  H   UNK     0      16.729   5.981   0.000  0.00  0.00           H+0
HETATM   54  H   UNK     0      19.119   1.438   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0       9.278  -0.710   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0       7.220  -1.278   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0       8.421  -6.257   0.000  0.00  0.00           H+0
CONECT    1   21   35                                                       
CONECT    2   21                                                            
CONECT    3   31   47                                                       
CONECT    4   42   52                                                       
CONECT    5   42                                                            
CONECT    6   10   16   18                                                  
CONECT    7   17   24                                                       
CONECT    8   34   40   44                                                  
CONECT    9   36   43                                                       
CONECT   10    6   11   13   53                                             
CONECT   11   10   14   17   21                                             
CONECT   12   14   15   16   54                                             
CONECT   13   10   15   19                                                  
CONECT   14   11   12                                                       
CONECT   15   12   13                                                       
CONECT   16    6   12                                                       
CONECT   17    7   11   20                                                  
CONECT   18    6   22                                                       
CONECT   19   13   25                                                       
CONECT   20   17   22   23                                                  
CONECT   21    1    2   11                                                  
CONECT   22   18   20                                                       
CONECT   23   20   24   26                                                  
CONECT   24    7   23   27                                                  
CONECT   25   19                                                            
CONECT   26   23   31                                                       
CONECT   27   24   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   32   36   55                                             
CONECT   30   32   33   38   56                                             
CONECT   31    3   26   28                                                  
CONECT   32   29   30                                                       
CONECT   33   30   34   42                                                  
CONECT   34    8   33   37   57                                             
CONECT   35    1                                                            
CONECT   36    9   29   39                                                  
CONECT   37   34   39                                                       
CONECT   38   30   40   45                                                  
CONECT   39   36   37   41                                                  
CONECT   40    8   38                                                       
CONECT   41   39   43   46                                                  
CONECT   42    4    5   33                                                  
CONECT   43    9   41   48                                                  
CONECT   44    8                                                            
CONECT   45   38   49                                                       
CONECT   46   41   50                                                       
CONECT   47    3                                                            
CONECT   48   43   51                                                       
CONECT   49   45                                                            
CONECT   50   46   51                                                       
CONECT   51   48   50                                                       
CONECT   52    4                                                            
CONECT   53   10                                                            
CONECT   54   12                                                            
CONECT   55   29                                                            
CONECT   56   30                                                            
CONECT   57   34                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  130    0
END

COMPND    HMDB0015597
HETATM    1  C1  UNL     1      -3.688   4.078   0.610  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.327   2.868   1.241  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.441   1.745   0.551  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.077   0.510   1.155  1.00  0.00           C  
HETATM    5  N1  UNL     1      -5.955  -0.171   0.214  1.00  0.00           N  
HETATM    6  C5  UNL     1      -6.493  -1.425   0.734  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.477  -0.293  -1.144  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.432  -1.315  -1.438  1.00  0.00           C  
HETATM    9  C8  UNL     1      -3.529  -1.836  -0.364  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.615  -1.208   0.430  1.00  0.00           C  
HETATM   11  N2  UNL     1      -1.998  -2.116   1.252  1.00  0.00           N  
HETATM   12  C10 UNL     1      -2.482  -3.367   1.019  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.164  -4.612   1.560  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.889  -5.697   1.099  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.882  -5.570   0.141  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.200  -4.358  -0.422  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.477  -3.248   0.023  1.00  0.00           C  
HETATM   18  C16 UNL     1      -2.307   0.276   0.417  1.00  0.00           C  
HETATM   19  C17 UNL     1      -0.816   0.450   0.655  1.00  0.00           C  
HETATM   20  C18 UNL     1       0.073  -0.100  -0.251  1.00  0.00           C  
HETATM   21  C19 UNL     1       1.431   0.082   0.005  1.00  0.00           C  
HETATM   22  N3  UNL     1       2.554  -0.307  -0.652  1.00  0.00           N  
HETATM   23  C20 UNL     1       3.692   0.107   0.042  1.00  0.00           C  
HETATM   24  C21 UNL     1       3.325   0.796   1.108  1.00  0.00           C  
HETATM   25  C22 UNL     1       1.859   0.797   1.145  1.00  0.00           C  
HETATM   26  C23 UNL     1       0.952   1.351   2.052  1.00  0.00           C  
HETATM   27  C24 UNL     1      -0.395   1.157   1.775  1.00  0.00           C  
HETATM   28  O1  UNL     1      -1.326   1.672   2.622  1.00  0.00           O  
HETATM   29  C25 UNL     1      -0.842   2.390   3.759  1.00  0.00           C  
HETATM   30  C26 UNL     1       4.134   1.509   2.174  1.00  0.00           C  
HETATM   31  C27 UNL     1       5.378   2.111   1.566  1.00  0.00           C  
HETATM   32  N4  UNL     1       6.300   1.133   1.058  1.00  0.00           N  
HETATM   33  C28 UNL     1       6.526  -0.028   1.923  1.00  0.00           C  
HETATM   34  C29 UNL     1       6.757  -1.262   1.036  1.00  0.00           C  
HETATM   35  C30 UNL     1       7.893  -0.955   0.053  1.00  0.00           C  
HETATM   36  C31 UNL     1       7.454   0.193  -0.865  1.00  0.00           C  
HETATM   37  C32 UNL     1       8.523   1.289  -0.869  1.00  0.00           C  
HETATM   38  C33 UNL     1       9.809   0.745  -1.492  1.00  0.00           C  
HETATM   39  C34 UNL     1       6.131   0.760  -0.323  1.00  0.00           C  
HETATM   40  C35 UNL     1       5.043  -0.283  -0.494  1.00  0.00           C  
HETATM   41  C36 UNL     1       4.896  -0.599  -1.960  1.00  0.00           C  
HETATM   42  O2  UNL     1       5.013  -1.737  -2.348  1.00  0.00           O  
HETATM   43  O3  UNL     1       4.636   0.385  -2.836  1.00  0.00           O  
HETATM   44  C37 UNL     1       4.507   0.008  -4.232  1.00  0.00           C  
HETATM   45  C38 UNL     1       5.479  -1.560   0.248  1.00  0.00           C  
HETATM   46  C39 UNL     1      -2.648   0.903  -0.909  1.00  0.00           C  
HETATM   47  C40 UNL     1      -3.945   1.635  -0.899  1.00  0.00           C  
HETATM   48  C41 UNL     1      -5.078   1.088  -1.675  1.00  0.00           C  
HETATM   49  C42 UNL     1      -6.259   2.024  -1.617  1.00  0.00           C  
HETATM   50  O4  UNL     1      -6.182   3.056  -0.993  1.00  0.00           O  
HETATM   51  O5  UNL     1      -7.395   1.712  -2.260  1.00  0.00           O  
HETATM   52  C43 UNL     1      -8.491   2.660  -2.161  1.00  0.00           C  
HETATM   53  H1  UNL     1      -2.664   3.841   0.324  1.00  0.00           H  
HETATM   54  H2  UNL     1      -4.255   4.369  -0.275  1.00  0.00           H  
HETATM   55  H3  UNL     1      -3.684   4.901   1.325  1.00  0.00           H  
HETATM   56  H4  UNL     1      -4.693   2.918   2.256  1.00  0.00           H  
HETATM   57  H5  UNL     1      -5.678   0.824   2.024  1.00  0.00           H  
HETATM   58  H6  UNL     1      -4.316  -0.176   1.521  1.00  0.00           H  
HETATM   59  H7  UNL     1      -5.714  -2.188   0.720  1.00  0.00           H  
HETATM   60  H8  UNL     1      -6.837  -1.276   1.757  1.00  0.00           H  
HETATM   61  H9  UNL     1      -7.329  -1.748   0.113  1.00  0.00           H  
HETATM   62  H10 UNL     1      -6.364  -0.580  -1.720  1.00  0.00           H  
HETATM   63  H11 UNL     1      -4.946  -2.202  -1.862  1.00  0.00           H  
HETATM   64  H12 UNL     1      -3.803  -0.961  -2.266  1.00  0.00           H  
HETATM   65  H13 UNL     1      -1.319  -1.900   1.910  1.00  0.00           H  
HETATM   66  H14 UNL     1      -1.387  -4.724   2.301  1.00  0.00           H  
HETATM   67  H15 UNL     1      -2.673  -6.677   1.498  1.00  0.00           H  
HETATM   68  H16 UNL     1      -4.423  -6.451  -0.171  1.00  0.00           H  
HETATM   69  H17 UNL     1      -4.974  -4.269  -1.170  1.00  0.00           H  
HETATM   70  H18 UNL     1      -2.813   0.755   1.250  1.00  0.00           H  
HETATM   71  H19 UNL     1      -0.269  -0.646  -1.118  1.00  0.00           H  
HETATM   72  H20 UNL     1       2.564  -0.803  -1.486  1.00  0.00           H  
HETATM   73  H21 UNL     1       1.281   1.901   2.921  1.00  0.00           H  
HETATM   74  H22 UNL     1      -0.224   1.731   4.369  1.00  0.00           H  
HETATM   75  H23 UNL     1      -0.247   3.240   3.425  1.00  0.00           H  
HETATM   76  H24 UNL     1      -1.686   2.747   4.349  1.00  0.00           H  
HETATM   77  H25 UNL     1       4.419   0.796   2.948  1.00  0.00           H  
HETATM   78  H26 UNL     1       3.530   2.300   2.618  1.00  0.00           H  
HETATM   79  H27 UNL     1       5.885   2.707   2.325  1.00  0.00           H  
HETATM   80  H28 UNL     1       5.084   2.770   0.749  1.00  0.00           H  
HETATM   81  H29 UNL     1       5.653  -0.190   2.554  1.00  0.00           H  
HETATM   82  H30 UNL     1       7.404   0.144   2.545  1.00  0.00           H  
HETATM   83  H31 UNL     1       7.022  -2.124   1.647  1.00  0.00           H  
HETATM   84  H32 UNL     1       8.107  -1.840  -0.546  1.00  0.00           H  
HETATM   85  H33 UNL     1       8.785  -0.660   0.606  1.00  0.00           H  
HETATM   86  H34 UNL     1       7.308  -0.181  -1.878  1.00  0.00           H  
HETATM   87  H35 UNL     1       8.721   1.606   0.155  1.00  0.00           H  
HETATM   88  H36 UNL     1       8.168   2.140  -1.450  1.00  0.00           H  
HETATM   89  H37 UNL     1      10.570   1.525  -1.495  1.00  0.00           H  
HETATM   90  H38 UNL     1      10.163  -0.106  -0.911  1.00  0.00           H  
HETATM   91  H39 UNL     1       9.611   0.428  -2.516  1.00  0.00           H  
HETATM   92  H40 UNL     1       5.864   1.652  -0.890  1.00  0.00           H  
HETATM   93  H41 UNL     1       5.437  -0.449  -4.572  1.00  0.00           H  
HETATM   94  H42 UNL     1       3.691  -0.706  -4.342  1.00  0.00           H  
HETATM   95  H43 UNL     1       4.297   0.894  -4.830  1.00  0.00           H  
HETATM   96  H44 UNL     1       5.672  -2.354  -0.474  1.00  0.00           H  
HETATM   97  H45 UNL     1       4.691  -1.872   0.934  1.00  0.00           H  
HETATM   98  H46 UNL     1      -1.847   1.624  -1.168  1.00  0.00           H  
HETATM   99  H47 UNL     1      -2.637   0.150  -1.702  1.00  0.00           H  
HETATM  100  H48 UNL     1      -3.751   2.664  -1.266  1.00  0.00           H  
HETATM  101  H49 UNL     1      -4.774   0.988  -2.727  1.00  0.00           H  
HETATM  102  H50 UNL     1      -9.346   2.287  -2.724  1.00  0.00           H  
HETATM  103  H51 UNL     1      -8.771   2.784  -1.115  1.00  0.00           H  
HETATM  104  H52 UNL     1      -8.178   3.621  -2.570  1.00  0.00           H  
CONECT    1    2   53   54   55
CONECT    2    3    3   56
CONECT    3    4   47
CONECT    4    5   57   58
CONECT    5    6    7
CONECT    6   59   60   61
CONECT    7    8   48   62
CONECT    8    9   63   64
CONECT    9   10   10   17
CONECT   10   11   18
CONECT   11   12   65
CONECT   12   13   13   17
CONECT   13   14   66
CONECT   14   15   15   67
CONECT   15   16   68
CONECT   16   17   17   69
CONECT   18   19   46   70
CONECT   19   20   27   27
CONECT   20   21   21   71
CONECT   21   22   25
CONECT   22   23   72
CONECT   23   24   24   40
CONECT   24   25   30
CONECT   25   26   26
CONECT   26   27   73
CONECT   27   28
CONECT   28   29
CONECT   29   74   75   76
CONECT   30   31   77   78
CONECT   31   32   79   80
CONECT   32   33   39
CONECT   33   34   81   82
CONECT   34   35   45   83
CONECT   35   36   84   85
CONECT   36   37   39   86
CONECT   37   38   87   88
CONECT   38   89   90   91
CONECT   39   40   92
CONECT   40   41   45
CONECT   41   42   42   43
CONECT   43   44
CONECT   44   93   94   95
CONECT   45   96   97
CONECT   46   47   98   99
CONECT   47   48  100
CONECT   48   49  101
CONECT   49   50   50   51
CONECT   51   52
CONECT   52  102  103  104
END

HMDB0015597
     RDKit          3D
Voacamine
104112  0  0  0  0  0  0  0  0999 V2000
   -3.6885    4.0783    0.6104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3274    2.8680    1.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4407    1.7447    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0775    0.5101    1.1549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9547   -0.1714    0.2137 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4928   -1.4253    0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4771   -0.2929   -1.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4320   -1.3146   -1.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5294   -1.8360   -0.3642 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6151   -1.2082    0.4301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9982   -2.1158    1.2523 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4819   -3.3666    1.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1644   -4.6116    1.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8893   -5.6971    1.0989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8818   -5.5703    0.1411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2001   -4.3581   -0.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4770   -3.2475    0.0230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3074    0.2761    0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8159    0.4503    0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0732   -0.1003   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4314    0.0823    0.0053 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5545   -0.3074   -0.6525 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922    0.1068    0.0423 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3251    0.7957    1.1078 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8590    0.7975    1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9523    1.3512    2.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3947    1.1568    1.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3257    1.6719    2.6218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420    2.3901    3.7586 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1343    1.5087    2.1735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3782    2.1111    1.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2999    1.1329    1.0582 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5262   -0.0281    1.9226 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7567   -1.2615    1.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8928   -0.9546    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4544    0.1934   -0.8652 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5225    1.2888   -0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8092    0.7447   -1.4924 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1306    0.7601   -0.3234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0432   -0.2829   -0.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8962   -0.5986   -1.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0132   -1.7371   -2.3478 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6355    0.3848   -2.8358 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5069    0.0076   -4.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4791   -1.5605    0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6478    0.9035   -0.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9451    1.6345   -0.8986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0783    1.0877   -1.6748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2591    2.0243   -1.6175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1822    3.0559   -0.9931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3954    1.7119   -2.2602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4906    2.6601   -2.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6639    3.8407    0.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.3285   -1.7475    0.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3639   -0.5796   -1.7199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9456   -2.2020   -1.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8033   -0.9610   -2.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3190   -1.9002    1.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -4.7240    2.3013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6727   -6.6770    1.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4235   -6.4508   -0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9737   -4.2691   -1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8132    0.7555    1.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2694   -0.6462   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5643   -0.8026   -1.4865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2810    1.9010    2.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2239    1.7313    4.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2472    3.2405    3.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4190    0.7965    2.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5297    2.2996    2.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8846    2.7065    2.3255 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0837    2.7700    0.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6528   -0.1897    2.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4043    0.1445    2.5449 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0222   -2.1244    1.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.7209    1.6059    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1683    2.1399   -1.4503 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5701    1.5252   -1.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7744    0.9882   -2.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.7705    2.7843   -1.1153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1775    3.6208   -2.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
 38 37  1  0
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 52102  1  0
 52103  1  0
 52104  1  0
 44 93  1  0
 44 94  1  0
 44 95  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3alpha-yl)ibogamine-18-carboxylate	Kegg
Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3a-yl)ibogamine-18-carboxylate	Generator
Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3a-yl)ibogamine-18-carboxylic acid	Generator
Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3alpha-yl)ibogamine-18-carboxylic acid	Generator
Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3α-yl)ibogamine-18-carboxylate	Generator
Methyl-12-methoxy-13-(17-methoxy-17-oxovobasan-3α-yl)ibogamine-18-carboxylic acid	Generator
Voacanginine	HMDB
Vocamine	HMDB

Chemical Formula

C₄₃H₅₂N₄O₅

Average Molecular Weight

704.8968

Monoisotopic Molecular Weight

704.393770794

IUPAC Name

methyl (1S,15S,17S,18S)-17-ethyl-6-[(1R,12R,14R,15E)-15-ethylidene-18-(methoxycarbonyl)-17-methyl-10,17-diazatetracyclo[12.3.1.0³,¹¹.0⁴,⁹]octadeca-3(11),4,6,8-tetraen-12-yl]-7-methoxy-3,13-diazapentacyclo[13.3.1.0²,¹⁰.0⁴,⁹.0¹³,¹⁸]nonadeca-2(10),4,6,8-tetraene-1-carboxylate

Traditional Name

voacamine

CAS Registry Number

3371-85-5

SMILES

[H][C@@]12C[C@H](CC)[C@]3([H])N(C1)CCC1=C(NC4=CC(=C(OC)C=C14)[C@@]1([H])C[C@]4([H])C(C(=O)OC)[C@@]([H])(CC5=C1NC1=CC=CC=C51)N(C)C\C4=C\C)[C@@]3(C2)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+/m0/s1

InChI Key

VCMIRXRRQJNZJT-XRMSBCOFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ibogan-type alkaloids. These are indole alkaloids with a structure based on the ibogamine skeleton or a derivative thereof. Ibogamine is a pentacyclic heterocyclic compound consisting of an indole fused to an azepane-containing tricyclic moiety ring. Iboga alkaloids arise from the cyclization of a secodine-type precursor through the formation of a 16,21 bond.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Ibogan-type alkaloids

Sub Class

Not Available

Direct Parent

Ibogan-type alkaloids

Alternative Parents

Substituents

Ibogan skeleton
Vobasan skeleton
Catharanthine skeleton
Pyrroloazepine
3-alkylindole
Indole
Indole or derivatives
Piperidinecarboxylic acid
Anisole
Alkyl aryl ether
Azepine
Aralkylamine
Dicarboxylic acid or derivatives
Piperidine
Benzenoid
Pyrrole
Methyl ester
Heteroaromatic compound
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Ether
Amine
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015597)

Source

Exogenous

Exogenous (HMDB: HMDB0015597)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0032 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0032 g/L	ALOGPS
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
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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	301.655	30932474
DeepCCS	[M+Na]+	275.67	30932474
AllCCS	[M+H]+	258.5	32859911
AllCCS	[M+H-H2O]+	257.6	32859911
AllCCS	[M+NH4]+	259.2	32859911
AllCCS	[M+Na]+	259.4	32859911
AllCCS	[M-H]-	246.4	32859911
AllCCS	[M+Na-2H]-	250.6	32859911
AllCCS	[M+HCOO]-	255.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.62 minutes	32390414
Predicted by Siyang on May 30, 2022	14.0858 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.73 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	91.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2672.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	159.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	253.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	176.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	186.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	522.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	494.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	881.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1158.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	672.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1597.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	377.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	409.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	305.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	279.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	10.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Voacamine	[H][C@@]12C[C@H](CC)[C@]3([H])N(C1)CCC1=C(NC4=CC(=C(OC)C=C14)[C@@]1([H])C[C@]4([H])C(C(=O)OC)[C@@]([H])(CC5=C1NC1=CC=CC=C51)N(C)C\C4=C\C)[C@@]3(C2)C(=O)OC	5855.8	Standard polar	33892256
Voacamine	[H][C@@]12C[C@H](CC)[C@]3([H])N(C1)CCC1=C(NC4=CC(=C(OC)C=C14)[C@@]1([H])C[C@]4([H])C(C(=O)OC)[C@@]([H])(CC5=C1NC1=CC=CC=C51)N(C)C\C4=C\C)[C@@]3(C2)C(=O)OC	4727.3	Standard non polar	33892256
Voacamine	[H][C@@]12C[C@H](CC)[C@]3([H])N(C1)CCC1=C(NC4=CC(=C(OC)C=C14)[C@@]1([H])C[C@]4([H])C(C(=O)OC)[C@@]([H])(CC5=C1NC1=CC=CC=C51)N(C)C\C4=C\C)[C@@]3(C2)C(=O)OC	5516.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Voacamine,1TMS,isomer #1	C/C=C1/CN(C)[C@@H]2CC3=C([NH]C4=CC=CC=C34)[C@@H](C3=C(OC)C=C4C5=C(N([Si](C)(C)C)C4=C3)[C@]3(C(=O)OC)C[C@@H]4C[C@H](CC)[C@@H]3N(CC5)C4)C[C@@H]1C2C(=O)OC	5374.3	Semi standard non polar	33892256
Voacamine,1TMS,isomer #1	C/C=C1/CN(C)[C@@H]2CC3=C([NH]C4=CC=CC=C34)[C@@H](C3=C(OC)C=C4C5=C(N([Si](C)(C)C)C4=C3)[C@]3(C(=O)OC)C[C@@H]4C[C@H](CC)[C@@H]3N(CC5)C4)C[C@@H]1C2C(=O)OC	5533.7	Standard non polar	33892256
Voacamine,1TMS,isomer #1	C/C=C1/CN(C)[C@@H]2CC3=C([NH]C4=CC=CC=C34)[C@@H](C3=C(OC)C=C4C5=C(N([Si](C)(C)C)C4=C3)[C@]3(C(=O)OC)C[C@@H]4C[C@H](CC)[C@@H]3N(CC5)C4)C[C@@H]1C2C(=O)OC	7097.3	Standard polar	33892256
Voacamine,1TMS,isomer #2	C/C=C1/CN(C)[C@@H]2CC3=C([C@@H](C4=C(OC)C=C5C6=C([NH]C5=C4)[C@]4(C(=O)OC)C[C@@H]5C[C@H](CC)[C@@H]4N(CC6)C5)C[C@@H]1C2C(=O)OC)N([Si](C)(C)C)C1=CC=CC=C31	5363.1	Semi standard non polar	33892256
Voacamine,1TMS,isomer #2	C/C=C1/CN(C)[C@@H]2CC3=C([C@@H](C4=C(OC)C=C5C6=C([NH]C5=C4)[C@]4(C(=O)OC)C[C@@H]5C[C@H](CC)[C@@H]4N(CC6)C5)C[C@@H]1C2C(=O)OC)N([Si](C)(C)C)C1=CC=CC=C31	5436.4	Standard non polar	33892256
Voacamine,1TMS,isomer #2	C/C=C1/CN(C)[C@@H]2CC3=C([C@@H](C4=C(OC)C=C5C6=C([NH]C5=C4)[C@]4(C(=O)OC)C[C@@H]5C[C@H](CC)[C@@H]4N(CC6)C5)C[C@@H]1C2C(=O)OC)N([Si](C)(C)C)C1=CC=CC=C31	7097.8	Standard polar	33892256
Voacamine,2TMS,isomer #1	C/C=C1/CN(C)[C@@H]2CC3=C([C@@H](C4=C(OC)C=C5C6=C(N([Si](C)(C)C)C5=C4)[C@]4(C(=O)OC)C[C@@H]5C[C@H](CC)[C@@H]4N(CC6)C5)C[C@@H]1C2C(=O)OC)N([Si](C)(C)C)C1=CC=CC=C31	5328.6	Semi standard non polar	33892256
Voacamine,2TMS,isomer #1	C/C=C1/CN(C)[C@@H]2CC3=C([C@@H](C4=C(OC)C=C5C6=C(N([Si](C)(C)C)C5=C4)[C@]4(C(=O)OC)C[C@@H]5C[C@H](CC)[C@@H]4N(CC6)C5)C[C@@H]1C2C(=O)OC)N([Si](C)(C)C)C1=CC=CC=C31	5399.9	Standard non polar	33892256
Voacamine,2TMS,isomer #1	C/C=C1/CN(C)[C@@H]2CC3=C([C@@H](C4=C(OC)C=C5C6=C(N([Si](C)(C)C)C5=C4)[C@]4(C(=O)OC)C[C@@H]5C[C@H](CC)[C@@H]4N(CC6)C5)C[C@@H]1C2C(=O)OC)N([Si](C)(C)C)C1=CC=CC=C31	6784.5	Standard polar	33892256
Voacamine,1TBDMS,isomer #1	C/C=C1/CN(C)[C@@H]2CC3=C([NH]C4=CC=CC=C34)[C@@H](C3=C(OC)C=C4C5=C(N([Si](C)(C)C(C)(C)C)C4=C3)[C@]3(C(=O)OC)C[C@@H]4C[C@H](CC)[C@@H]3N(CC5)C4)C[C@@H]1C2C(=O)OC	5469.7	Semi standard non polar	33892256
Voacamine,1TBDMS,isomer #1	C/C=C1/CN(C)[C@@H]2CC3=C([NH]C4=CC=CC=C34)[C@@H](C3=C(OC)C=C4C5=C(N([Si](C)(C)C(C)(C)C)C4=C3)[C@]3(C(=O)OC)C[C@@H]4C[C@H](CC)[C@@H]3N(CC5)C4)C[C@@H]1C2C(=O)OC	5748.0	Standard non polar	33892256
Voacamine,1TBDMS,isomer #1	C/C=C1/CN(C)[C@@H]2CC3=C([NH]C4=CC=CC=C34)[C@@H](C3=C(OC)C=C4C5=C(N([Si](C)(C)C(C)(C)C)C4=C3)[C@]3(C(=O)OC)C[C@@H]4C[C@H](CC)[C@@H]3N(CC5)C4)C[C@@H]1C2C(=O)OC	7111.3	Standard polar	33892256
Voacamine,1TBDMS,isomer #2	C/C=C1/CN(C)[C@@H]2CC3=C([C@@H](C4=C(OC)C=C5C6=C([NH]C5=C4)[C@]4(C(=O)OC)C[C@@H]5C[C@H](CC)[C@@H]4N(CC6)C5)C[C@@H]1C2C(=O)OC)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C31	5448.3	Semi standard non polar	33892256
Voacamine,1TBDMS,isomer #2	C/C=C1/CN(C)[C@@H]2CC3=C([C@@H](C4=C(OC)C=C5C6=C([NH]C5=C4)[C@]4(C(=O)OC)C[C@@H]5C[C@H](CC)[C@@H]4N(CC6)C5)C[C@@H]1C2C(=O)OC)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C31	5646.4	Standard non polar	33892256
Voacamine,1TBDMS,isomer #2	C/C=C1/CN(C)[C@@H]2CC3=C([C@@H](C4=C(OC)C=C5C6=C([NH]C5=C4)[C@]4(C(=O)OC)C[C@@H]5C[C@H](CC)[C@@H]4N(CC6)C5)C[C@@H]1C2C(=O)OC)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C31	7113.5	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voacamine 10V, Positive-QTOF	splash10-0ab9-0000009500-a1a64a21f7d9ec3401fa	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voacamine 20V, Positive-QTOF	splash10-05g1-0001009100-2b2d3c299d1d143b7473	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voacamine 40V, Positive-QTOF	splash10-03dr-0000039000-9017d6876d59e4847db3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voacamine 10V, Negative-QTOF	splash10-0udi-0000004900-deceec71058f12cd75d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voacamine 20V, Negative-QTOF	splash10-0udr-0002009300-7d3cb4a2a467e2e222ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voacamine 40V, Negative-QTOF	splash10-052r-0013009000-b8e009201a2611beca79	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voacamine 10V, Positive-QTOF	splash10-0a4i-0000001900-a9bca08aaa1c9c199d22	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voacamine 20V, Positive-QTOF	splash10-0ab9-0000019700-071162b147ec0628021b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voacamine 40V, Positive-QTOF	splash10-00nr-0321049100-e73ebc22ad6ded604e04	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voacamine 10V, Negative-QTOF	splash10-0udi-0000003900-5c5f5379323417f95320	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voacamine 20V, Negative-QTOF	splash10-0udi-0000009700-41648dc058d6eac61119	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Voacamine 40V, Negative-QTOF	splash10-0550-0014097100-263458458d07d8a975a4	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04877	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04877	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04877

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001785

Chemspider ID

10128230

KEGG Compound ID

C09252

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Voacamine

METLIN ID

Not Available

PubChem Compound

11953931

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Meschini S, Marra M, Condello M, Calcabrini A, Federici E, Dupuis ML, Cianfriglia M, Arancia G: Voacamine, an alkaloid extracted from Peschiera fuchsiaefolia, inhibits P-glycoprotein action in multidrug-resistant tumor cells. Int J Oncol. 2005 Dec;27(6):1597-603. [PubMed:16273216 ]
Meschini S, Marra M, Calcabrini A, Federici E, Galeffi C, Arancia G: Voacamine, a bisindolic alkaloid from Peschiera fuchsiaefolia, enhances the cytotoxic effect of doxorubicin on multidrug-resistant tumor cells. Int J Oncol. 2003 Dec;23(6):1505-13. [PubMed:14612920 ]
Meschini S, Condello M, Marra M, Formisano G, Federici E, Arancia G: Autophagy-mediated chemosensitizing effect of the plant alkaloid voacamine on multidrug resistant cells. Toxicol In Vitro. 2007 Mar;21(2):197-203. Epub 2006 Sep 16. [PubMed:17070665 ]

Transporters

Enzyme Details

1. Multidrug resistance protein 1

General function:: Involved in ATP binding
Specific function:: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:: ABCB1
Uniprot ID:: P08183
Molecular weight:: 141477.3

References

Meschini S, Marra M, Condello M, Calcabrini A, Federici E, Dupuis ML, Cianfriglia M, Arancia G: Voacamine, an alkaloid extracted from Peschiera fuchsiaefolia, inhibits P-glycoprotein action in multidrug-resistant tumor cells. Int J Oncol. 2005 Dec;27(6):1597-603. [PubMed:16273216 ]
Meschini S, Marra M, Calcabrini A, Federici E, Galeffi C, Arancia G: Voacamine, a bisindolic alkaloid from Peschiera fuchsiaefolia, enhances the cytotoxic effect of doxorubicin on multidrug-resistant tumor cells. Int J Oncol. 2003 Dec;23(6):1505-13. [PubMed:14612920 ]

Showing metabocard for Voacamine (HMDB0015597)

MOL for HMDB0015597 (Voacamine)

3D MOL for HMDB0015597 (Voacamine)

3D SDF for HMDB0015597 (Voacamine)

3D-SDF for HMDB0015597 (Voacamine)

PDB for HMDB0015597 (Voacamine)

3D PDB for HMDB0015597 (Voacamine)

SMILES for HMDB0015597 (Voacamine)

INCHI for HMDB0015597 (Voacamine)

Structure for HMDB0015597 (Voacamine)

3D Structure for HMDB0015597 (Voacamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

MS/MS Spectra

Transporters

References