NP-MRD: Showing NP-Card for isorauhimbinic acid (NP0028223)

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Record Information

Version

2.0

Created at

2021-06-19 20:10:37 UTC

Updated at

2021-06-29 23:54:52 UTC

NP-MRD ID

NP0028223

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isorauhimbinic acid

Provided By

JEOL Database JEOL Logo

Description

Isorauhimbinic acid is also known as isorauhimbinate. isorauhimbinic acid is found in Rauwolfia serpentina. isorauhimbinic acid was first documented in 2005 (PMID: 15974606). Based on a literature review very few articles have been published on Isorauhimbinic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122103D          

 49 53  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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  Mrv1652306192122103D          

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  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
 16 15  1  0  0  0  0
  9 34  1  1  0  0  0
 14 13  1  0  0  0  0
  4  2  1  0  0  0  0
 15 23  1  0  0  0  0
  2  1  2  0  0  0  0
 11 12  1  0  0  0  0
  2  3  1  0  0  0  0
 12 13  1  0  0  0  0
  5  6  1  0  0  0  0
 11 23  1  0  0  0  0
 25 49  1  6  0  0  0
 21 20  2  0  0  0  0
 23 46  1  6  0  0  0
 16 41  1  0  0  0  0
 21 45  1  0  0  0  0
 20 44  1  0  0  0  0
 19 43  1  0  0  0  0
 18 42  1  0  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 13 39  1  0  0  0  0
 13 40  1  0  0  0  0
 24 47  1  0  0  0  0
 24 48  1  0  0  0  0
 10 35  1  0  0  0  0
 10 36  1  0  0  0  0
  4 27  1  1  0  0  0
  5 28  1  6  0  0  0
  7 30  1  0  0  0  0
  7 31  1  0  0  0  0
  8 32  1  0  0  0  0
  8 33  1  0  0  0  0
  3 26  1  0  0  0  0
  6 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028223

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]1([H])[C@@]([H])(O[H])C([H])([H])C([H])([H])[C@]2([H])C([H])([H])N3C([H])([H])C([H])([H])C4=C(N([H])C5=C4C([H])=C([H])C([H])=C5[H])[C@@]3([H])C([H])([H])[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H24N2O3/c23-17-6-5-11-10-22-8-7-13-12-3-1-2-4-15(12)21-19(13)16(22)9-14(11)18(17)20(24)25/h1-4,11,14,16-18,21,23H,5-10H2,(H,24,25)/t11-,14+,16-,17+,18+/m1/s1

> <INCHI_KEY>
AADVZSXPNRLYLV-IIIYPXSQSA-N

> <FORMULA>
C20H24N2O3

> <MOLECULAR_WEIGHT>
340.423

> <EXACT_MASS>
340.178692641

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
37.29743881079996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,15S,18S,19S,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylic acid

> <ALOGPS_LOGP>
2.00

> <JCHEM_LOGP>
-0.6580596687910913

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.945294885630464

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0802821262615625

> <JCHEM_PKA_STRONGEST_BASIC>
7.335153937226922

> <JCHEM_POLAR_SURFACE_AREA>
76.56

> <JCHEM_REFRACTIVITY>
94.8619

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,15S,18S,19S,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
   -2.0704    4.0763    2.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8569    3.7275    3.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9546    4.5983    4.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496    2.2940    3.6327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4835    2.2100    4.7337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9467    2.9445    5.8794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2376    0.7606    5.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0968   -0.1545    3.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9598   -0.0567    2.8729 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6044   -0.9404    1.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564   -0.4449    0.9068 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8429   -1.3193   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2351   -1.3435   -1.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8388    0.0076   -1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5647    1.0398   -0.6940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2971    2.1297   -1.0815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0372    1.8185   -2.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9265    2.6100   -2.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5529    2.0253   -4.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3011    0.7007   -4.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4117   -0.0795   -3.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7650    0.4878   -2.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930    0.9645    0.4594 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0486    1.8879    1.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1861    1.4018    2.4223 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7617    4.1583    5.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5014    1.9278    4.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4506    2.6822    4.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146    2.7703    6.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1259    0.3787    5.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5708    0.7252    5.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556   -1.1890    4.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0949    0.0951    3.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9060   -0.4342    3.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908   -1.9548    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4966   -1.0203    1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920   -0.9821   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0339   -2.3448    0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0278   -2.0511   -1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2161   -1.6924   -2.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258    3.0263   -0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1278    3.6405   -2.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2490    2.6149   -4.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8009    0.2663   -5.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2238   -1.1115   -3.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677    1.2999    0.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0920    2.9095    1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    1.9401    2.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0468    1.4128    1.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 22  1  0
 20 19  1  0
 11 10  1  0
 23 24  1  0
 24 25  1  0
  9 10  1  0
  9 25  1  0
 19 18  2  0
 18 17  1  0
 14 15  2  0
 17 22  2  0
 17 16  1  0
 22 21  1  0
  9  8  1  0
 25  4  1  0
  4  5  1  0
  5  7  1  0
  7  8  1  0
 16 15  1  0
  9 34  1  1
 14 13  1  0
  4  2  1  0
 15 23  1  0
  2  1  2  0
 11 12  1  0
  2  3  1  0
 12 13  1  0
  5  6  1  0
 11 23  1  0
 25 49  1  6
 21 20  2  0
 23 46  1  6
 16 41  1  0
 21 45  1  0
 20 44  1  0
 19 43  1  0
 18 42  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 24 47  1  0
 24 48  1  0
 10 35  1  0
 10 36  1  0
  4 27  1  1
  5 28  1  6
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  3 26  1  0
  6 29  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.070   4.076   2.052  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.857   3.728   3.205  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.955   4.598   4.236  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.550   2.294   3.633  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.484   2.210   4.734  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.947   2.945   5.879  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.238   0.761   5.160  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.097  -0.155   3.987  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.960  -0.057   2.873  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.604  -0.940   1.663  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.556  -0.445   0.907  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.843  -1.319  -0.265  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.235  -1.343  -1.385  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.839   0.008  -1.570  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.565   1.040  -0.694  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.297   2.130  -1.081  0.00  0.00           N+0
HETATM   17  C   UNK     0      -2.037   1.819  -2.204  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.926   2.610  -2.940  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.553   2.025  -4.045  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.301   0.701  -4.396  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.412  -0.080  -3.648  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.765   0.488  -2.533  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.393   0.965   0.459  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.049   1.888   1.635  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.186   1.402   2.422  0.00  0.00           C+0
HETATM   26  H   UNK     0      -1.762   4.158   5.101  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.501   1.928   4.046  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.451   2.682   4.411  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.315   2.770   6.605  0.00  0.00           H+0
HETATM   30  H   UNK     0      -1.126   0.379   5.681  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.571   0.725   5.901  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.156  -1.189   4.347  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.095   0.095   3.610  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.906  -0.434   3.286  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.391  -1.955   2.023  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.497  -1.020   1.030  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.792  -0.982  -0.705  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.034  -2.345   0.075  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.028  -2.051  -1.114  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.216  -1.692  -2.320  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.326   3.026  -0.612  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.128   3.640  -2.666  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.249   2.615  -4.637  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.801   0.266  -5.258  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.224  -1.111  -3.926  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.368   1.300   0.077  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.092   2.910   1.269  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.922   1.940   2.296  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.047   1.413   1.739  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    4    1    3                                                  
CONECT    3    2   26                                                       
CONECT    4   25    5    2   27                                             
CONECT    5    4    7    6   28                                             
CONECT    6    5   29                                                       
CONECT    7    5    8   30   31                                             
CONECT    8    9    7   32   33                                             
CONECT    9   10   25    8   34                                             
CONECT   10   11    9   35   36                                             
CONECT   11   10   12   23                                                  
CONECT   12   11   13   37   38                                             
CONECT   13   14   12   39   40                                             
CONECT   14   22   15   13                                                  
CONECT   15   14   16   23                                                  
CONECT   16   17   15   41                                                  
CONECT   17   18   22   16                                                  
CONECT   18   19   17   42                                                  
CONECT   19   20   18   43                                                  
CONECT   20   19   21   44                                                  
CONECT   21   22   20   45                                                  
CONECT   22   14   17   21                                                  
CONECT   23   24   15   11   46                                             
CONECT   24   23   25   47   48                                             
CONECT   25   24    9    4   49                                             
CONECT   26    3                                                            
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    6                                                            
CONECT   30    7                                                            
CONECT   31    7                                                            
CONECT   32    8                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   10                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   13                                                            
CONECT   40   13                                                            
CONECT   41   16                                                            
CONECT   42   18                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
CONECT   45   21                                                            
CONECT   46   23                                                            
CONECT   47   24                                                            
CONECT   48   24                                                            
CONECT   49   25                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  106    0
END

RDKit          3D

49 53  0  0  0  0  0  0  0  0999 V2000
   -2.0704    4.0763    2.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8569    3.7275    3.2054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9546    4.5983    4.2356 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5496    2.2940    3.6327 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4835    2.2100    4.7337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9467    2.9445    5.8794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2376    0.7606    5.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0968   -0.1545    3.9874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9598   -0.0567    2.8729 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6044   -0.9404    1.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5564   -0.4449    0.9068 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8429   -1.3193   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2351   -1.3435   -1.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8388    0.0076   -1.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5647    1.0398   -0.6940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2971    2.1297   -1.0815 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0372    1.8185   -2.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9265    2.6100   -2.9403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5529    2.0253   -4.0451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3011    0.7007   -4.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4117   -0.0795   -3.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7650    0.4878   -2.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930    0.9645    0.4594 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0486    1.8879    1.6346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1861    1.4018    2.4223 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7617    4.1583    5.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5014    1.9278    4.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4506    2.6822    4.4107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3146    2.7703    6.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1259    0.3787    5.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5708    0.7252    5.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556   -1.1890    4.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0949    0.0951    3.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9060   -0.4342    3.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908   -1.9548    2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4966   -1.0203    1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920   -0.9821   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0339   -2.3448    0.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0278   -2.0511   -1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2161   -1.6924   -2.3203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3258    3.0263   -0.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1278    3.6405   -2.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2490    2.6149   -4.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8009    0.2663   -5.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2238   -1.1115   -3.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677    1.2999    0.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0920    2.9095    1.2688 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    1.9401    2.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0468    1.4128    1.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 22  1  0
 20 19  1  0
 11 10  1  0
 23 24  1  0
 24 25  1  0
  9 10  1  0
  9 25  1  0
 19 18  2  0
 18 17  1  0
 14 15  2  0
 17 22  2  0
 17 16  1  0
 22 21  1  0
  9  8  1  0
 25  4  1  0
  4  5  1  0
  5  7  1  0
  7  8  1  0
 16 15  1  0
  9 34  1  1
 14 13  1  0
  4  2  1  0
 15 23  1  0
  2  1  2  0
 11 12  1  0
  2  3  1  0
 12 13  1  0
  5  6  1  0
 11 23  1  0
 25 49  1  6
 21 20  2  0
 23 46  1  6
 16 41  1  0
 21 45  1  0
 20 44  1  0
 19 43  1  0
 18 42  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 13 40  1  0
 24 47  1  0
 24 48  1  0
 10 35  1  0
 10 36  1  0
  4 27  1  1
  5 28  1  6
  7 30  1  0
  7 31  1  0
  8 32  1  0
  8 33  1  0
  3 26  1  0
  6 29  1  0
M  END

View in JSmol

Synonyms

Value	Source
Isorauhimbinate	Generator

Chemical Formula

C₂₀H₂₄N₂O₃

Average Mass

340.4230 Da

Monoisotopic Mass

340.17869 Da

IUPAC Name

(1R,15S,18S,19S,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylic acid

Traditional Name

(1R,15S,18S,19S,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@]1([H])[C@@]([H])(O[H])C([H])([H])C([H])([H])[C@]2([H])C([H])([H])N3C([H])([H])C([H])([H])C4=C(N([H])C5=C4C([H])=C([H])C([H])=C5[H])[C@@]3([H])C([H])([H])[C@]12[H]

InChI Identifier

InChI=1S/C20H24N2O3/c23-17-6-5-11-10-22-8-7-13-12-3-1-2-4-15(12)21-19(13)16(22)9-14(11)18(17)20(24)25/h1-4,11,14,16-18,21,23H,5-10H2,(H,24,25)/t11-,14+,16-,17+,18+/m1/s1

InChI Key

AADVZSXPNRLYLV-IIIYPXSQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rauvolfia serpentina	JEOL database	Itoh, A., et al, J. Nat. Prod. 68, 848 (2005)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as corynanthean-type alkaloids. These are alkaloids with a structure based on the corynanthean nucleus, which is a tetracycle characterized by an indole fused to a quinolizidine. Additionally, the quinolizidine ring system is substituted to a 2-methylpropyl group and one ethyl group.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Corynanthean-type alkaloids

Sub Class

Not Available

Direct Parent

Corynanthean-type alkaloids

Alternative Parents

Substituents

Corynanthean skeleton
Beta-carboline
Pyridoindole
3-alkylindole
Indole or derivatives
Indole
Beta-hydroxy acid
Aralkylamine
Piperidine
Hydroxy acid
Benzenoid
Cyclic alcohol
Pyrrole
Heteroaromatic compound
Secondary alcohol
Amino acid
Tertiary amine
Tertiary aliphatic amine
Amino acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Amine
Alcohol
Carbonyl group
Organopnictogen compound
Organic nitrogen compound
Organooxygen compound
Organic oxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2	ALOGPS
logP	-0.66	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	4.08	ChemAxon
pKa (Strongest Basic)	7.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	76.56 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.86 m³·mol⁻¹	ChemAxon
Polarizability	37.3 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24693348

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12304067

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Itoh A, Kumashiro T, Yamaguchi M, Nagakura N, Mizushina Y, Nishi T, Tanahashi T: Indole alkaloids and other constituents of Rauwolfia serpentina. J Nat Prod. 2005 Jun;68(6):848-52. doi: 10.1021/np058007n. [PubMed:15974606 ]
Itoh, A., et al. (2005). Itoh, A., et al, J. Nat. Prod. 68, 848 (2005). J. Nat. Prod..

Showing NP-Card for isorauhimbinic acid (NP0028223)

MOL for NP0028223 (isorauhimbinic acid)

3D MOL for NP0028223 (isorauhimbinic acid)

3D SDF for NP0028223 (isorauhimbinic acid)

3D-SDF for NP0028223 (isorauhimbinic acid)

PDB for NP0028223 (isorauhimbinic acid)

3D PDB for NP0028223 (isorauhimbinic acid)

SMILES for NP0028223 (isorauhimbinic acid)

INCHI for NP0028223 (isorauhimbinic acid)

Structure for NP0028223 (isorauhimbinic acid)

3D Structure for NP0028223 (isorauhimbinic acid)