NP-MRD: Showing NP-Card for methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate (NP0143899)

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Record Information

Version

2.0

Created at

2022-09-01 22:45:15 UTC

Updated at

2022-09-01 22:45:15 UTC

NP-MRD ID

NP0143899

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate

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. methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate is found in Uncaria tomentosa. methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate was first documented in 2022 (PMID: 35468648). Based on a literature review a small amount of articles have been published on Rhynchophylline (PMID: 35400883) (PMID: 35926328) (PMID: 35691093) (PMID: 35517784).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022200452D          

 28 31  0  0  1  0            999 V2000
    0.8517    0.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363   -0.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2494    0.3170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0779    1.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    1.6761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4756    2.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9605    2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455    2.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1905    3.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    2.5011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8432    1.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6716    0.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8870    0.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739    0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455    1.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4756    1.4211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6471    0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0340    0.0621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2056   -0.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9902   -0.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6033   -0.4478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3879   -0.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5925   -1.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7640   -2.1039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079   -1.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1948   -1.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  8 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18  5  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  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
   -1.7971    3.8983   -0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6576    2.7078    0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292    1.4361   -0.4160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1132    1.6854   -1.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9498    1.7223   -0.2749 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1181    2.4105   -0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1562    1.6801    0.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4556    0.4187    0.8154 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8047    0.0928    2.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532    0.9222    3.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2788   -1.0993    2.2253 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3073   -1.6875    0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7361   -2.9345    0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6524   -3.2558   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1528   -2.3650   -1.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -1.1334   -1.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8012   -0.7630    0.0420 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000    0.8008    0.7678 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1033   -0.3707    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3139    0.2159    0.4392 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3520   -0.7835    0.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1136   -2.0119   -0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8466   -2.4175   -0.4159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805   -3.3507   -1.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7441   -0.4748    0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1024    0.6446    0.9818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7626   -1.4238    0.4561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0967   -1.1012    0.7535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8071    4.3652   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4731    4.6272   -0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1749    3.5589   -1.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4954    2.6234    1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328    2.8741    0.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2430    1.3545   -1.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2166    2.6441   -1.7082 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0018    0.8805   -1.9172 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0448    3.4592   -0.1126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4370    2.5128   -1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4683    2.2578    1.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0029    1.4362   -0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2945    1.7179    3.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1278   -3.6263    1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9835   -4.2254   -1.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0987   -2.6475   -2.8032 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3482   -0.4440   -2.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6477    1.2106    1.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4137   -0.6431   -0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1531   -1.1517    1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3938    0.5928    1.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9520   -2.7389   -0.2112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0639   -2.9425   -2.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3731   -3.6863   -1.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865   -4.2753   -1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2411   -0.8020    1.8264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5223   -0.3486    0.0653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6900   -2.0465    0.5881 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
  7  8  1  0
  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  1
  9 10  1  0
  9 11  2  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  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
 10 41  1  0
 13 42  1  0
 14 43  1  0
 15 44  1  0
 16 45  1  0
M  END


  Mrv1652309022200452D          

 28 31  0  0  1  0            999 V2000
    0.8517    0.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363   -0.2350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2494    0.3170    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0779    1.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    1.6761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4756    2.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9605    2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455    2.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1905    3.5406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    2.5011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8432    1.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6716    0.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8870    0.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739    0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455    1.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4756    1.4211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6471    0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0340    0.0621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2056   -0.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9902   -0.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6033   -0.4478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3879   -0.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5925   -1.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7640   -2.1039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8079   -1.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1948   -1.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  8 17  1  0  0  0  0
  8 18  1  0  0  0  0
 18  5  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 21 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0143899

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CN2CCC3([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-GXONQVTISA-N

> <FORMULA>
C22H28N2O4

> <MOLECULAR_WEIGHT>
384.476

> <EXACT_MASS>
384.20490739

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.23968646430233

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
0.6058954905871892

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.710993834303773

> <JCHEM_PKA_STRONGEST_BASIC>
11.148658222044512

> <JCHEM_POLAR_SURFACE_AREA>
71.36

> <JCHEM_REFRACTIVITY>
108.76109999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.80e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.590   0.037   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.054  -0.439   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.199   0.592   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.879   2.098   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       5.023   3.129   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.023   4.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.488   5.145   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.393   3.899   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.298   5.145   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.822   6.609   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       9.763   4.669   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.763   3.129   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.907   2.098   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.587   0.592   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.122   0.116   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.978   1.146   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.298   2.653   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.488   2.653   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.808   1.146   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.664   0.116   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.984  -1.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.448  -1.866   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.593  -0.836   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.057  -1.312   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.839  -2.421   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.159  -3.927   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       3.375  -1.945   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.230  -2.975   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17   18                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12    8                                                  
CONECT   18    8    5   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   21   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   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
Isorhynchophylline	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-[(6'R,7'S,8'aS)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC[C@H]1CN2CCC3([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-GXONQVTISA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Uncaria tomentosa	LOTUS Database	35616633

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
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Lactam
Carboxylic acid ester
Azacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Amine
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
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	2.81	ALOGPS
logP	0.61	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	11.15	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	71.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	108.76 m³·mol⁻¹	ChemAxon
Polarizability	42.24 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

57256878

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Rhynchophylline

METLIN ID

Not Available

PubChem Compound

102004527

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

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 ]
Zhang X, Wang S, Shu L, Zhao S, Yan X, Jia G, Zhang Y, Zhang W, Qian W, Yang B, Li Y: Rapid screening of hepatotoxic components in Uncariae Ramulus Cum Uncis based on "component-target-pathway" network. J Pharm Biomed Anal. 2022 Sep 20;219:114968. doi: 10.1016/j.jpba.2022.114968. Epub 2022 Jul 26. [PubMed:35926328 ]
Jiang S, Yang X, Wang Z, Gan C, Huang J, Sun J, Peng H, Wei F, Wang Z, Yang C: Biotransformation and pharmacokinetic studies of four alkaloids from Uncaria rhynchophylla in rat plasma by ultra-performance liquid chromatography with tandem mass spectrometry. J Pharm Biomed Anal. 2022 Sep 5;218:114858. doi: 10.1016/j.jpba.2022.114858. Epub 2022 Jun 2. [PubMed:35691093 ]
Liu J, Zhao Y, Zhu Y, Wang Y, Liu X, Nie X, Zhao J, Wang W, Cheng J: Rhynchophylline Regulates Calcium Homeostasis by Antagonizing Ryanodine Receptor 2 Phosphorylation to Improve Diabetic Cardiomyopathy. Front Pharmacol. 2022 Apr 19;13:882198. doi: 10.3389/fphar.2022.882198. eCollection 2022. [PubMed:35517784 ]
LOTUS database [Link]

Showing NP-Card for methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate (NP0143899)

MOL for NP0143899 (methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

3D MOL for NP0143899 (methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

3D SDF for NP0143899 (methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

3D-SDF for NP0143899 (methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

PDB for NP0143899 (methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

3D PDB for NP0143899 (methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

SMILES for NP0143899 (methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

INCHI for NP0143899 (methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

Structure for NP0143899 (methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

3D Structure for NP0143899 (methyl (2e)-2-[(6'r,7's,8'as)-6'-ethyl-2-hydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)