NP-MRD: Showing NP-Card for Geissoschizine methyl ether (NP0137253)

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Record Information

Version

2.0

Created at

2022-05-30 16:46:42 UTC

Updated at

2022-05-30 16:46:42 UTC

NP-MRD ID

NP0137253

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Geissoschizine methyl ether

Description

Geissoschizine methyl ether 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. Geissoschizine methyl ether is found in Uncaria rhynchophylla and Uncaria sinensis. Geissoschizine methyl ether was first documented in 2020 (PMID: 32350314). Based on a literature review a small amount of articles have been published on Geissoschizine methyl ether (PMID: 34335255) (PMID: 32898626) (PMID: 32004630) (PMID: 31911638).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305302218462D          

 27 30  0  0  0  0            999 V2000
    7.3488   -1.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5252   -1.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0725   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2489   -0.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909    1.1022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801   -0.3254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8779   -1.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -1.7510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3305   -2.3936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9595   -3.1304    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  4  0  0  0
  3  4  2  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 14 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  4  0  0  0
  4 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
    2.0287   -3.2991    2.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4331   -2.0833    1.8746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5115   -1.1813    1.5101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1258   -1.4654    1.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637   -0.9344    1.0793 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7830   -1.8723    0.5540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7367   -1.2746   -0.4588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8718    0.1968   -0.3528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7189    0.9100   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0483    2.2110   -0.0031 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3637    2.3608   -0.2661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2134    3.4416   -0.3494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5634    3.2731   -0.6474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0876    2.0178   -0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2575    0.9349   -0.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9217    1.1038   -0.4935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5196    0.0697    0.1351 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6464    0.9103    0.6212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8794    0.0394    0.7705 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5142   -0.2184   -0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6874   -1.4280   -1.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2904   -1.6285   -2.2749 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5330   -2.3234   -2.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9867    0.9099   -1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5437    0.7126   -2.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8939    2.2368   -0.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3746    3.2862   -1.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8986   -3.8695    2.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4309   -3.9939    1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4414   -2.9803    3.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4910   -1.9664    1.6478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0177   -2.5608    2.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0115   -0.9644    2.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879   -2.3087    1.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135   -2.6747    0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3827   -1.5207   -1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7090   -1.7911   -0.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747    2.9803    0.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8517    4.4441   -0.1855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2304    4.1180   -0.7132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1354    1.9299   -1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6140   -0.0756   -0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2997   -0.4061   -0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8437    1.6324   -0.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3823    1.4729    1.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5784    0.6168    1.4437 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3824   -2.3167   -0.5190 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4712   -3.3449   -1.9343 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2891   -1.7138   -1.7849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8720   -2.3219   -3.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6845    4.1729   -1.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6414    3.5850   -2.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2989    2.9513   -2.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 21  1  0
 21 20  2  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
 20 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
  3 19  1  0
  9 17  1  0
 16 11  1  0
 16  8  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 21 47  1  0
 19 46  1  1
 18 44  1  0
 18 45  1  0
 17 43  1  6
  6 34  1  0
  6 35  1  0
  7 36  1  0
  7 37  1  0
 10 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 15 42  1  0
  4 32  1  0
  4 33  1  0
  2 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 27 51  1  0
 27 52  1  0
 27 53  1  0
M  END


  Mrv1652305302218462D          

 27 30  0  0  0  0            999 V2000
    7.3488   -1.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5252   -1.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0725   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2489   -0.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7962   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5199    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8909    1.1022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6146    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2436    1.0079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6962    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1801   -0.3254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4085   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6753   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0188    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7537    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4477    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7145    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1672    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4435   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8779   -1.7038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -1.7510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3305   -2.3936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9595   -3.1304    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  4  0  0  0
  3  4  2  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
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 11 19  1  0  0  0  0
 14 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  4  0  0  0
  4 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137253

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC=C(C1CC2N(CCC3=C2NC2=CC=CC=C32)CC1=CC)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H26N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h4-8,13,17,20,23H,9-12H2,1-3H3

> <INCHI_KEY>
VAMJZLUOKJRHOW-UHFFFAOYSA-N

> <FORMULA>
C22H26N2O3

> <MOLECULAR_WEIGHT>
366.461

> <EXACT_MASS>
366.194342705

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
41.99052936497706

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-{3-ethylidene-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl}-3-methoxyprop-2-enoate

> <JCHEM_LOGP>
3.129639101

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.374071556130772

> <JCHEM_PKA_STRONGEST_BASIC>
6.341787620823784

> <JCHEM_POLAR_SURFACE_AREA>
54.559999999999995

> <JCHEM_REFRACTIVITY>
107.22300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-{3-ethylidene-1H,2H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl}-3-methoxyprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-MAY-22         0                                  
HETATM    1  C   UNK     0      13.718  -2.916   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.180  -3.004   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.335  -1.717   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.798  -1.805   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.953  -0.517   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.415  -0.606   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.570   0.682   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       7.263   2.057   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       6.418   3.345   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.881   3.257   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.188   1.881   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.033   0.594   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       4.070  -0.607   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.629  -0.063   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.260  -0.768   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.035   0.064   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.038   1.603   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.407   2.308   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.702   1.476   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.800   2.146   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.645   0.858   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.183   0.946   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.028  -0.341   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.105  -3.180   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.568  -3.269   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.950  -4.468   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.258  -5.843   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   24                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   11   14                                                  
CONECT   20    8   21                                                       
CONECT   21   20    5   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24    4   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₆N₂O₃

Average Mass

366.4610 Da

Monoisotopic Mass

366.19434 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC=C(C1CC2N(CCC3=C2NC2=CC=CC=C32)CC1=CC)C(=O)OC

InChI Identifier

InChI=1S/C22H26N2O3/c1-4-14-12-24-10-9-16-15-7-5-6-8-19(15)23-21(16)20(24)11-17(14)18(13-26-2)22(25)27-3/h4-8,13,17,20,23H,9-12H2,1-3H3

InChI Key

VAMJZLUOKJRHOW-UHFFFAOYSA-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 rhynchophylla	LOTUS Database	35616633
Uncaria sinensis	LOTUS Database	35616633

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
Quinolizine
Indole
Indole or derivatives
Aralkylamine
Piperidine
Benzenoid
Heteroaromatic compound
Pyrrole
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Carbonyl group
Organic nitrogen 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

External Links

HMDB ID

HMDB0252664

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

72381529

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Geissoschizine methyl ether

METLIN ID

Not Available

PubChem Compound

73810807

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kushida H, Matsumoto T, Ikarashi Y: Properties, Pharmacology, and Pharmacokinetics of Active Indole and Oxindole Alkaloids in Uncaria Hook. Front Pharmacol. 2021 Jul 14;12:688670. doi: 10.3389/fphar.2021.688670. eCollection 2021. [PubMed:34335255 ]
Kushida H, Matsumoto T, Ikarashi Y, Nishimura H, Yamamoto M: Gender differences in plasma pharmacokinetics and hepatic metabolism of geissoschizine methyl ether from Uncaria hook in rats. J Ethnopharmacol. 2021 Jan 10;264:113354. doi: 10.1016/j.jep.2020.113354. Epub 2020 Sep 6. [PubMed:32898626 ]
Matsumoto T, Ikarashi Y, Takiyama M, Watanabe J, Setou M: Brain distribution of geissoschizine methyl ether in rats using mass spectrometry imaging analysis. Sci Rep. 2020 Apr 29;10(1):7293. doi: 10.1038/s41598-020-63474-x. [PubMed:32350314 ]
Sun J, He F, Gao Y, Zhou Y, Zhang H, Huang M, Bi H: Lipidomics-based study on the neuroprotective effect of geissoschizine methyl ether against oxidative stress-induced cytotoxicity. J Ethnopharmacol. 2020 May 10;253:112636. doi: 10.1016/j.jep.2020.112636. Epub 2020 Jan 28. [PubMed:32004630 ]
Xie ZQ, Tian XT, Zheng YM, Zhan L, Chen XQ, Xin XM, Huang CG, Gao ZB: Antiepileptic geissoschizine methyl ether is an inhibitor of multiple neuronal channels. Acta Pharmacol Sin. 2020 May;41(5):629-637. doi: 10.1038/s41401-019-0327-4. Epub 2020 Jan 7. [PubMed:31911638 ]

Showing NP-Card for Geissoschizine methyl ether (NP0137253)

MOL for NP0137253 (Geissoschizine methyl ether)

3D MOL for NP0137253 (Geissoschizine methyl ether)

3D SDF for NP0137253 (Geissoschizine methyl ether)

3D-SDF for NP0137253 (Geissoschizine methyl ether)

PDB for NP0137253 (Geissoschizine methyl ether)

3D PDB for NP0137253 (Geissoschizine methyl ether)

SMILES for NP0137253 (Geissoschizine methyl ether)

INCHI for NP0137253 (Geissoschizine methyl ether)

Structure for NP0137253 (Geissoschizine methyl ether)

3D Structure for NP0137253 (Geissoschizine methyl ether)