NP-MRD: Showing NP-Card for (+/-)-Isorhynchophylline (NP0067436)

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Record Information

Version

2.0

Created at

2022-04-28 12:17:39 UTC

Updated at

2022-04-28 12:17:39 UTC

NP-MRD ID

NP0067436

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+/-)-Isorhynchophylline

Description

Isorhynchophylline 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. (+/-)-Isorhynchophylline is found in Hannoa klaineana, Mitragyna africanus WILLD., Mitragyna brunonis Craib, Mitragyna hirsuta, Mitragyna hirsuta Havil, Mitragyna inermis, Mitragyna speciosa, Mitragyna speciosa Korth., Uncaria acida, Uncaria africana , Uncaria attenuata, Uncaria borneensis, Uncaria callophylla, Uncaria cordata, Uncaria elliptica, Uncaria guianensis , Uncaria longiflora, Uncaria macrophylla, Uncaria macrophylla Wall. , Uncaria rhynchophylla , Uncaria rhynchophyllus, Uncaria sessilifructus , Uncaria sinensis and Uncaria tomentosa . (+/-)-Isorhynchophylline was first documented in 2022 (PMID: 35469836). Based on a literature review a small amount of articles have been published on Isorhynchophylline (PMID: 35400883) (PMID: 35380307) (PMID: 35250597) (PMID: 35096110).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282214172D          

 28 31  0  0  1  0            999 V2000
    4.4813   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8169    0.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3320    1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5115    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1759    0.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608   -0.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3554    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1839    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302    1.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984    1.6320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    0.4987    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1994   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270   -0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3789   -0.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060    0.3263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2295    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0500    1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2554    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0759    1.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4114    0.9075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2319    0.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802    2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047    3.1685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007    2.5873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2362    3.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9265    0.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -0.5136    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 17 19  1  1  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 16 27  1  6  0  0  0
 27 28  1  0  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
   -2.1518   -1.2618   -3.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4944   -1.9226   -1.7481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4780   -1.6652   -0.6456 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1769   -2.2176   -1.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6891   -1.2920   -1.8277 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9497   -1.8467   -2.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9485   -1.3032   -1.2184 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3754    0.0813   -0.9491 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8391    1.0416   -2.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6476    0.8622   -3.2232 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900    2.1083   -1.3435 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4958    1.8499    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0450    2.6083    1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9759    2.1820    2.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3545    0.9892    2.6595 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8095    0.2427    1.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8661    0.6496    0.3072 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9127   -0.0866   -1.0762 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1201   -0.0867    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3471   -0.2538   -0.2753 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2618    0.3595    0.6601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274   -0.2394    1.3079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5353   -1.5778    1.2022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8164   -2.2871    2.3881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1350    1.8080    0.9036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610    2.4927    0.3340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9676    2.5002    1.7713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8464    3.8783    2.0025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0599   -1.9970   -3.8875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9831   -0.5964   -3.3334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2494   -0.6208   -3.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4383   -3.0369   -1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5250   -1.7181   -1.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7542   -2.3784    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3839   -2.6496   -0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3800   -3.0823   -1.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9641   -2.9357   -2.3009 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2135   -1.4306   -3.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0211   -1.9201   -0.3208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9367   -1.1632   -1.6822 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904    2.9400   -1.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5459    3.5630    0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4161    2.7990    3.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921    0.6384    3.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3374   -0.7011    1.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4926    0.7496   -1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2012    0.8504    0.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2745   -0.9857    0.8313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4003    0.3488   -1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8629    0.3490    2.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9178   -2.2215    3.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6194   -1.7353    2.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1741   -3.3102    2.2116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8298    4.3593    1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5345    3.9900    3.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0607    4.2821    1.3425 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  6
  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 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 20  3  1  0
 17 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  1
  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  6
 19 47  1  0
 19 48  1  0
 20 49  1  6
 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
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
M  END


  Mrv1652304282214172D          

 28 31  0  0  1  0            999 V2000
    4.4813   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8169    0.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3320    1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5115    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1759    0.3263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6608   -0.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3554    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1839    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4302    1.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984    1.6320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    0.4987    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1994   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5270   -0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3789   -0.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060    0.3263    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2295    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0500    1.1662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2554    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0759    1.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4114    0.9075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2319    0.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0802    2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047    3.1685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007    2.5873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2362    3.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9265    0.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2620   -0.5136    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 17 19  1  1  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 16 27  1  6  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067436

> <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=CC=CC=C31

> <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-VKCGGMIFSA-N

> <FORMULA>
C22H28N2O4

> <MOLECULAR_WEIGHT>
384.476

> <EXACT_MASS>
384.20490739

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.61414902873591

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-2-[(3S,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>
108.00599999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.40e-02 g/l

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

> <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       8.365  -0.476   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.991   0.931   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.086   2.177   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.555   2.016   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.928   0.609   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.834  -0.637   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.397   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.077   2.276   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.670   2.903   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       5.410   3.046   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.865   0.931   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.239  -0.476   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.383  -1.506   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.717  -0.736   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.707  -0.637   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.198   0.609   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.428   2.016   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.960   2.177   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.477   3.262   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.008   3.101   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.635   1.694   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.166   1.533   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.150   4.669   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.756   5.915   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.681   4.830   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.308   6.236   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.729   0.448   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.356  -0.959   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   11   14                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4                                                       
CONECT   11    7   12   18                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17   27                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   11                                                       
CONECT   19   17   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   19   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
CONECT   27   16   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
Isorhyncophylline	MeSH
Rhynchophylline	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-[(3S,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

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

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=CC=CC=C31

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-VKCGGMIFSA-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
Hannoa klaineana	LOTUS Database	35616633
Mitragyna africanus WILLD.	Plant	KNApSAcK
Mitragyna brunonis Craib	Plant	KNApSAcK
Mitragyna hirsuta	LOTUS Database	35616633
Mitragyna hirsuta Havil	Plant	KNApSAcK
Mitragyna inermis	LOTUS Database	35616633
Mitragyna speciosa	LOTUS Database	35616633
Mitragyna speciosa Korth.	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 longiflora	Plant	KNApSAcK
Uncaria macrophylla	LOTUS Database	35616633
Uncaria macrophylla Wall.	Plant	KNApSAcK
Uncaria rhynchophylla	Plant	KNApSAcK
Uncaria rhynchophyllus	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:70071 )

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	41.61 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

C00050990

Chemspider ID

2300899

KEGG Compound ID

C16980

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3037048

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li Z, Shi H, Li Y, Wang W, Li Z, Chen B, Nie D: Isorhynchophylline ameliorates the progression of osteoarthritis by inhibiting the NF-kappaB pathway. Eur J Pharmacol. 2022 Jun 5;924:174971. doi: 10.1016/j.ejphar.2022.174971. Epub 2022 Apr 22. [PubMed:35469836 ]
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 ]
Qin R, Zhao Q, Han B, Zhu HP, Peng C, Zhan G, Huang W: Indole-Based Small Molecules as Potential Therapeutic Agents for the Treatment of Fibrosis. Front Pharmacol. 2022 Feb 16;13:845892. doi: 10.3389/fphar.2022.845892. eCollection 2022. [PubMed:35250597 ]
He Z, Wang J, Wang X, Dong Y: The Study of the Transport Mechanism of Isorhynchophylline in Liver. Evid Based Complement Alternat Med. 2022 Jan 19;2022:3867323. doi: 10.1155/2022/3867323. eCollection 2022. [PubMed:35096110 ]

Showing NP-Card for (+/-)-Isorhynchophylline (NP0067436)

MOL for NP0067436 ((+/-)-Isorhynchophylline)

3D MOL for NP0067436 ((+/-)-Isorhynchophylline)

3D SDF for NP0067436 ((+/-)-Isorhynchophylline)

3D-SDF for NP0067436 ((+/-)-Isorhynchophylline)

PDB for NP0067436 ((+/-)-Isorhynchophylline)

3D PDB for NP0067436 ((+/-)-Isorhynchophylline)

SMILES for NP0067436 ((+/-)-Isorhynchophylline)

INCHI for NP0067436 ((+/-)-Isorhynchophylline)

Structure for NP0067436 ((+/-)-Isorhynchophylline)

3D Structure for NP0067436 ((+/-)-Isorhynchophylline)