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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:54 UTC

HMDB ID

HMDB0015221

Secondary Accession Numbers

HMDB15221

Metabolite Identification

Common Name

Deserpidine

Description

Deserpidine is only found in individuals that have used or taken this drug. It is an ester alkaloid drug isolated from Rauwolfia canescens (family Apocynaceae) with antipsychotic and antihypertensive properties that has been used for the control of high blood pressure and for the relief of psychotic behavior.Deserpidine's mechanism of action is through inhibition of the ATP/Mg²⁺ pump responsible for the sequestering of neurotransmitters into storage vesicles located in the presynaptic neuron. The neurotransmitters that are not sequestered in the storage vesicle are readily metabolized by monoamine oxidase (MAO) causing a reduction in catecholamines.

Structure

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

1089
  Mrv0541 02231215142D          

 45 50  0  0  1  0            999 V2000
    7.6757   -1.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8303   -0.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2364   -2.1232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1858   -1.1549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1220    0.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5111   -1.7140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0944    1.0837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6103   -0.4836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7462    1.7459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226    0.8240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2863    0.1264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8613    0.7650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4471    0.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5497   -0.7290    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1942    1.1328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5894    1.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7395    0.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4237   -0.9219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0227   -0.2567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3873    1.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4913    2.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843    2.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324    2.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9906   -1.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3123    2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0595    1.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4819   -1.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500    2.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3799    0.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2269    1.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132    2.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6774   -2.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499    1.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1876    0.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7372    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4455   -0.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2531   -0.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5448    0.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8028   -0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9614   -2.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8365    1.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1600    0.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8390   -0.3589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2972    1.2606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7489    0.6457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  6  0  0  0
  1 27  1  0  0  0  0
 19  2  1  1  0  0  0
  2 29  1  0  0  0  0
  3 24  1  0  0  0  0
  3 32  1  0  0  0  0
  4 24  2  0  0  0  0
  5 29  2  0  0  0  0
  6 37  1  0  0  0  0
  6 40  1  0  0  0  0
  7 38  1  0  0  0  0
  7 41  1  0  0  0  0
  8 39  1  0  0  0  0
  8 42  1  0  0  0  0
  9 15  1  0  0  0  0
  9 16  1  0  0  0  0
  9 21  1  0  0  0  0
 10 20  1  0  0  0  0
 10 26  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 11 43  1  6  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 12 44  1  6  0  0  0
 13 15  1  0  0  0  0
 14 18  1  0  0  0  0
 14 24  1  1  0  0  0
 15 20  1  0  0  0  0
 15 45  1  1  0  0  0
 17 19  1  0  0  0  0
 18 19  1  0  0  0  0
 20 23  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 28  2  0  0  0  0
 26 30  2  0  0  0  0
 28 31  1  0  0  0  0
 29 34  1  0  0  0  0
 30 33  1  0  0  0  0
 31 33  2  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 35 38  1  0  0  0  0
 36 37  2  0  0  0  0
 37 39  1  0  0  0  0
 38 39  2  0  0  0  0
M  END

HMDB0015221
     RDKit          3D
Deserpidine
 80 85  0  0  0  0  0  0  0  0999 V2000
   -3.2829    0.4318    4.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536   -0.2267    3.3067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5377    0.3175    2.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1646    1.4305    3.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886   -0.3808    1.5303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7960   -0.6421    0.3511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3792    0.6098   -0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658    0.2790   -1.2892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7863    0.5314   -0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804    1.0585    0.2058 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7144    0.9963   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7568    1.4033    0.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0402    1.2195    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2909    0.6311   -0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2413    0.2181   -1.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9699    0.4175   -1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7473    0.1188   -1.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2249   -0.4959   -3.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1549   -1.5110   -2.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2531   -1.0931   -1.6720 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8746   -1.3930   -1.9622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0898   -1.4940   -0.6475 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3150   -1.0983   -0.9508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1297   -0.8057    0.2774 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4166   -0.4028   -0.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4919   -1.1438    0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2528   -2.1280    1.2027 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8662   -0.8069    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8901   -1.5465    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1910   -1.2083    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2187   -1.9678    0.9298 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9523   -3.0667    1.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4207   -0.1237   -0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7222    0.2111   -0.7193 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3903    1.1191    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3850    0.6363   -0.9663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6778    1.7314   -1.7964 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917    2.4671   -2.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0915    0.2895   -0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3654    0.2957    1.0347 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1425    0.8530    2.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760    2.1817    1.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1491   -0.1982    5.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3909    0.4424    4.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815    1.4182    4.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5657   -1.4040    1.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6561   -1.2445    0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9042    1.1505    0.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6311    1.2991   -0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2101    0.9026   -2.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8709    1.4457    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5501    1.8643    1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8507    1.5457    0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3170    0.4953   -1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3643   -0.2420   -2.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0040   -0.9959   -3.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7063    0.3259   -3.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -1.7325   -3.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6761   -2.4486   -2.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4374   -0.5318   -2.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7626   -2.3431   -2.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1276   -2.5477   -0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8082   -1.9587   -1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3906   -0.2245   -1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0909   -1.6906    0.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6244   -2.3811    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4586   -2.6791    2.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3067   -3.8299    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9194   -3.5357    2.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5497    0.6474    1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3596    1.3964   -0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7555    2.0287    0.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0482    3.0194   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9110    3.1652   -3.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8308    1.7927   -2.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2426    0.8576   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1820    1.0806    0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    2.5454    2.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6109    2.8161    1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912    2.1663    0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  2  0
 33 34  1  0
 34 35  1  0
 33 36  1  0
 36 37  1  0
 37 38  1  0
 36 39  2  0
 24 40  1  0
 40 41  1  0
 41 42  1  0
 40  5  1  0
 22  6  1  0
 39 28  1  0
 20  8  1  0
 17  9  2  0
 16 11  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  5 46  1  1
  6 47  1  1
  7 48  1  0
  7 49  1  0
  8 50  1  6
 10 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 18 56  1  0
 18 57  1  0
 19 58  1  0
 19 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  1
 23 63  1  0
 23 64  1  0
 24 65  1  1
 29 66  1  0
 32 67  1  0
 32 68  1  0
 32 69  1  0
 35 70  1  0
 35 71  1  0
 35 72  1  0
 38 73  1  0
 38 74  1  0
 38 75  1  0
 39 76  1  0
 40 77  1  6
 42 78  1  0
 42 79  1  0
 42 80  1  0
M  END

1089
  Mrv0541 02231215142D          

 45 50  0  0  1  0            999 V2000
    7.6757   -1.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8303   -0.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2364   -2.1232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1858   -1.1549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1220    0.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5111   -1.7140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0944    1.0837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6103   -0.4836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7462    1.7459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7226    0.8240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2863    0.1264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8613    0.7650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4471    0.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5497   -0.7290    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1942    1.1328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.5894    1.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7395    0.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4237   -0.9219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0227   -0.2567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3873    1.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4913    2.5304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6843    2.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1324    2.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9906   -1.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3123    2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0595    1.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4819   -1.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500    2.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3799    0.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2269    1.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9132    2.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6774   -2.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499    1.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1876    0.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7372    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4455   -0.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2531   -0.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5448    0.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8028   -0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9614   -2.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8365    1.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1600    0.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8390   -0.3589    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2972    1.2606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7489    0.6457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  6  0  0  0
  1 27  1  0  0  0  0
 19  2  1  1  0  0  0
  2 29  1  0  0  0  0
  3 24  1  0  0  0  0
  3 32  1  0  0  0  0
  4 24  2  0  0  0  0
  5 29  2  0  0  0  0
  6 37  1  0  0  0  0
  6 40  1  0  0  0  0
  7 38  1  0  0  0  0
  7 41  1  0  0  0  0
  8 39  1  0  0  0  0
  8 42  1  0  0  0  0
  9 15  1  0  0  0  0
  9 16  1  0  0  0  0
  9 21  1  0  0  0  0
 10 20  1  0  0  0  0
 10 26  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 11 43  1  6  0  0  0
 12 16  1  0  0  0  0
 12 17  1  0  0  0  0
 12 44  1  6  0  0  0
 13 15  1  0  0  0  0
 14 18  1  0  0  0  0
 14 24  1  1  0  0  0
 15 20  1  0  0  0  0
 15 45  1  1  0  0  0
 17 19  1  0  0  0  0
 18 19  1  0  0  0  0
 20 23  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 28  2  0  0  0  0
 26 30  2  0  0  0  0
 28 31  1  0  0  0  0
 29 34  1  0  0  0  0
 30 33  1  0  0  0  0
 31 33  2  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 35 38  1  0  0  0  0
 36 37  2  0  0  0  0
 37 39  1  0  0  0  0
 38 39  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015221

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12C[C@@H](OC(=O)C3=CC(OC)=C(OC)C(OC)=C3)[C@H](OC)[C@@H](C(=O)OC)[C@@]1([H])C[C@@]1([H])N(CCC3=C1NC1=CC=CC=C31)C2

> <INCHI_IDENTIFIER>
InChI=1S/C32H38N2O8/c1-37-24-12-17(13-25(38-2)29(24)39-3)31(35)42-26-14-18-16-34-11-10-20-19-8-6-7-9-22(19)33-28(20)23(34)15-21(18)27(30(26)40-4)32(36)41-5/h6-9,12-13,18,21,23,26-27,30,33H,10-11,14-16H2,1-5H3/t18-,21+,23-,26-,27+,30+/m1/s1

> <INCHI_KEY>
CVBMAZKKCSYWQR-WCGOZPBSSA-N

> <FORMULA>
C32H38N2O8

> <MOLECULAR_WEIGHT>
578.6527

> <EXACT_MASS>
578.262816202

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
62.5914431939015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

> <ALOGPS_LOGP>
4.25

> <JCHEM_LOGP>
3.689167208333335

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.3749510832009

> <JCHEM_PKA_STRONGEST_BASIC>
7.571377467016942

> <JCHEM_POLAR_SURFACE_AREA>
108.55000000000001

> <JCHEM_REFRACTIVITY>
154.95529999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
deserpidine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015221
     RDKit          3D
Deserpidine
 80 85  0  0  0  0  0  0  0  0999 V2000
   -3.2829    0.4318    4.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536   -0.2267    3.3067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5377    0.3175    2.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1646    1.4305    3.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886   -0.3808    1.5303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7960   -0.6421    0.3511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3792    0.6098   -0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658    0.2790   -1.2892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7863    0.5314   -0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804    1.0585    0.2058 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7144    0.9963   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7568    1.4033    0.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0402    1.2195    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2909    0.6311   -0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2413    0.2181   -1.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9699    0.4175   -1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7473    0.1188   -1.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2249   -0.4959   -3.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1549   -1.5110   -2.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2531   -1.0931   -1.6720 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8746   -1.3930   -1.9622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0898   -1.4940   -0.6475 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3150   -1.0983   -0.9508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1297   -0.8057    0.2774 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4166   -0.4028   -0.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4919   -1.1438    0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2528   -2.1280    1.2027 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8662   -0.8069    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8901   -1.5465    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1910   -1.2083    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2187   -1.9678    0.9298 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9523   -3.0667    1.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4207   -0.1237   -0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7222    0.2111   -0.7193 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3903    1.1191    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3850    0.6363   -0.9663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6778    1.7314   -1.7964 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917    2.4671   -2.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0915    0.2895   -0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3654    0.2957    1.0347 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1425    0.8530    2.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760    2.1817    1.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1491   -0.1982    5.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3909    0.4424    4.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815    1.4182    4.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5657   -1.4040    1.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6561   -1.2445    0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9042    1.1505    0.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6311    1.2991   -0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2101    0.9026   -2.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8709    1.4457    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5501    1.8643    1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8507    1.5457    0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3170    0.4953   -1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3643   -0.2420   -2.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0040   -0.9959   -3.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7063    0.3259   -3.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -1.7325   -3.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6761   -2.4486   -2.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4374   -0.5318   -2.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7626   -2.3431   -2.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1276   -2.5477   -0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8082   -1.9587   -1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3906   -0.2245   -1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0909   -1.6906    0.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6244   -2.3811    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4586   -2.6791    2.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3067   -3.8299    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9194   -3.5357    2.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5497    0.6474    1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3596    1.3964   -0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7555    2.0287    0.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0482    3.0194   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9110    3.1652   -3.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8308    1.7927   -2.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2426    0.8576   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1820    1.0806    0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    2.5454    2.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6109    2.8161    1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912    2.1663    0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  2  0
 33 34  1  0
 34 35  1  0
 33 36  1  0
 36 37  1  0
 37 38  1  0
 36 39  2  0
 24 40  1  0
 40 41  1  0
 41 42  1  0
 40  5  1  0
 22  6  1  0
 39 28  1  0
 20  8  1  0
 17  9  2  0
 16 11  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  5 46  1  1
  6 47  1  1
  7 48  1  0
  7 49  1  0
  8 50  1  6
 10 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 18 56  1  0
 18 57  1  0
 19 58  1  0
 19 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  1
 23 63  1  0
 23 64  1  0
 24 65  1  1
 29 66  1  0
 32 67  1  0
 32 68  1  0
 32 69  1  0
 35 70  1  0
 35 71  1  0
 35 72  1  0
 38 73  1  0
 38 74  1  0
 38 75  1  0
 39 76  1  0
 40 77  1  6
 42 78  1  0
 42 79  1  0
 42 80  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1089                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      14.328  -3.187   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      16.483  -0.794   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.641  -3.963   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.680  -2.156   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      17.028   1.818   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      21.487  -3.199   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      22.576   2.023   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      23.539  -0.903   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      10.726   3.259   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0       6.949   1.538   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      11.734   0.236   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.808   1.428   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.168   0.581   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.226  -1.361   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.696   2.115   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.300   2.950   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.447   1.106   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.858  -1.721   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.976  -0.479   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.190   2.435   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.250   4.723   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.744   5.044   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.714   3.899   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.182  -2.493   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.183   3.895   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.711   2.439   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.833  -3.513   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.133   5.096   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.509   0.355   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.157   2.082   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.571   4.775   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.598  -5.096   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.080   3.258   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.017   0.041   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.043   1.189   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      19.498  -1.422   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      21.006  -1.737   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      21.550   0.874   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      22.032  -0.588   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      20.461  -4.348   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      22.095   3.485   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      24.565   0.246   0.000  0.00  0.00           C+0
HETATM   43  H   UNK     0      10.899  -0.670   0.000  0.00  0.00           H+0
HETATM   44  H   UNK     0      13.621   2.353   0.000  0.00  0.00           H+0
HETATM   45  H   UNK     0       8.865   1.205   0.000  0.00  0.00           H+0
CONECT    1   18   27                                                       
CONECT    2   19   29                                                       
CONECT    3   24   32                                                       
CONECT    4   24                                                            
CONECT    5   29                                                            
CONECT    6   37   40                                                       
CONECT    7   38   41                                                       
CONECT    8   39   42                                                       
CONECT    9   15   16   21                                                  
CONECT   10   20   26                                                       
CONECT   11   12   13   14   43                                             
CONECT   12   11   16   17   44                                             
CONECT   13   11   15                                                       
CONECT   14   11   18   24                                                  
CONECT   15    9   13   20   45                                             
CONECT   16    9   12                                                       
CONECT   17   12   19                                                       
CONECT   18    1   14   19                                                  
CONECT   19    2   17   18                                                  
CONECT   20   10   15   23                                                  
CONECT   21    9   22                                                       
CONECT   22   21   23                                                       
CONECT   23   20   22   25                                                  
CONECT   24    3    4   14                                                  
CONECT   25   23   26   28                                                  
CONECT   26   10   25   30                                                  
CONECT   27    1                                                            
CONECT   28   25   31                                                       
CONECT   29    2    5   34                                                  
CONECT   30   26   33                                                       
CONECT   31   28   33                                                       
CONECT   32    3                                                            
CONECT   33   30   31                                                       
CONECT   34   29   35   36                                                  
CONECT   35   34   38                                                       
CONECT   36   34   37                                                       
CONECT   37    6   36   39                                                  
CONECT   38    7   35   39                                                  
CONECT   39    8   37   38                                                  
CONECT   40    6                                                            
CONECT   41    7                                                            
CONECT   42    8                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   15                                                            
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

COMPND    HMDB0015221
HETATM    1  C1  UNL     1      -3.283   0.432   4.372  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.654  -0.227   3.307  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.538   0.318   2.642  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.165   1.430   3.086  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.889  -0.381   1.530  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.796  -0.642   0.351  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.379   0.610  -0.223  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.366   0.279  -1.289  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.786   0.531  -0.855  1.00  0.00           C  
HETATM   10  N1  UNL     1      -5.380   1.059   0.206  1.00  0.00           N  
HETATM   11  C8  UNL     1      -6.714   0.996  -0.010  1.00  0.00           C  
HETATM   12  C9  UNL     1      -7.757   1.403   0.771  1.00  0.00           C  
HETATM   13  C10 UNL     1      -9.040   1.219   0.304  1.00  0.00           C  
HETATM   14  C11 UNL     1      -9.291   0.631  -0.938  1.00  0.00           C  
HETATM   15  C12 UNL     1      -8.241   0.218  -1.732  1.00  0.00           C  
HETATM   16  C13 UNL     1      -6.970   0.417  -1.234  1.00  0.00           C  
HETATM   17  C14 UNL     1      -5.747   0.119  -1.777  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.225  -0.496  -3.025  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.155  -1.511  -2.699  1.00  0.00           C  
HETATM   20  N2  UNL     1      -3.253  -1.093  -1.672  1.00  0.00           N  
HETATM   21  C17 UNL     1      -1.875  -1.393  -1.962  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.090  -1.494  -0.647  1.00  0.00           C  
HETATM   23  C19 UNL     1       0.315  -1.098  -0.951  1.00  0.00           C  
HETATM   24  C20 UNL     1       1.130  -0.806   0.277  1.00  0.00           C  
HETATM   25  O3  UNL     1       2.417  -0.403  -0.065  1.00  0.00           O  
HETATM   26  C21 UNL     1       3.492  -1.144   0.458  1.00  0.00           C  
HETATM   27  O4  UNL     1       3.253  -2.128   1.203  1.00  0.00           O  
HETATM   28  C22 UNL     1       4.866  -0.807   0.163  1.00  0.00           C  
HETATM   29  C23 UNL     1       5.890  -1.546   0.686  1.00  0.00           C  
HETATM   30  C24 UNL     1       7.191  -1.208   0.392  1.00  0.00           C  
HETATM   31  O5  UNL     1       8.219  -1.968   0.930  1.00  0.00           O  
HETATM   32  C25 UNL     1       7.952  -3.067   1.762  1.00  0.00           C  
HETATM   33  C26 UNL     1       7.421  -0.124  -0.428  1.00  0.00           C  
HETATM   34  O6  UNL     1       8.722   0.211  -0.719  1.00  0.00           O  
HETATM   35  C27 UNL     1       9.390   1.119   0.130  1.00  0.00           C  
HETATM   36  C28 UNL     1       6.385   0.636  -0.966  1.00  0.00           C  
HETATM   37  O7  UNL     1       6.678   1.731  -1.796  1.00  0.00           O  
HETATM   38  C29 UNL     1       5.592   2.467  -2.315  1.00  0.00           C  
HETATM   39  C30 UNL     1       5.091   0.290  -0.666  1.00  0.00           C  
HETATM   40  C31 UNL     1       0.365   0.296   1.035  1.00  0.00           C  
HETATM   41  O8  UNL     1       1.142   0.853   2.019  1.00  0.00           O  
HETATM   42  C32 UNL     1       1.476   2.182   1.772  1.00  0.00           C  
HETATM   43  H1  UNL     1      -3.149  -0.198   5.285  1.00  0.00           H  
HETATM   44  H2  UNL     1      -4.391   0.442   4.193  1.00  0.00           H  
HETATM   45  H3  UNL     1      -2.882   1.418   4.598  1.00  0.00           H  
HETATM   46  H4  UNL     1      -0.566  -1.404   1.888  1.00  0.00           H  
HETATM   47  H5  UNL     1      -2.656  -1.244   0.755  1.00  0.00           H  
HETATM   48  H6  UNL     1      -2.904   1.150   0.593  1.00  0.00           H  
HETATM   49  H7  UNL     1      -1.631   1.299  -0.638  1.00  0.00           H  
HETATM   50  H8  UNL     1      -3.210   0.903  -2.207  1.00  0.00           H  
HETATM   51  H9  UNL     1      -4.871   1.446   1.046  1.00  0.00           H  
HETATM   52  H10 UNL     1      -7.550   1.864   1.745  1.00  0.00           H  
HETATM   53  H11 UNL     1      -9.851   1.546   0.932  1.00  0.00           H  
HETATM   54  H12 UNL     1     -10.317   0.495  -1.288  1.00  0.00           H  
HETATM   55  H13 UNL     1      -8.364  -0.242  -2.700  1.00  0.00           H  
HETATM   56  H14 UNL     1      -6.004  -0.996  -3.613  1.00  0.00           H  
HETATM   57  H15 UNL     1      -4.706   0.326  -3.590  1.00  0.00           H  
HETATM   58  H16 UNL     1      -3.616  -1.733  -3.636  1.00  0.00           H  
HETATM   59  H17 UNL     1      -4.676  -2.449  -2.372  1.00  0.00           H  
HETATM   60  H18 UNL     1      -1.437  -0.532  -2.539  1.00  0.00           H  
HETATM   61  H19 UNL     1      -1.763  -2.343  -2.525  1.00  0.00           H  
HETATM   62  H20 UNL     1      -1.128  -2.548  -0.306  1.00  0.00           H  
HETATM   63  H21 UNL     1       0.808  -1.959  -1.467  1.00  0.00           H  
HETATM   64  H22 UNL     1       0.391  -0.224  -1.627  1.00  0.00           H  
HETATM   65  H23 UNL     1       1.091  -1.691   0.942  1.00  0.00           H  
HETATM   66  H24 UNL     1       5.624  -2.381   1.320  1.00  0.00           H  
HETATM   67  H25 UNL     1       7.459  -2.679   2.674  1.00  0.00           H  
HETATM   68  H26 UNL     1       7.307  -3.830   1.282  1.00  0.00           H  
HETATM   69  H27 UNL     1       8.919  -3.536   2.027  1.00  0.00           H  
HETATM   70  H28 UNL     1       9.550   0.647   1.105  1.00  0.00           H  
HETATM   71  H29 UNL     1      10.360   1.396  -0.322  1.00  0.00           H  
HETATM   72  H30 UNL     1       8.755   2.029   0.264  1.00  0.00           H  
HETATM   73  H31 UNL     1       5.048   3.019  -1.513  1.00  0.00           H  
HETATM   74  H32 UNL     1       5.911   3.165  -3.112  1.00  0.00           H  
HETATM   75  H33 UNL     1       4.831   1.793  -2.795  1.00  0.00           H  
HETATM   76  H34 UNL     1       4.243   0.858  -1.066  1.00  0.00           H  
HETATM   77  H35 UNL     1       0.182   1.081   0.271  1.00  0.00           H  
HETATM   78  H36 UNL     1       2.097   2.545   2.617  1.00  0.00           H  
HETATM   79  H37 UNL     1       0.611   2.816   1.534  1.00  0.00           H  
HETATM   80  H38 UNL     1       2.091   2.166   0.825  1.00  0.00           H  
CONECT    1    2   43   44   45
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   40   46
CONECT    6    7   22   47
CONECT    7    8   48   49
CONECT    8    9   20   50
CONECT    9   10   17   17
CONECT   10   11   51
CONECT   11   12   12   16
CONECT   12   13   52
CONECT   13   14   14   53
CONECT   14   15   54
CONECT   15   16   16   55
CONECT   16   17
CONECT   17   18
CONECT   18   19   56   57
CONECT   19   20   58   59
CONECT   20   21
CONECT   21   22   60   61
CONECT   22   23   62
CONECT   23   24   63   64
CONECT   24   25   40   65
CONECT   25   26
CONECT   26   27   27   28
CONECT   28   29   29   39
CONECT   29   30   66
CONECT   30   31   33   33
CONECT   31   32
CONECT   32   67   68   69
CONECT   33   34   36
CONECT   34   35
CONECT   35   70   71   72
CONECT   36   37   39   39
CONECT   37   38
CONECT   38   73   74   75
CONECT   39   76
CONECT   40   41   77
CONECT   41   42
CONECT   42   78   79   80
END

HMDB0015221
     RDKit          3D
Deserpidine
 80 85  0  0  0  0  0  0  0  0999 V2000
   -3.2829    0.4318    4.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536   -0.2267    3.3067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5377    0.3175    2.6423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1646    1.4305    3.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8886   -0.3808    1.5303 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7960   -0.6421    0.3511 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3792    0.6098   -0.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3658    0.2790   -1.2892 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7863    0.5314   -0.8548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3804    1.0585    0.2058 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7144    0.9963   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7568    1.4033    0.7708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0402    1.2195    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2909    0.6311   -0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2413    0.2181   -1.7317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9699    0.4175   -1.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7473    0.1188   -1.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2249   -0.4959   -3.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1549   -1.5110   -2.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2531   -1.0931   -1.6720 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8746   -1.3930   -1.9622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0898   -1.4940   -0.6475 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3150   -1.0983   -0.9508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1297   -0.8057    0.2774 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4166   -0.4028   -0.0646 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4919   -1.1438    0.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2528   -2.1280    1.2027 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8662   -0.8069    0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8901   -1.5465    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1910   -1.2083    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2187   -1.9678    0.9298 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9523   -3.0667    1.7619 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4207   -0.1237   -0.4283 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7222    0.2111   -0.7193 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3903    1.1191    0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3850    0.6363   -0.9663 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6778    1.7314   -1.7964 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5917    2.4671   -2.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0915    0.2895   -0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3654    0.2957    1.0347 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1425    0.8530    2.0187 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4760    2.1817    1.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1491   -0.1982    5.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3909    0.4424    4.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8815    1.4182    4.5979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5657   -1.4040    1.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6561   -1.2445    0.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9042    1.1505    0.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6311    1.2991   -0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2101    0.9026   -2.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8709    1.4457    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5501    1.8643    1.7454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8507    1.5457    0.9323 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3170    0.4953   -1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3643   -0.2420   -2.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0040   -0.9959   -3.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7063    0.3259   -3.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6159   -1.7325   -3.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6761   -2.4486   -2.3717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4374   -0.5318   -2.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7626   -2.3431   -2.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1276   -2.5477   -0.3062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8082   -1.9587   -1.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3906   -0.2245   -1.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0909   -1.6906    0.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6244   -2.3811    1.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4586   -2.6791    2.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3067   -3.8299    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9194   -3.5357    2.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5497    0.6474    1.1051 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3596    1.3964   -0.3225 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7555    2.0287    0.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0482    3.0194   -1.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9110    3.1652   -3.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8308    1.7927   -2.7955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2426    0.8576   -1.0664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1820    1.0806    0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    2.5454    2.6172 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6109    2.8161    1.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0912    2.1663    0.8251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 30 33  2  0
 33 34  1  0
 34 35  1  0
 33 36  1  0
 36 37  1  0
 37 38  1  0
 36 39  2  0
 24 40  1  0
 40 41  1  0
 41 42  1  0
 40  5  1  0
 22  6  1  0
 39 28  1  0
 20  8  1  0
 17  9  2  0
 16 11  1  0
  1 43  1  0
  1 44  1  0
  1 45  1  0
  5 46  1  1
  6 47  1  1
  7 48  1  0
  7 49  1  0
  8 50  1  6
 10 51  1  0
 12 52  1  0
 13 53  1  0
 14 54  1  0
 15 55  1  0
 18 56  1  0
 18 57  1  0
 19 58  1  0
 19 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  1
 23 63  1  0
 23 64  1  0
 24 65  1  1
 29 66  1  0
 32 67  1  0
 32 68  1  0
 32 69  1  0
 35 70  1  0
 35 71  1  0
 35 72  1  0
 38 73  1  0
 38 74  1  0
 38 75  1  0
 39 76  1  0
 40 77  1  6
 42 78  1  0
 42 79  1  0
 42 80  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3beta,16beta,17alpha,18beta,20alpha)-17-Methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester	ChEBI
11-Demethoxyreserpine	ChEBI
11-Desmethoxyreserpine	ChEBI
Canescine	ChEBI
Harmonyl	ChEBI
Raunormine	ChEBI
Recanescine	ChEBI
Halmonyl	Kegg
(3b,16b,17a,18b,20a)-17-Methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate methyl ester	Generator
(3b,16b,17a,18b,20a)-17-Methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester	Generator
(3beta,16beta,17alpha,18beta,20alpha)-17-Methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate methyl ester	Generator
(3Β,16β,17α,18β,20α)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate methyl ester	Generator
(3Β,16β,17α,18β,20α)-17-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester	Generator
Deresperine	HMDB
Desepridine	HMDB
Deserpidin	HMDB
Deserpine	HMDB
Desmethoxyreserpine	HMDB

Chemical Formula

C₃₂H₃₈N₂O₈

Average Molecular Weight

578.6527

Monoisotopic Molecular Weight

578.262816202

IUPAC Name

methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4,6,8-tetraene-19-carboxylate

Traditional Name

deserpidine

CAS Registry Number

131-01-1

SMILES

[H][C@]12C[C@@H](OC(=O)C3=CC(OC)=C(OC)C(OC)=C3)[C@H](OC)[C@@H](C(=O)OC)[C@@]1([H])C[C@@]1([H])N(CCC3=C1NC1=CC=CC=C31)C2

InChI Identifier

InChI=1S/C32H38N2O8/c1-37-24-12-17(13-25(38-2)29(24)39-3)31(35)42-26-14-18-16-34-11-10-20-19-8-6-7-9-22(19)33-28(20)23(34)15-21(18)27(30(26)40-4)32(36)41-5/h6-9,12-13,18,21,23,26-27,30,33H,10-11,14-16H2,1-5H3/t18-,21+,23-,26-,27+,30+/m1/s1

InChI Key

CVBMAZKKCSYWQR-WCGOZPBSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as yohimbine alkaloids. These are alkaloids containing the pentacyclic yohimban skeleton. The Yohimbinoid alkaloids contain a carbocyclic ring E arising through C-17 to C-18 bond formation in a corynantheine precursor.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Yohimbine alkaloids

Sub Class

Not Available

Direct Parent

Yohimbine alkaloids

Alternative Parents

Substituents

Yohimbine
Corynanthean skeleton
Yohimbine alkaloid
Pyridoindole
Beta-carboline
Gallic acid or derivatives
P-methoxybenzoic acid or derivatives
M-methoxybenzoic acid or derivatives
Benzoate ester
3-alkylindole
Indole
Indole or derivatives
Benzoic acid or derivatives
Benzoyl
Phenol ether
Anisole
Phenoxy compound
Methoxybenzene
Alkyl aryl ether
Aralkylamine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Piperidine
Pyrrole
Methyl ester
Heteroaromatic compound
Tertiary aliphatic amine
Amino acid or derivatives
Tertiary amine
Carboxylic acid ester
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Azacycle
Dialkyl ether
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Amine
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heteropentacyclic compound (CHEBI:27478 )
methyl ester (CHEBI:27478 )
benzoate ester (CHEBI:27478 )
alkaloid ester (CHEBI:27478 )
yohimban alkaloid (CHEBI:27478 )
Indole alkaloids (C06541 )

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

Cytoplasm (HMDB: HMDB0015221)
Membrane (HMDB: HMDB0015221)

Source

Exogenous

Exogenous (HMDB: HMDB0015221)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	230.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.011 g/L	Not Available
LogP	3.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	4.25	ALOGPS
logP	3.69	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	16.37	ChemAxon
pKa (Strongest Basic)	7.57	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.55 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	154.96 m³·mol⁻¹	ChemAxon
Polarizability	62.59 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	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]-	254.901	30932474
DeepCCS	[M+Na]+	228.737	30932474
AllCCS	[M+H]+	236.4	32859911
AllCCS	[M+H-H2O]+	235.1	32859911
AllCCS	[M+NH4]+	237.6	32859911
AllCCS	[M+Na]+	238.0	32859911
AllCCS	[M-H]-	231.9	32859911
AllCCS	[M+Na-2H]-	234.2	32859911
AllCCS	[M+HCOO]-	237.0	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.	6.64 minutes	32390414
Predicted by Siyang on May 30, 2022	14.1772 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.54 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	46.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3118.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	180.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	226.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	170.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	154.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	621.9 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	572.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	426.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1151.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	585.2 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	1881.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	395.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	420.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	265.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	162.9 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	11.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Deserpidine	[H][C@]12C[C@@H](OC(=O)C3=CC(OC)=C(OC)C(OC)=C3)[C@H](OC)[C@@H](C(=O)OC)[C@@]1([H])C[C@@]1([H])N(CCC3=C1NC1=CC=CC=C31)C2	5531.6	Standard polar	33892256
Deserpidine	[H][C@]12C[C@@H](OC(=O)C3=CC(OC)=C(OC)C(OC)=C3)[C@H](OC)[C@@H](C(=O)OC)[C@@]1([H])C[C@@]1([H])N(CCC3=C1NC1=CC=CC=C31)C2	4176.8	Standard non polar	33892256
Deserpidine	[H][C@]12C[C@@H](OC(=O)C3=CC(OC)=C(OC)C(OC)=C3)[C@H](OC)[C@@H](C(=O)OC)[C@@]1([H])C[C@@]1([H])N(CCC3=C1NC1=CC=CC=C31)C2	4582.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Deserpidine,1TMS,isomer #1	COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=CC=C1N4[Si](C)(C)C	4441.4	Semi standard non polar	33892256
Deserpidine,1TMS,isomer #1	COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=CC=C1N4[Si](C)(C)C	4348.7	Standard non polar	33892256
Deserpidine,1TMS,isomer #1	COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=CC=C1N4[Si](C)(C)C	6061.3	Standard polar	33892256
Deserpidine,1TBDMS,isomer #1	COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=CC=C1N4[Si](C)(C)C(C)(C)C	4579.2	Semi standard non polar	33892256
Deserpidine,1TBDMS,isomer #1	COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=CC=C1N4[Si](C)(C)C(C)(C)C	4512.7	Standard non polar	33892256
Deserpidine,1TBDMS,isomer #1	COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=CC=C1N4[Si](C)(C)C(C)(C)C	6029.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Deserpidine EI-B (Non-derivatized)	splash10-014i-7967010000-b3758c647fba3c682e47	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Deserpidine EI-B (Non-derivatized)	splash10-014i-7967010000-b3758c647fba3c682e47	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Deserpidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-014j-0849160000-31b897a373d9e518c58c	2017-09-01	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deserpidine 10V, Positive-QTOF	splash10-004i-0002090000-d380a4874665812fb77b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deserpidine 20V, Positive-QTOF	splash10-016s-0204090000-c1fc5fd8f24bc1d1a680	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deserpidine 40V, Positive-QTOF	splash10-0a4i-9648240000-1c2d515bf3c44bf02721	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deserpidine 10V, Negative-QTOF	splash10-004i-0010090000-2a2e2e1b10901bf78f48	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deserpidine 20V, Negative-QTOF	splash10-0401-0211090000-9dd997b03213bc3fd926	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deserpidine 40V, Negative-QTOF	splash10-01t9-2930110000-34d5246da664b1798766	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deserpidine 10V, Positive-QTOF	splash10-004i-0101090000-f6f633c332e0a14be0b8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deserpidine 20V, Positive-QTOF	splash10-004j-0512090000-8682dbe8aa29a53b97e2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deserpidine 40V, Positive-QTOF	splash10-052p-2809220000-943412432c84f8ba8781	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deserpidine 10V, Negative-QTOF	splash10-004i-0010090000-3aa6450ab246b9e4e0cb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deserpidine 20V, Negative-QTOF	splash10-02wa-0100190000-e4cb0c7a1c4dd472e6e8	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Deserpidine 40V, Negative-QTOF	splash10-0gw1-1210960000-3407791d5c914c80a999	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB01089	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01089	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01089

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001712

Chemspider ID

8232

KEGG Compound ID

C06541

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Deserpidine

METLIN ID

Not Available

PubChem Compound

8550

PDB ID

Not Available

ChEBI ID

27478

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

Not Available

Enzymes

Enzyme Details

1. Synaptic vesicular amine transporter

General function:: Involved in transmembrane transport
Specific function:: Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis
Gene Name:: SLC18A2
Uniprot ID:: Q05940
Molecular weight:: 55712.1

References

Sievert MK, Hajipour AR, Ruoho AE: Specific derivatization of the vesicle monoamine transporter with novel carrier-free radioiodinated reserpine and tetrabenazine photoaffinity labels. Anal Biochem. 2007 Aug 1;367(1):68-78. Epub 2007 May 3. [PubMed:17559790 ]
Naudon L, Leroux-Nicollet I, Raisman-Vozari R, Botton D, Costentin J: Time-course of modifications elicited by reserpine on the density and mRNA synthesis of the vesicular monoamine transporter, and on the density of the membrane dopamine uptake complex. Synapse. 1995 Sep;21(1):29-36. [PubMed:8525459 ]
Erickson JD, Eiden LE, Hoffman BJ: Expression cloning of a reserpine-sensitive vesicular monoamine transporter. Proc Natl Acad Sci U S A. 1992 Nov 15;89(22):10993-7. [PubMed:1438304 ]
Mandela P, Chandley M, Xu YY, Zhu MY, Ordway GA: Reserpine-induced reduction in norepinephrine transporter function requires catecholamine storage vesicles. Neurochem Int. 2010 May-Jun;56(6-7):760-7. doi: 10.1016/j.neuint.2010.02.011. Epub 2010 Feb 20. [PubMed:20176067 ]
Fulton SC, Healy MD: Comparison of the effectiveness of deserpidine, reserpine, and alpha-methyltyrosine on brain biogenic amines. Fed Proc. 1976 Dec;35(14):2558-62. [PubMed:11134 ]
Loeffler LJ, Schran HF: Antibody specificity studies for reserpine, its metabolites, and synthetic reserpine congeners: radioimmunoassay. J Pharm Sci. 1979 Nov;68(11):1433-5. [PubMed:574544 ]

Showing metabocard for Deserpidine (HMDB0015221)

MOL for HMDB0015221 (Deserpidine)

3D MOL for HMDB0015221 (Deserpidine)

3D SDF for HMDB0015221 (Deserpidine)

3D-SDF for HMDB0015221 (Deserpidine)

PDB for HMDB0015221 (Deserpidine)

3D PDB for HMDB0015221 (Deserpidine)

SMILES for HMDB0015221 (Deserpidine)

INCHI for HMDB0015221 (Deserpidine)

Structure for HMDB0015221 (Deserpidine)

3D Structure for HMDB0015221 (Deserpidine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References