Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2)transporters (5) Show 7 proteins XML

enzymes (2)transporters (5) Show 7 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:35 UTC

HMDB ID

HMDB0014351

Secondary Accession Numbers

HMDB14351

Metabolite Identification

Common Name

Reserpine

Description

Reserpine, also known as apoplon or serpalan, 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. Reserpine is a very strong basic compound (based on its pKa). Reserpine is a potentially toxic compound. An alkaloid found in the roots of Rauwolfia serpentina and R. vomitoria.

Structure

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

206
  Mrv0541 02231214312D          

 47 52  0  0  1  0            999 V2000
    9.0369   -1.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1915   -0.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5976   -2.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5468   -1.1549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4832    0.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2049    1.5700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8723   -1.7140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4557    1.0837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9716   -0.4836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1074    1.7459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0836    0.8240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6474    0.1264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2224    0.7650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8083    0.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9109   -0.7290    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5553    1.1328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9505    1.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1007    0.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7849   -0.9219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3839   -0.2567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7484    1.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8524    2.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4935    2.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0455    2.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3518   -1.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734    2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4206    1.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8431   -1.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1111    2.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7411    0.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5880    1.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2743    2.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0110    1.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0385   -2.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5488    0.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0984    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8067   -0.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6143   -0.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9060    0.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1639   -0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3226   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1977    1.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5212    0.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2001   -0.3590    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6583    1.2606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1100    0.6457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  1  6  0  0  0
  1 28  1  0  0  0  0
 20  2  1  1  0  0  0
  2 30  1  0  0  0  0
  3 25  1  0  0  0  0
  3 34  1  0  0  0  0
  4 25  2  0  0  0  0
  5 30  2  0  0  0  0
  6 33  1  0  0  0  0
  6 40  1  0  0  0  0
  7 38  1  0  0  0  0
  7 42  1  0  0  0  0
  8 39  1  0  0  0  0
  8 43  1  0  0  0  0
  9 41  1  0  0  0  0
  9 44  1  0  0  0  0
 10 16  1  0  0  0  0
 10 17  1  0  0  0  0
 10 22  1  0  0  0  0
 11 21  1  0  0  0  0
 11 27  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 12 45  1  6  0  0  0
 13 17  1  0  0  0  0
 13 18  1  0  0  0  0
 13 46  1  6  0  0  0
 14 16  1  0  0  0  0
 15 19  1  0  0  0  0
 15 25  1  1  0  0  0
 16 21  1  0  0  0  0
 16 47  1  1  0  0  0
 18 20  1  0  0  0  0
 19 20  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 24  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 29  1  0  0  0  0
 27 31  1  0  0  0  0
 29 32  2  0  0  0  0
 30 35  1  0  0  0  0
 31 33  2  0  0  0  0
 32 33  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 36 39  1  0  0  0  0
 37 38  2  0  0  0  0
 38 41  1  0  0  0  0
 39 41  2  0  0  0  0
M  END

HMDB0014351
     RDKit          3D
Reserpine
 84 89  0  0  0  0  0  0  0  0999 V2000
    2.1854    4.5073    1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6226    3.7019    0.8956 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7387    2.6556    1.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4891    2.4919    2.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1732    1.8376    0.0938 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2193    1.1312   -0.7123 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1494    0.2887    0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9645   -0.5771   -0.8289 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3903   -0.6630   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1124   -1.5269    0.3249 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4061   -1.1486    0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5313   -1.6602    1.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7491   -1.0324    0.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9143   -1.5273    1.4946 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8070   -2.7094    2.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7876    0.1246    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6791    0.6541   -0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716    0.0187   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2377    0.3258   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6469    1.3906   -1.7323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6623    0.8018   -2.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8619   -0.2373   -2.1940 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366   -0.3144   -2.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5698    0.4327   -1.8633 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5969   -0.4524   -1.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    0.4576   -0.7772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8124   -0.1512   -0.4885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0338    0.3359   -0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0267    1.3819   -1.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3045   -0.3007   -0.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3822   -1.4608    0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6249   -2.0016    0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7329   -3.1626    1.1274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6393   -3.8501    1.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7897   -1.4462   -0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0521   -1.9683    0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8456   -1.6102    1.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6801   -0.2888   -0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8597    0.2966   -1.3379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7977    1.4794   -2.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4550    0.2857   -1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9070    0.9054    0.5245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7903    1.3855    1.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941    0.6394    2.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294    3.8971    2.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9335    5.1661    1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849    5.1713    2.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3067    2.5777   -0.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8511    1.9504   -1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8116    1.0009    0.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6601   -0.3290    0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678   -1.6320   -0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7452   -2.3805    0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4804   -2.5607    1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8136   -3.0832    2.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3091   -3.4661    1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2086   -2.4591    3.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7415    0.6200    0.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7243    1.5684   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314    2.2258   -1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4670    1.8559   -2.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0925    1.6283   -3.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2804    0.3695   -3.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2017   -1.3808   -2.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5737    0.1097   -3.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1015    1.2430   -2.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9843   -0.9363   -2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531   -1.2686   -0.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6814    1.3738   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4676   -1.8851    0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8060   -3.8577    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9815   -4.9081    1.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3477   -3.4515    2.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3943   -2.4936    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2580   -1.1095    2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5889   -0.8643    0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4076    2.2999   -1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1274    1.3712   -2.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8460    1.7118   -2.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4037    1.2047   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5076   -0.0711    0.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    0.4371    3.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493   -0.2868    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7396    1.2011    3.1937 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  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  2  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  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 32 35  2  0
 35 36  1  0
 36 37  1  0
 35 38  1  0
 38 39  1  0
 39 40  1  0
 38 41  2  0
 26 42  1  0
 42 43  1  0
 43 44  1  0
 42  5  1  0
 24  6  1  0
 41 30  1  0
 22  8  1  0
 19  9  2  0
 18 11  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  5 48  1  6
  6 49  1  6
  7 50  1  0
  7 51  1  0
  8 52  1  6
 10 53  1  0
 12 54  1  0
 15 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  0
 17 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  6
 25 67  1  0
 25 68  1  0
 26 69  1  6
 31 70  1  0
 34 71  1  0
 34 72  1  0
 34 73  1  0
 37 74  1  0
 37 75  1  0
 37 76  1  0
 40 77  1  0
 40 78  1  0
 40 79  1  0
 41 80  1  0
 42 81  1  1
 44 82  1  0
 44 83  1  0
 44 84  1  0
M  END

206
  Mrv0541 02231214312D          

 47 52  0  0  1  0            999 V2000
    9.0369   -1.7075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1915   -0.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5976   -2.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5468   -1.1549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4832    0.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2049    1.5700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8723   -1.7140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4557    1.0837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9716   -0.4836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1074    1.7459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0836    0.8240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6474    0.1264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2224    0.7650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8083    0.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9109   -0.7290    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5553    1.1328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9505    1.5802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1007    0.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7849   -0.9219    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3839   -0.2567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7484    1.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8524    2.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4935    2.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0455    2.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3518   -1.3357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6734    2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4206    1.3066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8431   -1.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1111    2.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7411    0.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5880    1.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2743    2.5580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0110    1.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0385   -2.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5488    0.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0984    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8067   -0.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6143   -0.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9060    0.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.1805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1639   -0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3226   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1977    1.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5212    0.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2001   -0.3590    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6583    1.2606    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1100    0.6457    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 19  1  1  6  0  0  0
  1 28  1  0  0  0  0
 20  2  1  1  0  0  0
  2 30  1  0  0  0  0
  3 25  1  0  0  0  0
  3 34  1  0  0  0  0
  4 25  2  0  0  0  0
  5 30  2  0  0  0  0
  6 33  1  0  0  0  0
  6 40  1  0  0  0  0
  7 38  1  0  0  0  0
  7 42  1  0  0  0  0
  8 39  1  0  0  0  0
  8 43  1  0  0  0  0
  9 41  1  0  0  0  0
  9 44  1  0  0  0  0
 10 16  1  0  0  0  0
 10 17  1  0  0  0  0
 10 22  1  0  0  0  0
 11 21  1  0  0  0  0
 11 27  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 12 45  1  6  0  0  0
 13 17  1  0  0  0  0
 13 18  1  0  0  0  0
 13 46  1  6  0  0  0
 14 16  1  0  0  0  0
 15 19  1  0  0  0  0
 15 25  1  1  0  0  0
 16 21  1  0  0  0  0
 16 47  1  1  0  0  0
 18 20  1  0  0  0  0
 19 20  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 24  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 29  1  0  0  0  0
 27 31  1  0  0  0  0
 29 32  2  0  0  0  0
 30 35  1  0  0  0  0
 31 33  2  0  0  0  0
 32 33  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 36 39  1  0  0  0  0
 37 38  2  0  0  0  0
 38 41  1  0  0  0  0
 39 41  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014351

> <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=C3C=CC(OC)=C1)C2

> <INCHI_IDENTIFIER>
InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1

> <INCHI_KEY>
QEVHRUUCFGRFIF-MDEJGZGSSA-N

> <FORMULA>
C33H40N2O9

> <MOLECULAR_WEIGHT>
608.6787

> <EXACT_MASS>
608.273380888

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
66.05009821117685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate

> <ALOGPS_LOGP>
4.05

> <JCHEM_LOGP>
3.531495942666668

> <ALOGPS_LOGS>
-4.73

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.29011270669428

> <JCHEM_PKA_STRONGEST_BASIC>
7.559517906091002

> <JCHEM_POLAR_SURFACE_AREA>
117.78

> <JCHEM_REFRACTIVITY>
161.41849999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
reserpine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014351
     RDKit          3D
Reserpine
 84 89  0  0  0  0  0  0  0  0999 V2000
    2.1854    4.5073    1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6226    3.7019    0.8956 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7387    2.6556    1.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4891    2.4919    2.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1732    1.8376    0.0938 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2193    1.1312   -0.7123 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1494    0.2887    0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9645   -0.5771   -0.8289 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3903   -0.6630   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1124   -1.5269    0.3249 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4061   -1.1486    0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5313   -1.6602    1.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7491   -1.0324    0.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9143   -1.5273    1.4946 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8070   -2.7094    2.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7876    0.1246    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6791    0.6541   -0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716    0.0187   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2377    0.3258   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6469    1.3906   -1.7323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6623    0.8018   -2.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8619   -0.2373   -2.1940 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366   -0.3144   -2.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5698    0.4327   -1.8633 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5969   -0.4524   -1.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    0.4576   -0.7772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8124   -0.1512   -0.4885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0338    0.3359   -0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0267    1.3819   -1.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3045   -0.3007   -0.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3822   -1.4608    0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6249   -2.0016    0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7329   -3.1626    1.1274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6393   -3.8501    1.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7897   -1.4462   -0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0521   -1.9683    0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8456   -1.6102    1.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6801   -0.2888   -0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8597    0.2966   -1.3379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7977    1.4794   -2.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4550    0.2857   -1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9070    0.9054    0.5245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7903    1.3855    1.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941    0.6394    2.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294    3.8971    2.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9335    5.1661    1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849    5.1713    2.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3067    2.5777   -0.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8511    1.9504   -1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8116    1.0009    0.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6601   -0.3290    0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678   -1.6320   -0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7452   -2.3805    0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4804   -2.5607    1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8136   -3.0832    2.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3091   -3.4661    1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2086   -2.4591    3.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7415    0.6200    0.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7243    1.5684   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314    2.2258   -1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4670    1.8559   -2.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0925    1.6283   -3.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2804    0.3695   -3.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2017   -1.3808   -2.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5737    0.1097   -3.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1015    1.2430   -2.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9843   -0.9363   -2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531   -1.2686   -0.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6814    1.3738   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4676   -1.8851    0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8060   -3.8577    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9815   -4.9081    1.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3477   -3.4515    2.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3943   -2.4936    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2580   -1.1095    2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5889   -0.8643    0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4076    2.2999   -1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1274    1.3712   -2.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8460    1.7118   -2.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4037    1.2047   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5076   -0.0711    0.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    0.4371    3.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493   -0.2868    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7396    1.2011    3.1937 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  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  2  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  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 32 35  2  0
 35 36  1  0
 36 37  1  0
 35 38  1  0
 38 39  1  0
 39 40  1  0
 38 41  2  0
 26 42  1  0
 42 43  1  0
 43 44  1  0
 42  5  1  0
 24  6  1  0
 41 30  1  0
 22  8  1  0
 19  9  2  0
 18 11  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  5 48  1  6
  6 49  1  6
  7 50  1  0
  7 51  1  0
  8 52  1  6
 10 53  1  0
 12 54  1  0
 15 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  0
 17 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  6
 25 67  1  0
 25 68  1  0
 26 69  1  6
 31 70  1  0
 34 71  1  0
 34 72  1  0
 34 73  1  0
 37 74  1  0
 37 75  1  0
 37 76  1  0
 40 77  1  0
 40 78  1  0
 40 79  1  0
 41 80  1  0
 42 81  1  1
 44 82  1  0
 44 83  1  0
 44 84  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 206                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      16.869  -3.187   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      19.024  -0.794   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      14.182  -3.963   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.221  -2.156   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      19.569   1.818   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.116   2.931   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      24.028  -3.199   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      25.117   2.023   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      26.080  -0.903   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      13.267   3.259   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       9.489   1.538   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      14.275   0.236   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.348   1.428   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.709   0.581   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.767  -1.361   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.237   2.115   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.841   2.950   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.988   1.106   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.398  -1.721   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.517  -0.479   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.730   2.435   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.791   4.724   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.255   3.899   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.285   5.044   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.723  -2.493   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.724   3.895   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.252   2.439   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.374  -3.513   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.674   5.096   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.050   0.355   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.698   2.082   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.112   4.775   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.621   3.258   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.139  -5.096   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      21.558   0.041   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      22.584   1.189   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      22.039  -1.422   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      23.547  -1.737   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      24.091   0.874   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       3.080   4.070   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      24.573  -0.588   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      23.002  -4.348   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      24.636   3.486   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      27.106   0.246   0.000  0.00  0.00           C+0
HETATM   45  H   UNK     0      13.440  -0.670   0.000  0.00  0.00           H+0
HETATM   46  H   UNK     0      16.162   2.353   0.000  0.00  0.00           H+0
HETATM   47  H   UNK     0      11.405   1.205   0.000  0.00  0.00           H+0
CONECT    1   19   28                                                       
CONECT    2   20   30                                                       
CONECT    3   25   34                                                       
CONECT    4   25                                                            
CONECT    5   30                                                            
CONECT    6   33   40                                                       
CONECT    7   38   42                                                       
CONECT    8   39   43                                                       
CONECT    9   41   44                                                       
CONECT   10   16   17   22                                                  
CONECT   11   21   27                                                       
CONECT   12   13   14   15   45                                             
CONECT   13   12   17   18   46                                             
CONECT   14   12   16                                                       
CONECT   15   12   19   25                                                  
CONECT   16   10   14   21   47                                             
CONECT   17   10   13                                                       
CONECT   18   13   20                                                       
CONECT   19    1   15   20                                                  
CONECT   20    2   18   19                                                  
CONECT   21   11   16   23                                                  
CONECT   22   10   24                                                       
CONECT   23   21   24   26                                                  
CONECT   24   22   23                                                       
CONECT   25    3    4   15                                                  
CONECT   26   23   27   29                                                  
CONECT   27   11   26   31                                                  
CONECT   28    1                                                            
CONECT   29   26   32                                                       
CONECT   30    2    5   35                                                  
CONECT   31   27   33                                                       
CONECT   32   29   33                                                       
CONECT   33    6   31   32                                                  
CONECT   34    3                                                            
CONECT   35   30   36   37                                                  
CONECT   36   35   39                                                       
CONECT   37   35   38                                                       
CONECT   38    7   37   41                                                  
CONECT   39    8   36   41                                                  
CONECT   40    6                                                            
CONECT   41    9   38   39                                                  
CONECT   42    7                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45   12                                                            
CONECT   46   13                                                            
CONECT   47   16                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  104    0
END

COMPND    HMDB0014351
HETATM    1  C1  UNL     1       2.185   4.507   1.913  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.623   3.702   0.896  1.00  0.00           O  
HETATM    3  C2  UNL     1       0.739   2.656   1.188  1.00  0.00           C  
HETATM    4  O2  UNL     1       0.489   2.492   2.410  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.173   1.838   0.094  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.219   1.131  -0.712  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.149   0.289   0.096  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.965  -0.577  -0.829  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.390  -0.663  -0.426  1.00  0.00           C  
HETATM   10  N1  UNL     1       5.112  -1.527   0.325  1.00  0.00           N  
HETATM   11  C8  UNL     1       6.406  -1.149   0.388  1.00  0.00           C  
HETATM   12  C9  UNL     1       7.531  -1.660   1.003  1.00  0.00           C  
HETATM   13  C10 UNL     1       8.749  -1.032   0.881  1.00  0.00           C  
HETATM   14  O3  UNL     1       9.914  -1.527   1.495  1.00  0.00           O  
HETATM   15  C11 UNL     1       9.807  -2.709   2.257  1.00  0.00           C  
HETATM   16  C12 UNL     1       8.788   0.125   0.120  1.00  0.00           C  
HETATM   17  C13 UNL     1       7.679   0.654  -0.503  1.00  0.00           C  
HETATM   18  C14 UNL     1       6.472   0.019  -0.374  1.00  0.00           C  
HETATM   19  C15 UNL     1       5.238   0.326  -0.879  1.00  0.00           C  
HETATM   20  C16 UNL     1       4.647   1.391  -1.732  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.662   0.802  -2.708  1.00  0.00           C  
HETATM   22  N2  UNL     1       2.862  -0.237  -2.194  1.00  0.00           N  
HETATM   23  C18 UNL     1       1.537  -0.314  -2.745  1.00  0.00           C  
HETATM   24  C19 UNL     1       0.570   0.433  -1.863  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.597  -0.452  -1.455  1.00  0.00           C  
HETATM   26  C21 UNL     1      -1.597   0.458  -0.777  1.00  0.00           C  
HETATM   27  O4  UNL     1      -2.812  -0.151  -0.488  1.00  0.00           O  
HETATM   28  C22 UNL     1      -4.034   0.336  -0.921  1.00  0.00           C  
HETATM   29  O5  UNL     1      -4.027   1.382  -1.609  1.00  0.00           O  
HETATM   30  C23 UNL     1      -5.304  -0.301  -0.620  1.00  0.00           C  
HETATM   31  C24 UNL     1      -5.382  -1.461   0.134  1.00  0.00           C  
HETATM   32  C25 UNL     1      -6.625  -2.002   0.375  1.00  0.00           C  
HETATM   33  O6  UNL     1      -6.733  -3.163   1.127  1.00  0.00           O  
HETATM   34  C26 UNL     1      -5.639  -3.850   1.679  1.00  0.00           C  
HETATM   35  C27 UNL     1      -7.790  -1.446  -0.096  1.00  0.00           C  
HETATM   36  O7  UNL     1      -9.052  -1.968   0.131  1.00  0.00           O  
HETATM   37  C28 UNL     1      -9.846  -1.610   1.245  1.00  0.00           C  
HETATM   38  C29 UNL     1      -7.680  -0.289  -0.845  1.00  0.00           C  
HETATM   39  O8  UNL     1      -8.860   0.297  -1.338  1.00  0.00           O  
HETATM   40  C30 UNL     1      -8.798   1.479  -2.109  1.00  0.00           C  
HETATM   41  C31 UNL     1      -6.455   0.286  -1.110  1.00  0.00           C  
HETATM   42  C32 UNL     1      -0.907   0.905   0.524  1.00  0.00           C  
HETATM   43  O9  UNL     1      -1.790   1.386   1.438  1.00  0.00           O  
HETATM   44  C33 UNL     1      -1.994   0.639   2.556  1.00  0.00           C  
HETATM   45  H1  UNL     1       2.629   3.897   2.724  1.00  0.00           H  
HETATM   46  H2  UNL     1       2.934   5.166   1.423  1.00  0.00           H  
HETATM   47  H3  UNL     1       1.385   5.171   2.301  1.00  0.00           H  
HETATM   48  H4  UNL     1      -0.307   2.578  -0.616  1.00  0.00           H  
HETATM   49  H5  UNL     1       1.851   1.950  -1.168  1.00  0.00           H  
HETATM   50  H6  UNL     1       2.812   1.001   0.672  1.00  0.00           H  
HETATM   51  H7  UNL     1       1.660  -0.329   0.865  1.00  0.00           H  
HETATM   52  H8  UNL     1       2.568  -1.632  -0.723  1.00  0.00           H  
HETATM   53  H9  UNL     1       4.745  -2.381   0.804  1.00  0.00           H  
HETATM   54  H10 UNL     1       7.480  -2.561   1.591  1.00  0.00           H  
HETATM   55  H11 UNL     1      10.814  -3.083   2.542  1.00  0.00           H  
HETATM   56  H12 UNL     1       9.309  -3.466   1.603  1.00  0.00           H  
HETATM   57  H13 UNL     1       9.209  -2.459   3.152  1.00  0.00           H  
HETATM   58  H14 UNL     1       9.742   0.620   0.022  1.00  0.00           H  
HETATM   59  H15 UNL     1       7.724   1.568  -1.101  1.00  0.00           H  
HETATM   60  H16 UNL     1       4.231   2.226  -1.133  1.00  0.00           H  
HETATM   61  H17 UNL     1       5.467   1.856  -2.346  1.00  0.00           H  
HETATM   62  H18 UNL     1       3.092   1.628  -3.192  1.00  0.00           H  
HETATM   63  H19 UNL     1       4.280   0.369  -3.551  1.00  0.00           H  
HETATM   64  H20 UNL     1       1.202  -1.381  -2.800  1.00  0.00           H  
HETATM   65  H21 UNL     1       1.574   0.110  -3.769  1.00  0.00           H  
HETATM   66  H22 UNL     1       0.102   1.243  -2.498  1.00  0.00           H  
HETATM   67  H23 UNL     1      -0.984  -0.936  -2.356  1.00  0.00           H  
HETATM   68  H24 UNL     1      -0.253  -1.269  -0.764  1.00  0.00           H  
HETATM   69  H25 UNL     1      -1.681   1.374  -1.389  1.00  0.00           H  
HETATM   70  H26 UNL     1      -4.468  -1.885   0.496  1.00  0.00           H  
HETATM   71  H27 UNL     1      -4.806  -3.858   0.952  1.00  0.00           H  
HETATM   72  H28 UNL     1      -5.981  -4.908   1.839  1.00  0.00           H  
HETATM   73  H29 UNL     1      -5.348  -3.451   2.674  1.00  0.00           H  
HETATM   74  H30 UNL     1     -10.394  -2.494   1.572  1.00  0.00           H  
HETATM   75  H31 UNL     1      -9.258  -1.109   2.035  1.00  0.00           H  
HETATM   76  H32 UNL     1     -10.589  -0.864   0.866  1.00  0.00           H  
HETATM   77  H33 UNL     1      -8.408   2.300  -1.467  1.00  0.00           H  
HETATM   78  H34 UNL     1      -8.127   1.371  -2.991  1.00  0.00           H  
HETATM   79  H35 UNL     1      -9.846   1.712  -2.407  1.00  0.00           H  
HETATM   80  H36 UNL     1      -6.404   1.205  -1.708  1.00  0.00           H  
HETATM   81  H37 UNL     1      -0.508  -0.071   0.934  1.00  0.00           H  
HETATM   82  H38 UNL     1      -1.143   0.437   3.199  1.00  0.00           H  
HETATM   83  H39 UNL     1      -2.549  -0.287   2.254  1.00  0.00           H  
HETATM   84  H40 UNL     1      -2.740   1.201   3.194  1.00  0.00           H  
CONECT    1    2   45   46   47
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   42   48
CONECT    6    7   24   49
CONECT    7    8   50   51
CONECT    8    9   22   52
CONECT    9   10   19   19
CONECT   10   11   53
CONECT   11   12   12   18
CONECT   12   13   54
CONECT   13   14   16   16
CONECT   14   15
CONECT   15   55   56   57
CONECT   16   17   58
CONECT   17   18   18   59
CONECT   18   19
CONECT   19   20
CONECT   20   21   60   61
CONECT   21   22   62   63
CONECT   22   23
CONECT   23   24   64   65
CONECT   24   25   66
CONECT   25   26   67   68
CONECT   26   27   42   69
CONECT   27   28
CONECT   28   29   29   30
CONECT   30   31   31   41
CONECT   31   32   70
CONECT   32   33   35   35
CONECT   33   34
CONECT   34   71   72   73
CONECT   35   36   38
CONECT   36   37
CONECT   37   74   75   76
CONECT   38   39   41   41
CONECT   39   40
CONECT   40   77   78   79
CONECT   41   80
CONECT   42   43   81
CONECT   43   44
CONECT   44   82   83   84
END

HMDB0014351
     RDKit          3D
Reserpine
 84 89  0  0  0  0  0  0  0  0999 V2000
    2.1854    4.5073    1.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6226    3.7019    0.8956 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7387    2.6556    1.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4891    2.4919    2.4100 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1732    1.8376    0.0938 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2193    1.1312   -0.7123 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1494    0.2887    0.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9645   -0.5771   -0.8289 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3903   -0.6630   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1124   -1.5269    0.3249 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4061   -1.1486    0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5313   -1.6602    1.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7491   -1.0324    0.8811 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9143   -1.5273    1.4946 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8070   -2.7094    2.2568 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7876    0.1246    0.1197 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6791    0.6541   -0.5030 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4716    0.0187   -0.3737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2377    0.3258   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6469    1.3906   -1.7323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6623    0.8018   -2.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8619   -0.2373   -2.1940 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366   -0.3144   -2.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5698    0.4327   -1.8633 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5969   -0.4524   -1.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5967    0.4576   -0.7772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8124   -0.1512   -0.4885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0338    0.3359   -0.9214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0267    1.3819   -1.6086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3045   -0.3007   -0.6199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3822   -1.4608    0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6249   -2.0016    0.3753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7329   -3.1626    1.1274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6393   -3.8501    1.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7897   -1.4462   -0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0521   -1.9683    0.1311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8456   -1.6102    1.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6801   -0.2888   -0.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8597    0.2966   -1.3379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7977    1.4794   -2.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4550    0.2857   -1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9070    0.9054    0.5245 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7903    1.3855    1.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9941    0.6394    2.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294    3.8971    2.7240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9335    5.1661    1.4229 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849    5.1713    2.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3067    2.5777   -0.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8511    1.9504   -1.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8116    1.0009    0.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6601   -0.3290    0.8655 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5678   -1.6320   -0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7452   -2.3805    0.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4804   -2.5607    1.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8136   -3.0832    2.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3091   -3.4661    1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2086   -2.4591    3.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7415    0.6200    0.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7243    1.5684   -1.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2314    2.2258   -1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4670    1.8559   -2.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0925    1.6283   -3.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2804    0.3695   -3.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2017   -1.3808   -2.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5737    0.1097   -3.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1015    1.2430   -2.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9843   -0.9363   -2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531   -1.2686   -0.7640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6814    1.3738   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4676   -1.8851    0.4961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8060   -3.8577    0.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9815   -4.9081    1.8395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3477   -3.4515    2.6742 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3943   -2.4936    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2580   -1.1095    2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5889   -0.8643    0.8664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4076    2.2999   -1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1274    1.3712   -2.9911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8460    1.7118   -2.4068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4037    1.2047   -1.7083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5076   -0.0711    0.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432    0.4371    3.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493   -0.2868    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7396    1.2011    3.1937 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  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  2  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  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 32 35  2  0
 35 36  1  0
 36 37  1  0
 35 38  1  0
 38 39  1  0
 39 40  1  0
 38 41  2  0
 26 42  1  0
 42 43  1  0
 43 44  1  0
 42  5  1  0
 24  6  1  0
 41 30  1  0
 22  8  1  0
 19  9  2  0
 18 11  1  0
  1 45  1  0
  1 46  1  0
  1 47  1  0
  5 48  1  6
  6 49  1  6
  7 50  1  0
  7 51  1  0
  8 52  1  6
 10 53  1  0
 12 54  1  0
 15 55  1  0
 15 56  1  0
 15 57  1  0
 16 58  1  0
 17 59  1  0
 20 60  1  0
 20 61  1  0
 21 62  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  6
 25 67  1  0
 25 68  1  0
 26 69  1  6
 31 70  1  0
 34 71  1  0
 34 72  1  0
 34 73  1  0
 37 74  1  0
 37 75  1  0
 37 76  1  0
 40 77  1  0
 40 78  1  0
 40 79  1  0
 41 80  1  0
 42 81  1  1
 44 82  1  0
 44 83  1  0
 44 84  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Reserpine	ChEBI
(3beta,16beta,17alpha,18beta,20alpha)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester	ChEBI
3,4,5-Trimethoxybenzoyl methyl reserpate	ChEBI
Apoplon	ChEBI
Reserpin	ChEBI
Serpalan	ChEBI
(3b,16b,17a,18b,20a)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate methyl ester	Generator
(3b,16b,17a,18b,20a)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester	Generator
(3beta,16beta,17alpha,18beta,20alpha)-11,17-Dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate methyl ester	Generator
(3Β,16β,17α,18β,20α)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylate methyl ester	Generator
(3Β,16β,17α,18β,20α)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester	Generator
3,4,5-Trimethoxybenzoyl methyl reserpic acid	Generator
Rausedil	HMDB
Serpasil	HMDB
V Serp	HMDB
V-Serp	HMDB
Raupasil	HMDB
Serpivite	HMDB
Raunervil	HMDB
Vitarine brand OF reserpine	HMDB
Rausedyl	HMDB
Vangarde brand OF reserpine	HMDB

Chemical Formula

C₃₃H₄₀N₂O₉

Average Molecular Weight

608.6787

Monoisotopic Molecular Weight

608.273380888

IUPAC Name

methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-(3,4,5-trimethoxybenzoyloxy)-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate

Traditional Name

reserpine

CAS Registry Number

50-55-5

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=C3C=CC(OC)=C1)C2

InChI Identifier

InChI=1S/C33H40N2O9/c1-38-19-7-8-20-21-9-10-35-16-18-13-27(44-32(36)17-11-25(39-2)30(41-4)26(12-17)40-3)31(42-5)28(33(37)43-6)22(18)15-24(35)29(21)34-23(20)14-19/h7-8,11-12,14,18,22,24,27-28,31,34H,9-10,13,15-16H2,1-6H3/t18-,22+,24-,27-,28+,31+/m1/s1

InChI Key

QEVHRUUCFGRFIF-MDEJGZGSSA-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

alkaloid ester (CHEBI:28487 )
yohimban alkaloid (CHEBI:28487 )
Indole alkaloids (C06539 )
Alkaloids (C06539 )

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: HMDB0014351)
Membrane (HMDB: HMDB0014351)

Source

Exogenous

Exogenous (HMDB: HMDB0014351)

Not Available

Adrenergic uptake inhibitor (HMDB: HMDB0014351)

Inhibitor

EC 3.4.21.26 (prolyl oligopeptidase) inhibitor (HMDB: HMDB0014351)

Metabolite (HMDB: HMDB0014351)

Industrial application

Antihypertensive agent (HMDB: HMDB0014351)
First generation antipsychotic (HMDB: HMDB0014351)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	264.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.011 g/L	Not Available
LogP	3.2	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	McLean	266.49	30932474
[M+H]+	McLean	252.18	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	4.05	ALOGPS
logP	3.53	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	16.29	ChemAxon
pKa (Strongest Basic)	7.56	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	117.78 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	161.42 m³·mol⁻¹	ChemAxon
Polarizability	66.05 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]-	258.895	30932474
DeepCCS	[M+Na]+	232.674	30932474
AllCCS	[M+H]+	241.7	32859911
AllCCS	[M+H-H2O]+	240.6	32859911
AllCCS	[M+NH4]+	242.8	32859911
AllCCS	[M+Na]+	243.1	32859911
AllCCS	[M-H]-	236.8	32859911
AllCCS	[M+Na-2H]-	239.6	32859911
AllCCS	[M+HCOO]-	242.9	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.	6.46 minutes	32390414
Predicted by Siyang on May 30, 2022	14.1388 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.77 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	49.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3095.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	181.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	234.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	171.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	139.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	628.3 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	579.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	475.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1144.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	591.2 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	1889.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	402.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	416.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	299.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	184.6 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	14.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Reserpine	[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=C3C=CC(OC)=C1)C2	5698.0	Standard polar	33892256
Reserpine	[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=C3C=CC(OC)=C1)C2	4492.9	Standard non polar	33892256
Reserpine	[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=C3C=CC(OC)=C1)C2	4820.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Reserpine,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=C(OC)C=C1N4[Si](C)(C)C	4595.6	Semi standard non polar	33892256
Reserpine,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=C(OC)C=C1N4[Si](C)(C)C	4482.4	Standard non polar	33892256
Reserpine,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=C(OC)C=C1N4[Si](C)(C)C	6436.0	Standard polar	33892256
Reserpine,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=C(OC)C=C1N4[Si](C)(C)C(C)(C)C	4733.0	Semi standard non polar	33892256
Reserpine,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=C(OC)C=C1N4[Si](C)(C)C(C)(C)C	4638.7	Standard non polar	33892256
Reserpine,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=C(OC)C=C1N4[Si](C)(C)C(C)(C)C	6367.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Reserpine EI-B (Non-derivatized)	splash10-052b-0944108000-d2416a07c507dd693e2b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Reserpine EI-B (Non-derivatized)	splash10-052b-0944108000-d2416a07c507dd693e2b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Reserpine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-0549060000-793104ae04e257941689	2017-09-01	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0002-2943000000-8f7998aa667566277f3f	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine Linear Ion Trap , negative-QTOF	splash10-0006-0000090000-a4f3a4e74644a66e8705	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine Linear Ion Trap , negative-QTOF	splash10-0006-0000090000-22aa398156f73127b459	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine Linear Ion Trap , negative-QTOF	splash10-0006-0000090000-1a35ce10a9657b978845	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine Linear Ion Trap , negative-QTOF	splash10-0006-0000090000-f1a507980fe5d4bc47a4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-0002-0108920000-d8cec36e08efb0c1e16e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0000009000-2bafaa3238dfda9f4989	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-0002-0916102000-d591ae99a68ca35e63b7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-006t-0911000000-1cb6207a1835b7efb13a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-00dj-0910000000-550f1f23f96cefe74849	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-05gi-1910000000-9dd2d1b6087fe8b9d1c9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-001i-1910000000-7038e3a2f74fff79f220	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0000009000-ea7c0832701dc10b3266	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-0002-0916103000-b1128c59f469bc4d949f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-006t-0911000000-8109e56a0558f3f60659	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-00dj-0910000000-c3773763c7f72b03b234	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-05gi-1910000000-21728d59759dc657e49b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-001i-1910000000-bf727df9cb8b3d8296a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-ITFT , positive-QTOF	splash10-0002-0108920000-29c40cb6bef71c53750f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Reserpine LC-ESI-QTOF , positive-QTOF	splash10-0a4i-0000009000-0004d3aa672941e611c5	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reserpine 10V, Positive-QTOF	splash10-0a4i-0004069000-dbc0a3b6edf66c8683bd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reserpine 20V, Positive-QTOF	splash10-054k-0205093000-0c6931938051f0e1a721	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reserpine 40V, Positive-QTOF	splash10-066r-6438290000-e3ef63fc93c29206b47c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reserpine 10V, Negative-QTOF	splash10-0a4i-0120029000-1e1e860a71102dcc5e5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reserpine 20V, Negative-QTOF	splash10-092c-0321092000-7fe3c97e8909b5c37599	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Reserpine 40V, Negative-QTOF	splash10-01t9-2940040000-c9fe57795b1118e171f4	2016-08-03	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 DB00206	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00206	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00206

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001763

Chemspider ID

5566

KEGG Compound ID

C06539

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Reserpine

METLIN ID

Not Available

PubChem Compound

5770

PDB ID

Not Available

ChEBI ID

28487

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)

Download (PDF)

General References

Authors unspecified: Five-year findings of the hypertension detection and follow-up program. I. Reduction in mortality of persons with high blood pressure, including mild hypertension. Hypertension Detection and Follow-up Program Cooperative Group. JAMA. 1979 Dec 7;242(23):2562-71. [PubMed:490882 ]
Authors unspecified: Prevention of stroke by antihypertensive drug treatment in older persons with isolated systolic hypertension. Final results of the Systolic Hypertension in the Elderly Program (SHEP). SHEP Cooperative Research Group. JAMA. 1991 Jun 26;265(24):3255-64. [PubMed:2046107 ]
Moser M: "Cost containment" in the management of hypertension. Ann Intern Med. 1987 Jul;107(1):107-9. [PubMed:3592424 ]
Authors unspecified: Effects of treatment on morbidity in hypertension. Results in patients with diastolic blood pressures averaging 115 through 129 mm Hg. JAMA. 1967 Dec 11;202(11):1028-34. [PubMed:4862069 ]
Chobanian AV, Bakris GL, Black HR, Cushman WC, Green LA, Izzo JL Jr, Jones DW, Materson BJ, Oparil S, Wright JT Jr, Roccella EJ: The Seventh Report of the Joint National Committee on Prevention, Detection, Evaluation, and Treatment of High Blood Pressure: the JNC 7 report. JAMA. 2003 May 21;289(19):2560-72. Epub 2003 May 14. [PubMed:12748199 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A5

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP3A5
Uniprot ID:: P20815
Molecular weight:: 57108.065

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. 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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

Enzyme Details

1. Canalicular multispecific organic anion transporter 1

General function:: Involved in ATP binding
Specific function:: Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter
Gene Name:: ABCC2
Uniprot ID:: Q92887
Molecular weight:: 174205.6

References

Tang F, Horie K, Borchardt RT: Are MDCK cells transfected with the human MRP2 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):773-9. [PubMed:12134946 ]

Enzyme Details

2. Bile salt export pump

General function:: Involved in ATP binding
Specific function:: Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:: ABCB11
Uniprot ID:: O95342
Molecular weight:: 146405.8

References

Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [PubMed:12739759 ]
Lecureur V, Sun D, Hargrove P, Schuetz EG, Kim RB, Lan LB, Schuetz JD: Cloning and expression of murine sister of P-glycoprotein reveals a more discriminating transporter than MDR1/P-glycoprotein. Mol Pharmacol. 2000 Jan;57(1):24-35. [PubMed:10617675 ]

Enzyme Details

3. 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

Geick A, Eichelbaum M, Burk O: Nuclear receptor response elements mediate induction of intestinal MDR1 by rifampin. J Biol Chem. 2001 May 4;276(18):14581-7. Epub 2001 Jan 31. [PubMed:11297522 ]
Schuetz EG, Beck WT, Schuetz JD: Modulators and substrates of P-glycoprotein and cytochrome P4503A coordinately up-regulate these proteins in human colon carcinoma cells. Mol Pharmacol. 1996 Feb;49(2):311-8. [PubMed:8632764 ]
Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514 ]
Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [PubMed:11961113 ]
Tang F, Horie K, Borchardt RT: Are MDCK cells transfected with the human MDR1 gene a good model of the human intestinal mucosa? Pharm Res. 2002 Jun;19(6):765-72. [PubMed:12134945 ]
Horie K, Tang F, Borchardt RT: Isolation and characterization of Caco-2 subclones expressing high levels of multidrug resistance protein efflux transporter. Pharm Res. 2003 Feb;20(2):161-8. [PubMed:12636153 ]
Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [PubMed:14985103 ]
Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [PubMed:12235267 ]
Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]

Enzyme Details

4. Solute carrier family 22 member 1

General function:: Involved in ion transmembrane transporter activity
Specific function:: Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:: SLC22A1
Uniprot ID:: O15245
Molecular weight:: 61187.4

References

Grundemann D, Gorboulev V, Gambaryan S, Veyhl M, Koepsell H: Drug excretion mediated by a new prototype of polyspecific transporter. Nature. 1994 Dec 8;372(6506):549-52. [PubMed:7990927 ]

Enzyme Details

5. Solute carrier family 22 member 2

General function:: Involved in ion transmembrane transporter activity
Specific function:: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, cisplatin and oxaliplatin. Cisplatin may develop a nephrotoxic action. Transport of creatinine is inhibited by fluoroquinolones such as DX-619 and LVFX. This transporter is a major determinant of the anticancer activity of oxaliplatin and may contribute to antitumor specificity
Gene Name:: SLC22A2
Uniprot ID:: O15244
Molecular weight:: 62564.0

References

Grundemann D, Koster S, Kiefer N, Breidert T, Engelhardt M, Spitzenberger F, Obermuller N, Schomig E: Transport of monoamine transmitters by the organic cation transporter type 2, OCT2. J Biol Chem. 1998 Nov 20;273(47):30915-20. [PubMed:9812985 ]

Showing metabocard for Reserpine (HMDB0014351)

MOL for HMDB0014351 (Reserpine)

3D MOL for HMDB0014351 (Reserpine)

3D SDF for HMDB0014351 (Reserpine)

3D-SDF for HMDB0014351 (Reserpine)

PDB for HMDB0014351 (Reserpine)

3D PDB for HMDB0014351 (Reserpine)

SMILES for HMDB0014351 (Reserpine)

INCHI for HMDB0014351 (Reserpine)

Structure for HMDB0014351 (Reserpine)

3D Structure for HMDB0014351 (Reserpine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

Transporters

References

References

References

References

References