NP-MRD: Showing NP-Card for methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate (NP0316253)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 15:19:29 UTC

Updated at

2022-09-11 15:19:29 UTC

NP-MRD ID

NP0316253

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate

Description

(19E)-geissoschizine 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 (19E)-geissoschizine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate is found in Alstonia scholaris and Alstonia angustiloba. methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate was first documented in 2018 (PMID: 29511102). Based on a literature review very few articles have been published on (19E)-geissoschizine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112217192D          

 26 29  0  0  1  0            999 V2000
    0.5764   -2.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -2.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053   -3.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -3.3303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -4.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236   -2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8397   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9995   -3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.5934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0473   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -1.9509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4947   -0.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.1655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657   -0.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3367    0.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  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  2  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8 16  1  0  0  0  0
 11 16  1  0  0  0  0
 17  9  1  1  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 20 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
M  END

     RDKit          3D

 50 53  0  0  0  0  0  0  0  0999 V2000
   -3.6906    2.6250   -0.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2431    2.7018   -0.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4013    1.8657    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1132    2.1209    0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8531    1.3287    0.9756 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1575    1.7564    1.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1395    0.6457    1.5553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9560   -0.4390    0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6605   -0.7762    0.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6636   -1.7608   -0.7043 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9398   -2.0458   -1.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -2.9240   -1.8814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9252   -3.0009   -1.9966 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6990   -2.1743   -1.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1396   -1.2713   -0.3374 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695   -1.2210   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6136   -0.0455    0.9931 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7714   -0.4302    0.5089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7101    0.6934    1.0265 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0275    0.1096    1.0745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6532    0.0025    2.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9065   -0.5655    2.3965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6824   -0.3959   -0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8165   -0.9183   -0.0050 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1258   -0.3413   -1.3798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7817   -0.8420   -2.5277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1423    2.3080    0.7632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0414    3.7219   -0.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1923    2.2042   -1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7699    3.5499   -0.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2399    3.1943    0.3020 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3713    1.9389   -0.9736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2206    2.4733    2.0823 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6318    2.3178    0.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0054    0.2565    2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1541    1.0274    1.4513 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8075   -2.2073   -1.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9391   -3.5817   -2.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4337   -3.6856   -2.6713 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7841   -2.1915   -1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7261   -0.6094    0.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6691   -0.3978    2.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7489   -0.4403   -0.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0170   -1.3954    0.9764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2873    0.8723    2.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1594    0.3822    3.1105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0899   -1.5468    2.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8717   -0.8884   -2.3420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4379   -1.8730   -2.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5990   -0.1272   -3.3491 H   0  0  0  0  0  0  0  0  0  0  0  0
 26 25  1  0
 25 23  1  0
 23 24  2  0
 23 20  1  0
 20 21  2  0
 21 22  1  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
  3 19  1  0
  9 17  1  0
 16 11  1  0
 16  8  1  0
 26 48  1  0
 26 49  1  0
 26 50  1  0
 21 46  1  0
 22 47  1  0
 19 45  1  1
 18 43  1  0
 18 44  1  0
 17 42  1  1
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
 10 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
  4 31  1  0
  4 32  1  0
  2 30  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END


  Mrv1652309112217192D          

 26 29  0  0  1  0            999 V2000
    0.5764   -2.0451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8527   -2.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3053   -3.3775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -3.3303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5816   -4.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053   -3.9729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7763   -3.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3236   -2.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8397   -1.9027    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6113   -2.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3446   -1.8165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387   -2.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9995   -3.0866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -3.4647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5721   -3.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000   -2.5934    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0473   -1.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2237   -1.9509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -1.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9474   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4947   -0.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420   -0.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894    0.1655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657   -0.4771    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3367    0.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  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  2  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  8 16  1  0  0  0  0
 11 16  1  0  0  0  0
 17  9  1  1  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 20 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
M  END
> <DATABASE_ID>
NP0316253

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(=C/O)\[C@H]1C[C@@H]2N(CCC3=C2NC2=CC=CC=C32)C\C1=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O3/c1-3-13-11-23-9-8-15-14-6-4-5-7-18(14)22-20(15)19(23)10-16(13)17(12-24)21(25)26-2/h3-7,12,16,19,22,24H,8-11H2,1-2H3/b13-3-,17-12-/t16-,19-/m0/s1

> <INCHI_KEY>
WKWHYFHGTWZCLM-KGZWXYIYSA-N

> <FORMULA>
C21H24N2O3

> <MOLECULAR_WEIGHT>
352.434

> <EXACT_MASS>
352.178692641

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.49207381705314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2Z)-2-[(2S,3E,12bS)-3-ethylidene-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate

> <JCHEM_LOGP>
3.0168117116666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.37438369705817

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.546355894119214

> <JCHEM_PKA_STRONGEST_BASIC>
6.337176858685023

> <JCHEM_POLAR_SURFACE_AREA>
65.56

> <JCHEM_REFRACTIVITY>
102.47179999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2Z)-2-[(2S,3E,12bS)-3-ethylidene-1H,2H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       1.076  -3.818   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.921  -5.105   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.458  -5.017   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.303  -6.305   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       5.841  -6.217   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.686  -7.504   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.223  -7.416   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.916  -6.041   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.071  -4.753   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       9.034  -3.552   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      10.475  -4.097   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.843  -3.391   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.139  -4.223   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.066  -5.762   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.697  -6.467   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.401  -5.635   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.533  -4.841   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.688  -3.554   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.151  -3.642   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.306  -2.354   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.768  -2.442   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.923  -1.155   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.998  -0.979   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.153   0.309   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.536  -0.891   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.228   0.485   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    8   11                                                  
CONECT   17    9    5   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18    3   20                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

View in JSmol

Synonyms

Value	Source
(+)-Geissoschizine	ChEBI
(16Z,19E)-17-Hydroxy-16-methoxycarbonyl-16,19-didehydro-corynane	ChEBI
19E-Geissoschizine	ChEBI
Geissoschizine	ChEBI

Chemical Formula

C₂₁H₂₄N₂O₃

Average Mass

352.4340 Da

Monoisotopic Mass

352.17869 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC(=O)C(=C/O)\[C@H]1C[C@@H]2N(CCC3=C2NC2=CC=CC=C32)C\C1=C\C

InChI Identifier

InChI=1S/C21H24N2O3/c1-3-13-11-23-9-8-15-14-6-4-5-7-18(14)22-20(15)19(23)10-16(13)17(12-24)21(25)26-2/h3-7,12,16,19,22,24H,8-11H2,1-2H3/b13-3-,17-12-/t16-,19-/m0/s1

InChI Key

WKWHYFHGTWZCLM-KGZWXYIYSA-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
Alstonia Alstonia scholaris	LOTUS Database	35616633
Alstonia angustiloba	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
Quinolizine
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Piperidine
Benzenoid
Heteroaromatic compound
Pyrrole
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Tertiary amine
Amino acid or derivatives
Tertiary aliphatic amine
Carboxylic acid ester
Azacycle
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Enol
Amine
Organopnictogen compound
Organic oxide
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00051968

Chemspider ID

9123384

KEGG Compound ID

Not Available

BioCyc ID

GEISSOSCHIZINE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10948159

PDB ID

Not Available

ChEBI ID

17037

Good Scents ID

Not Available

References

General References

Qu Y, Easson MEAM, Simionescu R, Hajicek J, Thamm AMK, Salim V, De Luca V: Solution of the multistep pathway for assembly of corynanthean, strychnos, iboga, and aspidosperma monoterpenoid indole alkaloids from 19E-geissoschizine. Proc Natl Acad Sci U S A. 2018 Mar 20;115(12):3180-3185. doi: 10.1073/pnas.1719979115. Epub 2018 Mar 6. [PubMed:29511102 ]
LOTUS database [Link]

Showing NP-Card for methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate (NP0316253)

MOL for NP0316253 (methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate)

3D MOL for NP0316253 (methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate)

3D SDF for NP0316253 (methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate)

3D-SDF for NP0316253 (methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate)

PDB for NP0316253 (methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate)

3D PDB for NP0316253 (methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate)

SMILES for NP0316253 (methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate)

INCHI for NP0316253 (methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate)

Structure for NP0316253 (methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate)

3D Structure for NP0316253 (methyl (2z)-2-[(2s,3e,12bs)-3-ethylidene-1h,2h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate)