NP-MRD: Showing NP-Card for Rhynchophylline (NP0050901)

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Record Information

Version

2.0

Created at

2022-04-27 22:22:19 UTC

Updated at

2022-04-27 22:22:19 UTC

NP-MRD ID

NP0050901

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rhynchophylline

Description

Rhynchophylline belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen. Rhynchophylline is found in Mitragyna africana, Mitragyna africanus WILLD., Mitragyna hirsuta, Mitragyna inermis , Mitragyna rotundifolia, Uncaria acida, Uncaria africana , Uncaria attenuata, Uncaria borneensis, Uncaria callophylla, Uncaria cordata, Uncaria elliptica, Uncaria guianensis , Uncaria hirsuta , Uncaria lancifolia, Uncaria longiflora, Uncaria macrophylla , Uncaria rhynchophylla , Uncaria sessilifructus , Uncaria sinensis and Uncaria tomentosa . Rhynchophylline was first documented in 2021 (PMID: 34870003). Based on a literature review a small amount of articles have been published on Rhynchophylline (PMID: 35468648) (PMID: 35400883) (PMID: 35380307) (PMID: 34738783).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200222D          

 28 31  0  0  1  0            999 V2000
    2.2974   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820   -0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820   -1.2195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974   -1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0425   -2.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -0.8070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3276   -0.1395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5429   -0.3945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5429   -1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3276   -1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0702    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    0.9645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8860    1.2195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4991    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575    2.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    2.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3402    2.3235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533    2.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8421    2.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137    3.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552    1.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399    1.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5117    1.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2963    1.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7390    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  1  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 13 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 23  1  6  0  0  0
 23 24  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
  1 28  1  0  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
   -4.0401    1.1944   -0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068    1.9808   -0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5749    1.4014   -0.7467 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4099    2.3501   -0.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3007    1.9236    0.7193 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3135    2.8629    1.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5450    2.0725    1.5275 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4016    0.8464    0.6136 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0772    1.1611   -0.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8720    2.0609   -1.4847 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1220    0.2004   -0.7887 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1163   -0.6909    0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9288   -1.7704    0.6640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7508   -2.4813    1.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7385   -2.1196    2.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9295   -1.0440    2.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1057   -0.3239    1.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9488    0.6593    0.5981 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3484   -0.0856   -0.5613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1746    0.0337   -0.3306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8897   -1.0954   -0.9083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856   -1.9651   -0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4923   -1.9081    1.2731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2681   -1.2017    2.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9835   -1.3451   -2.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4295   -0.5423   -3.1322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6550   -2.4241   -2.8531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7843   -2.7238   -4.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5619    1.0256    0.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8064    1.7991   -0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9258    0.2827   -1.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6539    2.2091    0.9241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9451    2.9922   -0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7114    1.3789   -1.8684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1806    2.4131   -1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208    3.3690   -0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5581    3.6175    0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9246    3.4412    2.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4654    2.6339    1.2967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4910    1.7752    2.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8014    0.1285   -1.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7276   -2.0335   -0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4233   -3.3172    1.9971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6266   -2.7076    3.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392   -0.8017    3.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873    0.0358    1.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208    0.3261   -1.5373 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5727   -1.1599   -0.4353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2796    0.0240    0.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0306   -2.8194   -0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2505   -0.1130    2.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0421   -1.4492    3.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3285   -1.5296    2.0298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8382   -2.7781   -4.5609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3261   -3.7414   -4.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -2.0274   -4.8486 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  1
  8 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 21 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 17  2  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
 20  3  1  0
 13 12  1  0
 18  5  1  0
 17  8  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  6
  4 35  1  0
  4 36  1  0
  6 37  1  0
  6 38  1  0
  7 39  1  0
  7 40  1  0
 18 46  1  1
 19 47  1  0
 19 48  1  0
 20 49  1  1
 22 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 28 54  1  0
 28 55  1  0
 28 56  1  0
 11 41  1  0
 16 45  1  0
 15 44  1  0
 14 43  1  0
 13 42  1  0
M  END


  Mrv1652304282200222D          

 28 31  0  0  1  0            999 V2000
    2.2974   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820   -0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820   -1.2195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974   -1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0425   -2.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -0.8070    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3276   -0.1395    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5429   -0.3945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5429   -1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3276   -1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0702    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    0.9645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8860    1.2195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4991    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575    2.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4444    2.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3402    2.3235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533    2.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8421    2.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0137    3.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4552    1.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2399    1.9843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5117    1.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2963    1.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7390    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  1  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 13 15  1  1  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 23  1  6  0  0  0
 23 24  1  0  0  0  0
  2 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
  1 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050901

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CN2CC[C@@]3([C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC)C(=O)NC1=C3C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22+/m0/s1

> <INCHI_KEY>
DAXYUDFNWXHGBE-KAXDATADSA-N

> <FORMULA>
C22H28N2O4

> <MOLECULAR_WEIGHT>
384.476

> <EXACT_MASS>
384.20490739

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.2043021815781

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-2-[(3R,6'R,7'S,8'aS)-6'-ethyl-2-oxo-1,2,3',5',6',7',8',8'a-octahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
2.6094639083333337

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.16702338486493

> <JCHEM_PKA_STRONGEST_BASIC>
10.712527798380334

> <JCHEM_POLAR_SURFACE_AREA>
67.87

> <JCHEM_REFRACTIVITY>
108.00600000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
rhynchophylline

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.289  -0.260   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.753  -0.736   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       5.753  -2.276   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.289  -2.752   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.813  -4.217   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.383  -1.506   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.478  -0.260   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.013  -0.736   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.013  -2.276   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.478  -2.752   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.131   0.294   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.189   1.800   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.654   2.276   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.798   1.246   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.974   3.783   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.830   4.813   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.635   4.337   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.779   5.368   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.439   4.259   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.759   5.765   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.583   3.228   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.048   3.704   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.955   2.831   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.420   2.355   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.898   0.294   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.577   1.800   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.113   2.276   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.968   1.246   0.000  0.00  0.00           C+0
CONECT    1    2    6   28                                                  
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    1    7   10                                             
CONECT    7    6    8   14                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   23                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    7                                                       
CONECT   15   13   16   19                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   15   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   12   24                                                       
CONECT   24   23                                                            
CONECT   25    2   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    1                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
Isorhynchophylline	MeSH
Isorhyncophylline	MeSH
Rhyncophylline	MeSH
Rhyncophylline, (16E)-isomer	MeSH
Rhyncophylline, (16E,20alpha)-isomer	MeSH

Chemical Formula

C₂₂H₂₈N₂O₄

Average Mass

384.4760 Da

Monoisotopic Mass

384.20491 Da

IUPAC Name

methyl (2E)-2-[(3R,6'R,7'S,8'aS)-6'-ethyl-2-oxo-1,2,3',5',6',7',8',8'a-octahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate

Traditional Name

rhynchophylline

CAS Registry Number

Not Available

SMILES

CC[C@H]1CN2CC[C@@]3([C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC)C(=O)NC1=C3C=CC=C1

InChI Identifier

InChI=1S/C22H28N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h5-8,13-15,19H,4,9-12H2,1-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22+/m0/s1

InChI Key

DAXYUDFNWXHGBE-KAXDATADSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mitragyna africana	Plant	KNApSAcK
Mitragyna africanus WILLD.	Plant	KNApSAcK
Mitragyna hirsuta	Plant	KNApSAcK
Mitragyna inermis	Plant	KNApSAcK
Mitragyna rotundifolia	Plant	KNApSAcK
Uncaria acida	Plant	KNApSAcK
Uncaria africana	Plant	KNApSAcK
Uncaria attenuata	Plant	KNApSAcK
Uncaria borneensis	Plant	KNApSAcK
Uncaria callophylla	Plant	KNApSAcK
Uncaria cordata	Plant	KNApSAcK
Uncaria elliptica	Plant	KNApSAcK
Uncaria guianensis	Plant	KNApSAcK
Uncaria hirsuta	Plant	KNApSAcK
Uncaria lancifolia	Plant	KNApSAcK
Uncaria longiflora	Plant	KNApSAcK
Uncaria macrophylla	Plant	KNApSAcK
Uncaria rhynchophylla	Plant	KNApSAcK
Uncaria sessilifructus	Plant	KNApSAcK
Uncaria sinensis	Plant	KNApSAcK
Uncaria tomentosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolizidines. These are polycyclic compounds containing an indolizidine, which is a bicyclic heterocycle containing a saturated six-member ring fused to a saturated five-member ring, one of the bridging atoms being nitrogen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indolizidines

Sub Class

Not Available

Direct Parent

Indolizidines

Alternative Parents

Substituents

Indole or derivatives
Dihydroindole
Indolizidine
Aralkylamine
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Lactam
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Amine
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indolizines (CHEBI:70069 )

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	2.85	ALOGPS
logP	2.61	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	13.17	ChemAxon
pKa (Strongest Basic)	10.71	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.87 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	108.01 m³·mol⁻¹	ChemAxon
Polarizability	42.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00001764

Chemspider ID

4444758

KEGG Compound ID

C09236

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rhynchophylline

METLIN ID

Not Available

PubChem Compound

5281408

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1098851

References

General References

Manwill PK, Flores-Bocanegra L, Khin M, Raja HA, Cech NB, Oberlies NH, Todd DA: Kratom (Mitragyna speciosa) Validation: Quantitative Analysis of Indole and Oxindole Alkaloids Reveals Chemotypes of Plants and Products. Planta Med. 2022 Apr 25. doi: 10.1055/a-1795-5876. [PubMed:35468648 ]
Wang XH, Li X, Qiang W, Yu XS, Zheng HJ, Zhang MS: Comparative transcriptome analysis revealed the molecular mechanism of the effect of light intensity on the accumulation of rhynchophylline and isorhynchophylline in Uncaria rhynchophylla. Physiol Mol Biol Plants. 2022 Feb;28(2):315-331. doi: 10.1007/s12298-022-01142-2. Epub 2022 Feb 20. [PubMed:35400883 ]
Li X, Wang XH, Qiang W, Zheng HJ, ShangGuan LY, Zhang MS: Transcriptome revealing the dual regulatory mechanism of ethylene on the rhynchophylline and isorhynchophylline in Uncaria rhynchophylla. J Plant Res. 2022 May;135(3):485-500. doi: 10.1007/s10265-022-01387-8. Epub 2022 Apr 5. [PubMed:35380307 ]
Yin T, Lu J, Liu Q, Zhu G, Zhang W, Jiang Z: Validated Quantitative (1)H NMR Method for Simultaneous Quantification of Indole Alkaloids in Uncaria rhynchophylla. ACS Omega. 2021 Nov 16;6(47):31810-31817. doi: 10.1021/acsomega.1c04464. eCollection 2021 Nov 30. [PubMed:34870003 ]
Fu WY, Hung KW, Lau SF, Butt B, Yuen VW, Fu G, Chan IC, Ip FCF, Fu AKY, Ip NY: Rhynchophylline Administration Ameliorates Amyloid-beta Pathology and Inflammation in an Alzheimer's Disease Transgenic Mouse Model. ACS Chem Neurosci. 2021 Nov 17;12(22):4249-4256. doi: 10.1021/acschemneuro.1c00600. Epub 2021 Nov 5. [PubMed:34738783 ]

Showing NP-Card for Rhynchophylline (NP0050901)

MOL for NP0050901 (Rhynchophylline)

3D MOL for NP0050901 (Rhynchophylline)

3D SDF for NP0050901 (Rhynchophylline)

3D-SDF for NP0050901 (Rhynchophylline)

PDB for NP0050901 (Rhynchophylline)

3D PDB for NP0050901 (Rhynchophylline)

SMILES for NP0050901 (Rhynchophylline)

INCHI for NP0050901 (Rhynchophylline)

Structure for NP0050901 (Rhynchophylline)

3D Structure for NP0050901 (Rhynchophylline)