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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 02:51:56 UTC

HMDB ID

HMDB0015311

Secondary Accession Numbers

HMDB15311

Metabolite Identification

Common Name

Rescinnamine

Description

Rescinnamine is only found in individuals that have used or taken this drug. It is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug. It is an alkaloid obtained from Rauwolfia serpentina and other species of Rauwolfia. [Wikipedia ]Rescinnamine Binds to and inhibits the angiotensin converting enzyme. Rescinnamine competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. Inhibition of ACE results in decreased plasma angiotensin II. As angiotensin II is a vasoconstrictor and a negative-feedback mediator for renin activity, lower concentrations result in a decrease in blood pressure and stimulation of baroreceptor reflex mechanisms, which leads to decreased vasopressor activity and to decreased aldosterone secretion.

Structure

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

1180
  Mrv0541 02231215182D          

 49 54  0  0  1  0            999 V2000
    9.0363   -1.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1908   -0.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.2286   -1.2671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 41 43  1  0  0  0  0
 42 43  2  0  0  0  0
M  END

HMDB0015311
     RDKit          3D
Rescinnamine
 88 93  0  0  0  0  0  0  0  0999 V2000
    0.3226    4.0142   -2.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1357    3.5718   -1.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

1180
  Mrv0541 02231215182D          

 49 54  0  0  1  0            999 V2000
    9.0363   -1.7074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1908   -0.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.8118    1.5303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3278   -0.0368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1069    1.7458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0832    0.8239    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6469    0.1264    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.2218    0.7649    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8078    0.3115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9102   -0.7289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5548    1.1327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9499    1.5801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1000    0.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7843   -0.9218    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3832   -0.2567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7480    1.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8519    2.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4931    2.0888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0451    2.7018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3513   -1.3356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6731    2.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4203    1.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8424   -1.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1108    2.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7403    0.1901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5877    1.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2741    2.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0108    1.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0380   -2.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5480    0.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0975    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499    2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9051    0.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4546    1.0836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1630   -0.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9706   -0.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2623    0.9151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5202    0.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6789   -1.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5539    2.3139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8774    0.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1996   -0.3590    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6577    1.2605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1096    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 37  1  0  0  0  0
  7 41  1  0  0  0  0
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  8 42  1  0  0  0  0
  8 45  1  0  0  0  0
  9 43  1  0  0  0  0
  9 46  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
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 12 14  1  0  0  0  0
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 13 18  1  0  0  0  0
 13 48  1  6  0  0  0
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 15 25  1  1  0  0  0
 16 21  1  0  0  0  0
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 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  3  0  0  0
 36 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 39 42  1  0  0  0  0
 40 41  2  0  0  0  0
 41 43  1  0  0  0  0
 42 43  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015311

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12C[C@@H](OC(=O)C=CC3=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/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/t20-,24+,26-,29-,31+,34+/m1/s1

> <INCHI_KEY>
SZLZWPPUNLXJEA-LAFLMMDJSA-N

> <FORMULA>
C35H42N2O9

> <MOLECULAR_WEIGHT>
634.716

> <EXACT_MASS>
634.289030952

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
69.65449428175995

> <JCHEM_BIOAVAILABILITY>
0

> <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-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate

> <ALOGPS_LOGP>
4.48

> <JCHEM_LOGP>
4.070086811999999

> <ALOGPS_LOGS>
-5.26

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.290112706694284

> <JCHEM_PKA_STRONGEST_BASIC>
7.559517906323249

> <JCHEM_POLAR_SURFACE_AREA>
117.78

> <JCHEM_REFRACTIVITY>
171.16419999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rescinnamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015311
     RDKit          3D
Rescinnamine
 88 93  0  0  0  0  0  0  0  0999 V2000
    0.3226    4.0142   -2.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1357    3.5718   -1.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8231    2.6275   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5082    2.1877   -1.6607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0565    2.1395    0.6461 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1484    1.1450    0.8336 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4077    1.5746    0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9679    0.7482   -0.9041 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3525    0.2445   -0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2665    0.4723    0.3590 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3657   -0.2872    0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5420   -0.4123    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5126   -1.2856    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7174   -1.4179    1.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7035   -2.3020    0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2970   -2.0345   -0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1088   -1.9124   -1.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1654   -1.0423   -0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8931   -0.6982   -1.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1314   -1.1683   -2.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6607   -1.1153   -2.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1879   -0.3716   -1.2733 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6096   -1.1177   -0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454   -0.2799    0.6677 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3079   -0.4197    0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275    0.2532    1.2506 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9097    0.0085    1.0375 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -0.6973    1.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989   -1.1631    2.9764 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125   -0.9196    1.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6687   -0.4484    0.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0659   -0.6600    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9232   -1.3517    1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2726   -1.5357    0.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1341   -2.2313    1.6243 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6045   -2.7638    2.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7366   -0.9963   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0687   -1.1559   -0.7296 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9713   -0.1552   -0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9197   -0.2965   -1.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4302    0.2286   -2.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5605    0.9387   -3.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6051   -0.1384   -0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2801    1.7130    1.1949 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4636    2.2057    2.5096 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5434    3.0460    2.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0888    5.0825   -2.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2268    3.3968   -3.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4126    3.9358   -2.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357    3.0633    1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3861    1.2227    1.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2536    1.7456    0.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2503    2.6283   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1183    1.3583   -1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1771    1.1267    1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7243    0.1650    1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1507   -1.9257   -0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2942   -3.3209    0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4796   -2.4398    1.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0606   -2.7250   -1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9107   -2.4937   -2.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4826   -0.5883   -3.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4469   -2.2293   -2.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427   -2.1568   -2.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2059   -0.6749   -3.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4082   -1.6433    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0206   -1.9597   -0.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1928   -0.2099    2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6815   -1.4708    2.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0659    0.1206   -0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5696   -1.7800    2.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.4414   -3.2368    3.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6432    0.7899   -0.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0123   -0.3615   -0.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9264   -0.0262    0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0370    1.7626   -2.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7520    0.2449   -3.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0847    1.3657   -4.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9399    0.3995   -1.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1154    2.1818    0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4744    3.9503    1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5213    2.5095    2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5515    3.4242    3.6639 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
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  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
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 44  5  1  0
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 22  8  1  0
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 18 11  1  0
  1 47  1  0
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  5 50  1  1
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 15 57  1  0
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 43 84  1  0
 44 85  1  6
 46 86  1  0
 46 87  1  0
 46 88  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1180                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      16.868  -3.187   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      19.023  -0.793   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      14.181  -3.963   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.220  -2.156   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      19.567   1.817   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       4.116   2.930   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      26.560  -2.365   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      27.649   2.857   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      28.612  -0.069   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      13.266   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      14.274   0.236   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.347   1.428   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.708   0.581   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.766  -1.361   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.236   2.114   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.840   2.949   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.987   1.106   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.397  -1.721   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.515  -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      12.790   4.723   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.254   3.899   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.284   5.043   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.722  -2.493   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.723   3.895   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.251   2.439   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.372  -3.513   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.674   5.095   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.049   0.355   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.697   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       5.620   3.258   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      13.138  -5.095   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      21.556   0.041   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      22.582   1.189   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.080   4.070   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      24.089   0.874   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      25.115   2.023   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      24.571  -0.588   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      26.078  -0.903   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      26.623   1.708   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      27.104   0.246   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      25.534  -3.514   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      27.167   4.319   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      29.638   1.080   0.000  0.00  0.00           C+0
HETATM   47  H   UNK     0      13.439  -0.670   0.000  0.00  0.00           H+0
HETATM   48  H   UNK     0      16.161   2.353   0.000  0.00  0.00           H+0
HETATM   49  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   37                                                       
CONECT    7   41   44                                                       
CONECT    8   42   45                                                       
CONECT    9   43   46                                                       
CONECT   10   16   17   22                                                  
CONECT   11   21   27                                                       
CONECT   12   13   14   15   47                                             
CONECT   13   12   17   18   48                                             
CONECT   14   12   16                                                       
CONECT   15   12   19   25                                                  
CONECT   16   10   14   21   49                                             
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                                                       
CONECT   36   35   38                                                       
CONECT   37    6                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38   42                                                       
CONECT   40   38   41                                                       
CONECT   41    7   40   43                                                  
CONECT   42    8   39   43                                                  
CONECT   43    9   41   42                                                  
CONECT   44    7                                                            
CONECT   45    8                                                            
CONECT   46    9                                                            
CONECT   47   12                                                            
CONECT   48   13                                                            
CONECT   49   16                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  108    0
END

COMPND    HMDB0015311
HETATM    1  C1  UNL     1       0.323   4.014  -2.403  1.00  0.00           C  
HETATM    2  O1  UNL     1       0.136   3.572  -1.049  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.823   2.627  -0.721  1.00  0.00           C  
HETATM    4  O2  UNL     1      -1.508   2.188  -1.661  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.057   2.139   0.646  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.148   1.145   0.834  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.408   1.575   0.175  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.968   0.748  -0.904  1.00  0.00           C  
HETATM    9  C7  UNL     1      -5.353   0.245  -0.585  1.00  0.00           C  
HETATM   10  N1  UNL     1      -6.267   0.472   0.359  1.00  0.00           N  
HETATM   11  C8  UNL     1      -7.366  -0.287   0.147  1.00  0.00           C  
HETATM   12  C9  UNL     1      -8.542  -0.412   0.817  1.00  0.00           C  
HETATM   13  C10 UNL     1      -9.513  -1.286   0.367  1.00  0.00           C  
HETATM   14  O3  UNL     1     -10.717  -1.418   1.049  1.00  0.00           O  
HETATM   15  C11 UNL     1     -11.703  -2.302   0.596  1.00  0.00           C  
HETATM   16  C12 UNL     1      -9.297  -2.035  -0.762  1.00  0.00           C  
HETATM   17  C13 UNL     1      -8.109  -1.912  -1.445  1.00  0.00           C  
HETATM   18  C14 UNL     1      -7.165  -1.042  -0.979  1.00  0.00           C  
HETATM   19  C15 UNL     1      -5.893  -0.698  -1.431  1.00  0.00           C  
HETATM   20  C16 UNL     1      -5.131  -1.168  -2.586  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.661  -1.115  -2.391  1.00  0.00           C  
HETATM   22  N2  UNL     1      -3.188  -0.372  -1.273  1.00  0.00           N  
HETATM   23  C18 UNL     1      -2.610  -1.118  -0.228  1.00  0.00           C  
HETATM   24  C19 UNL     1      -1.745  -0.280   0.668  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.308  -0.420   0.189  1.00  0.00           C  
HETATM   26  C21 UNL     1       0.528   0.253   1.251  1.00  0.00           C  
HETATM   27  O4  UNL     1       1.910   0.009   1.037  1.00  0.00           O  
HETATM   28  C22 UNL     1       2.683  -0.697   1.925  1.00  0.00           C  
HETATM   29  O5  UNL     1       2.199  -1.163   2.976  1.00  0.00           O  
HETATM   30  C23 UNL     1       4.113  -0.920   1.649  1.00  0.00           C  
HETATM   31  C24 UNL     1       4.669  -0.448   0.553  1.00  0.00           C  
HETATM   32  C25 UNL     1       6.066  -0.660   0.273  1.00  0.00           C  
HETATM   33  C26 UNL     1       6.923  -1.352   1.100  1.00  0.00           C  
HETATM   34  C27 UNL     1       8.273  -1.536   0.792  1.00  0.00           C  
HETATM   35  O6  UNL     1       9.134  -2.231   1.624  1.00  0.00           O  
HETATM   36  C28 UNL     1       8.604  -2.764   2.821  1.00  0.00           C  
HETATM   37  C29 UNL     1       8.737  -0.996  -0.386  1.00  0.00           C  
HETATM   38  O7  UNL     1      10.069  -1.156  -0.730  1.00  0.00           O  
HETATM   39  C30 UNL     1      10.971  -0.155  -0.285  1.00  0.00           C  
HETATM   40  C31 UNL     1       7.920  -0.296  -1.247  1.00  0.00           C  
HETATM   41  O8  UNL     1       8.430   0.229  -2.422  1.00  0.00           O  
HETATM   42  C32 UNL     1       7.561   0.939  -3.277  1.00  0.00           C  
HETATM   43  C33 UNL     1       6.605  -0.138  -0.909  1.00  0.00           C  
HETATM   44  C34 UNL     1       0.280   1.713   1.195  1.00  0.00           C  
HETATM   45  O9  UNL     1       0.464   2.206   2.510  1.00  0.00           O  
HETATM   46  C35 UNL     1       1.543   3.046   2.622  1.00  0.00           C  
HETATM   47  H1  UNL     1       0.089   5.083  -2.418  1.00  0.00           H  
HETATM   48  H2  UNL     1      -0.227   3.397  -3.117  1.00  0.00           H  
HETATM   49  H3  UNL     1       1.413   3.936  -2.685  1.00  0.00           H  
HETATM   50  H4  UNL     1      -1.336   3.063   1.244  1.00  0.00           H  
HETATM   51  H5  UNL     1      -2.386   1.223   1.955  1.00  0.00           H  
HETATM   52  H6  UNL     1      -4.254   1.746   0.921  1.00  0.00           H  
HETATM   53  H7  UNL     1      -3.250   2.628  -0.217  1.00  0.00           H  
HETATM   54  H8  UNL     1      -4.118   1.358  -1.847  1.00  0.00           H  
HETATM   55  H9  UNL     1      -6.177   1.127   1.149  1.00  0.00           H  
HETATM   56  H10 UNL     1      -8.724   0.165   1.699  1.00  0.00           H  
HETATM   57  H11 UNL     1     -12.151  -1.926  -0.344  1.00  0.00           H  
HETATM   58  H12 UNL     1     -11.294  -3.321   0.396  1.00  0.00           H  
HETATM   59  H13 UNL     1     -12.480  -2.440   1.392  1.00  0.00           H  
HETATM   60  H14 UNL     1     -10.061  -2.725  -1.121  1.00  0.00           H  
HETATM   61  H15 UNL     1      -7.911  -2.494  -2.343  1.00  0.00           H  
HETATM   62  H16 UNL     1      -5.483  -0.588  -3.476  1.00  0.00           H  
HETATM   63  H17 UNL     1      -5.447  -2.229  -2.812  1.00  0.00           H  
HETATM   64  H18 UNL     1      -3.243  -2.157  -2.321  1.00  0.00           H  
HETATM   65  H19 UNL     1      -3.206  -0.675  -3.324  1.00  0.00           H  
HETATM   66  H20 UNL     1      -3.408  -1.643   0.368  1.00  0.00           H  
HETATM   67  H21 UNL     1      -2.021  -1.960  -0.677  1.00  0.00           H  
HETATM   68  H22 UNL     1      -1.732  -0.854   1.648  1.00  0.00           H  
HETATM   69  H23 UNL     1      -0.036  -1.496   0.204  1.00  0.00           H  
HETATM   70  H24 UNL     1      -0.145  -0.046  -0.819  1.00  0.00           H  
HETATM   71  H25 UNL     1       0.193  -0.210   2.224  1.00  0.00           H  
HETATM   72  H26 UNL     1       4.681  -1.471   2.359  1.00  0.00           H  
HETATM   73  H27 UNL     1       4.066   0.121  -0.172  1.00  0.00           H  
HETATM   74  H28 UNL     1       6.570  -1.780   2.029  1.00  0.00           H  
HETATM   75  H29 UNL     1       8.070  -2.002   3.416  1.00  0.00           H  
HETATM   76  H30 UNL     1       7.847  -3.575   2.613  1.00  0.00           H  
HETATM   77  H31 UNL     1       9.441  -3.237   3.389  1.00  0.00           H  
HETATM   78  H32 UNL     1      10.643   0.790  -0.785  1.00  0.00           H  
HETATM   79  H33 UNL     1      12.012  -0.361  -0.639  1.00  0.00           H  
HETATM   80  H34 UNL     1      10.926  -0.026   0.812  1.00  0.00           H  
HETATM   81  H35 UNL     1       7.037   1.763  -2.760  1.00  0.00           H  
HETATM   82  H36 UNL     1       6.752   0.245  -3.630  1.00  0.00           H  
HETATM   83  H37 UNL     1       8.085   1.366  -4.143  1.00  0.00           H  
HETATM   84  H38 UNL     1       5.940   0.400  -1.553  1.00  0.00           H  
HETATM   85  H39 UNL     1       1.115   2.182   0.607  1.00  0.00           H  
HETATM   86  H40 UNL     1       1.474   3.950   1.974  1.00  0.00           H  
HETATM   87  H41 UNL     1       2.521   2.509   2.485  1.00  0.00           H  
HETATM   88  H42 UNL     1       1.552   3.424   3.664  1.00  0.00           H  
CONECT    1    2   47   48   49
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   44   50
CONECT    6    7   24   51
CONECT    7    8   52   53
CONECT    8    9   22   54
CONECT    9   10   19   19
CONECT   10   11   55
CONECT   11   12   12   18
CONECT   12   13   56
CONECT   13   14   16   16
CONECT   14   15
CONECT   15   57   58   59
CONECT   16   17   60
CONECT   17   18   18   61
CONECT   18   19
CONECT   19   20
CONECT   20   21   62   63
CONECT   21   22   64   65
CONECT   22   23
CONECT   23   24   66   67
CONECT   24   25   68
CONECT   25   26   69   70
CONECT   26   27   44   71
CONECT   27   28
CONECT   28   29   29   30
CONECT   30   31   31   72
CONECT   31   32   73
CONECT   32   33   33   43
CONECT   33   34   74
CONECT   34   35   37   37
CONECT   35   36
CONECT   36   75   76   77
CONECT   37   38   40
CONECT   38   39
CONECT   39   78   79   80
CONECT   40   41   43   43
CONECT   41   42
CONECT   42   81   82   83
CONECT   43   84
CONECT   44   45   85
CONECT   45   46
CONECT   46   86   87   88
END

HMDB0015311
     RDKit          3D
Rescinnamine
 88 93  0  0  0  0  0  0  0  0999 V2000
    0.3226    4.0142   -2.4030 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1357    3.5718   -1.0489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8231    2.6275   -0.7211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5082    2.1877   -1.6607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0565    2.1395    0.6461 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1484    1.1450    0.8336 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4077    1.5746    0.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9679    0.7482   -0.9041 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3525    0.2445   -0.5847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2665    0.4723    0.3590 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3657   -0.2872    0.1468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5420   -0.4123    0.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5126   -1.2856    0.3670 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7174   -1.4179    1.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7035   -2.3020    0.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2970   -2.0345   -0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1088   -1.9124   -1.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1654   -1.0423   -0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8931   -0.6982   -1.4313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1314   -1.1683   -2.5861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6607   -1.1153   -2.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1879   -0.3716   -1.2733 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6096   -1.1177   -0.2278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7454   -0.2799    0.6677 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3079   -0.4197    0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275    0.2532    1.2506 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9097    0.0085    1.0375 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6825   -0.6973    1.9252 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989   -1.1631    2.9764 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125   -0.9196    1.6488 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6687   -0.4484    0.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0659   -0.6600    0.2730 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9232   -1.3517    1.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2726   -1.5357    0.7922 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1341   -2.2313    1.6243 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6045   -2.7638    2.8213 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7366   -0.9963   -0.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0687   -1.1559   -0.7296 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9713   -0.1552   -0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9197   -0.2965   -1.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4302    0.2286   -2.4220 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5605    0.9387   -3.2766 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6051   -0.1384   -0.9092 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2801    1.7130    1.1949 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4636    2.2057    2.5096 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5434    3.0460    2.6218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0888    5.0825   -2.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2268    3.3968   -3.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4126    3.9358   -2.6845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3357    3.0633    1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3861    1.2227    1.9552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2536    1.7456    0.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2503    2.6283   -0.2169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1183    1.3583   -1.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1771    1.1267    1.1488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7243    0.1650    1.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1507   -1.9257   -0.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2942   -3.3209    0.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4796   -2.4398    1.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0606   -2.7250   -1.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9107   -2.4937   -2.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4826   -0.5883   -3.4760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4469   -2.2293   -2.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2427   -2.1568   -2.3207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2059   -0.6749   -3.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4082   -1.6433    0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0206   -1.9597   -0.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7317   -0.8537    1.6477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0355   -1.4957    0.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449   -0.0462   -0.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1928   -0.2099    2.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6815   -1.4708    2.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0659    0.1206   -0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5696   -1.7800    2.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0704   -2.0016    3.4160 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8473   -3.5748    2.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4414   -3.2368    3.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6432    0.7899   -0.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0123   -0.3615   -0.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9264   -0.0262    0.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0370    1.7626   -2.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7520    0.2449   -3.6303 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0847    1.3657   -4.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9399    0.3995   -1.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1154    2.1818    0.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4744    3.9503    1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5213    2.5095    2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5515    3.4242    3.6639 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  3
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 34 37  2  0
 37 38  1  0
 38 39  1  0
 37 40  1  0
 40 41  1  0
 41 42  1  0
 40 43  2  0
 26 44  1  0
 44 45  1  0
 45 46  1  0
 44  5  1  0
 24  6  1  0
 43 32  1  0
 22  8  1  0
 19  9  2  0
 18 11  1  0
  1 47  1  0
  1 48  1  0
  1 49  1  0
  5 50  1  1
  6 51  1  1
  7 52  1  0
  7 53  1  0
  8 54  1  6
 10 55  1  0
 12 56  1  0
 15 57  1  0
 15 58  1  0
 15 59  1  0
 16 60  1  0
 17 61  1  0
 20 62  1  0
 20 63  1  0
 21 64  1  0
 21 65  1  0
 23 66  1  0
 23 67  1  0
 24 68  1  1
 25 69  1  0
 25 70  1  0
 26 71  1  1
 30 72  1  0
 31 73  1  0
 33 74  1  0
 36 75  1  0
 36 76  1  0
 36 77  1  0
 39 78  1  0
 39 79  1  0
 39 80  1  0
 42 81  1  0
 42 82  1  0
 42 83  1  0
 43 84  1  0
 44 85  1  6
 46 86  1  0
 46 87  1  0
 46 88  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl trimethoxycinnamoylreserpate	HMDB
Recinnamine	HMDB
Rescinnamin	HMDB
Reserpinene	HMDB
Reserpinin	HMDB
Reserpinine	HMDB
Trimethoxycinnamoyl methyl reserpate	HMDB

Chemical Formula

C₃₅H₄₂N₂O₉

Average Molecular Weight

634.716

Monoisotopic Molecular Weight

634.289030952

IUPAC Name

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

Traditional Name

rescinnamine

CAS Registry Number

24815-24-5

SMILES

[H][C@]12C[C@@H](OC(=O)C=CC3=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/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/t20-,24+,26-,29-,31+,34+/m1/s1

InChI Key

SZLZWPPUNLXJEA-LAFLMMDJSA-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
Cinnamic acid or derivatives
Coumaric acid or derivatives
Cinnamic acid ester
3-alkylindole
Indole or derivatives
Indole
Styrene
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
Fatty acid ester
Alkyl aryl ether
Aralkylamine
Dicarboxylic acid or derivatives
Benzenoid
Monocyclic benzene moiety
Piperidine
Fatty acyl
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrole
Tertiary amine
Amino acid or derivatives
Tertiary aliphatic amine
Carboxylic acid ester
Carboxylic acid derivative
Ether
Azacycle
Dialkyl ether
Organoheterocyclic compound
Organic oxygen compound
Carbonyl group
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Organic nitrogen compound
Amine
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015311)
Membrane (HMDB: HMDB0015311)

Source

Exogenous

Exogenous (HMDB: HMDB0015311)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Rescinnamine Action Pathway (PathBank: SMP0000155)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	238.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0035 g/L	Not Available
LogP	3.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0035 g/L	ALOGPS
logP	4.48	ALOGPS
logP	4.07	ChemAxon
logS	-5.3	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	11	ChemAxon
Refractivity	171.16 m³·mol⁻¹	ChemAxon
Polarizability	69.65 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	260.777	30932474
DeepCCS	[M+Na]+	234.567	30932474
AllCCS	[M+H]+	248.9	32859911
AllCCS	[M+H-H2O]+	247.9	32859911
AllCCS	[M+NH4]+	249.8	32859911
AllCCS	[M+Na]+	250.0	32859911
AllCCS	[M-H]-	241.3	32859911
AllCCS	[M+Na-2H]-	244.5	32859911
AllCCS	[M+HCOO]-	248.0	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.	6.51 minutes	32390414
Predicted by Siyang on May 30, 2022	14.7284 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.33 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3142.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	181.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	247.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	174.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	147.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	657.7 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	593.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	460.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1257.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	635.5 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	1875.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	405.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	419.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	284.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	150.2 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	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Rescinnamine	[H][C@]12C[C@@H](OC(=O)C=CC3=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	6144.6	Standard polar	33892256
Rescinnamine	[H][C@]12C[C@@H](OC(=O)C=CC3=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	4670.9	Standard non polar	33892256
Rescinnamine	[H][C@]12C[C@@H](OC(=O)C=CC3=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	5190.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Rescinnamine,1TMS,isomer #1	COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C=CC2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C	4893.5	Semi standard non polar	33892256
Rescinnamine,1TMS,isomer #1	COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C=CC2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C	4811.0	Standard non polar	33892256
Rescinnamine,1TMS,isomer #1	COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C=CC2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C	6756.2	Standard polar	33892256
Rescinnamine,1TBDMS,isomer #1	COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C=CC2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C(C)(C)C	5025.0	Semi standard non polar	33892256
Rescinnamine,1TBDMS,isomer #1	COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C=CC2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C(C)(C)C	4988.0	Standard non polar	33892256
Rescinnamine,1TBDMS,isomer #1	COC(=O)[C@H]1[C@H]2C[C@@H]3C4=C(CCN3C[C@H]2C[C@@H](OC(=O)C=CC2=CC(OC)=C(OC)C(OC)=C2)[C@@H]1OC)C1=CC=C(OC)C=C1N4[Si](C)(C)C(C)(C)C	6665.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Rescinnamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-007p-0469134000-22e085a00ac52f1a3fc4	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 - Rescinnamine 10V, Positive-QTOF	splash10-0079-0033209000-ee873b6b010ae1decc8c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rescinnamine 20V, Positive-QTOF	splash10-00xs-0379405000-82705d2979450611dc45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rescinnamine 40V, Positive-QTOF	splash10-0pj0-3559003000-62945eb088df2981f749	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rescinnamine 10V, Negative-QTOF	splash10-001i-0031209000-69bd23b15cb07f5f5bc2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rescinnamine 20V, Negative-QTOF	splash10-0i0s-0258429000-07d3b407787494d1c141	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rescinnamine 40V, Negative-QTOF	splash10-000t-0549211000-fe6752c4b31c0e6bce52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rescinnamine 10V, Positive-QTOF	splash10-0079-0042009000-3f55aeb201794c3d5500	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rescinnamine 20V, Positive-QTOF	splash10-0079-0451019000-95ecd82537f2ede2cae9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rescinnamine 40V, Positive-QTOF	splash10-0ukd-0931021000-36cc3bd5905e4017f7cf	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rescinnamine 10V, Negative-QTOF	splash10-001i-0010009000-4efc2ba750ec5d3d3b4e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rescinnamine 20V, Negative-QTOF	splash10-00dr-0110094000-9f95afa9be8d5fe523c3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Rescinnamine 40V, Negative-QTOF	splash10-056a-1212191000-9673c536103f8fc8f464	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Rescinnamine Action Pathway		Not Available

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 DB01180	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01180	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01180

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00001762

Chemspider ID

30295

KEGG Compound ID

C06540

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rescinnamine

METLIN ID

Not Available

PubChem Compound

5280954

PDB ID

Not Available

ChEBI ID

28572

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. Angiotensin-converting enzyme

General function:: Involved in metallopeptidase activity
Specific function:: Converts angiotensin I to angiotensin II by release of the terminal His-Leu, this results in an increase of the vasoconstrictor activity of angiotensin. Also able to inactivate bradykinin, a potent vasodilator. Has also a glycosidase activity which releases GPI-anchored proteins from the membrane by cleaving the mannose linkage in the GPI moiety
Gene Name:: ACE
Uniprot ID:: P12821
Molecular weight:: 149713.7

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 ]
Azhar I, Mazhar F, Manzar QN, Hussain I, Shamim S: Colorimetric determination of indolic drugs. Pak J Pharm Sci. 2005 Apr;18(2):48-51. [PubMed:16431399 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Rescinnamine (HMDB0015311)

MOL for HMDB0015311 (Rescinnamine)

3D MOL for HMDB0015311 (Rescinnamine)

3D SDF for HMDB0015311 (Rescinnamine)

3D-SDF for HMDB0015311 (Rescinnamine)

PDB for HMDB0015311 (Rescinnamine)

3D PDB for HMDB0015311 (Rescinnamine)

SMILES for HMDB0015311 (Rescinnamine)

INCHI for HMDB0015311 (Rescinnamine)

Structure for HMDB0015311 (Rescinnamine)

3D Structure for HMDB0015311 (Rescinnamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References