NP-MRD: Showing NP-Card for methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate (NP0248956)

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Record Information

Version

2.0

Created at

2022-09-07 11:23:14 UTC

Updated at

2022-09-07 11:23:15 UTC

NP-MRD ID

NP0248956

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

Description

Gambirine 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. methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate was first documented in 2006 (PMID: 17039876). Based on a literature review very few articles have been published on Gambirine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072213232D          

 28 31  0  0  1  0            999 V2000
    0.6580   -3.4718    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  1  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
    6.2270   -4.2887    0.0000 O   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
    0.5764   -2.0451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -2.0923    0.0000 C   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
    3.4183   -1.1668    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  6  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  1  0  0  0  0
 15 17  2  0  0  0  0
  8 17  1  0  0  0  0
 11 17  1  0  0  0  0
 18  9  1  1  0  0  0
  5 18  1  0  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  1  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
    3.0400   -3.0325    0.7957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7596   -2.4728   -0.5838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5897   -1.5215   -0.5757 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4783   -2.3982   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7578   -1.7502    0.0012 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4227   -1.6414   -1.2388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6805   -0.8491   -1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9178    0.0121   -0.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9641    0.1622    0.8797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4857    1.0115    1.8020 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7185    1.3828    1.4252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6559    2.2226    2.0095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8663    2.4352    1.4013 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1899    1.8376    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2464    0.9885   -0.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6313    0.4225   -1.5635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0397    0.7739    0.2240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6774   -0.5467    0.7682 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3288    0.4204    0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905   -0.2325    0.1048 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7755    0.6919   -0.2251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4569    1.8708   -0.8020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1920    2.2279   -1.0843 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7890    3.5988   -1.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1837    0.4932    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0046    1.4111   -0.2849 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7788   -0.5785    0.6484 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1683   -0.6948    0.8875 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4644   -3.9612    0.9838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -2.2800    1.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1091   -3.3064    0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6238   -2.1683   -1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3616   -3.3762   -1.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3564   -1.3660   -1.6910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7547   -2.6919    1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4443   -3.2810   -0.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7136   -1.1450   -1.9651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5661   -2.6645   -1.6561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5159   -1.6115   -1.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8031   -0.2793   -2.2165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9643    1.2956    2.6509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4127    2.7079    2.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5718    3.0908    1.8781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1635    2.0103   -0.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1165   -0.1849   -2.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3078   -0.7833    1.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3221    1.2931    0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1183    0.5524   -0.8830 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8693   -0.4785    1.2127 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2448    2.5831   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2754    3.7155   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3569    4.1626   -1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0580    4.0897   -0.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7770   -0.2227    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4919   -1.7604    0.9274 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4713   -0.1847    1.8268 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  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  1  0
 15 17  2  0
  9 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
 20  3  1  0
 18  5  1  0
 17  8  1  0
 17 11  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
 10 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 16 45  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
M  END


  Mrv1652309072213232D          

 28 31  0  0  1  0            999 V2000
    0.6580   -3.4718    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  1  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
    6.2270   -4.2887    0.0000 O   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
    0.5764   -2.0451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2473   -2.0923    0.0000 C   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
    3.4183   -1.1668    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  6  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  1  0  0  0  0
 15 17  2  0  0  0  0
  8 17  1  0  0  0  0
 11 17  1  0  0  0  0
 18  9  1  1  0  0  0
  5 18  1  0  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  1  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>
NP0248956

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1CN2CCC3=C(NC4=CC=CC(O)=C34)[C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H28N2O4/c1-4-13-11-24-9-8-14-20-17(6-5-7-19(20)25)23-21(14)18(24)10-15(13)16(12-27-2)22(26)28-3/h5-7,12-13,15,18,23,25H,4,8-11H2,1-3H3/b16-12+/t13-,15-,18-/m0/s1

> <INCHI_KEY>
IIRZCWUQUBSIPF-ZZTFNPIZSA-N

> <FORMULA>
C22H28N2O4

> <MOLECULAR_WEIGHT>
384.476

> <EXACT_MASS>
384.20490739

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.031911788474346

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E)-2-[(2S,3R,12bS)-3-ethyl-8-hydroxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

> <JCHEM_LOGP>
3.1536995306666675

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.10148017986609

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.17921883242028

> <JCHEM_PKA_STRONGEST_BASIC>
7.044880410696927

> <JCHEM_POLAR_SURFACE_AREA>
74.79

> <JCHEM_REFRACTIVITY>
108.43089999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-2-[(2S,3R,12bS)-3-ethyl-8-hydroxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       1.228  -6.481   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  O   UNK     0      11.624  -8.006   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      10.401  -5.635   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.533  -4.841   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.688  -3.554   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.151  -3.642   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.306  -2.354   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.768  -2.442   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.076  -3.818   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.462  -3.906   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.998  -0.979   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.153   0.309   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.536  -0.891   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.381  -2.178   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                                                  
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8   11                                                  
CONECT   18    9    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

Not Available

Chemical Formula

C₂₂H₂₈N₂O₄

Average Mass

384.4760 Da

Monoisotopic Mass

384.20491 Da

IUPAC Name

methyl (2E)-2-[(2S,3R,12bS)-3-ethyl-8-hydroxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

Traditional Name

methyl (2E)-2-[(2S,3R,12bS)-3-ethyl-8-hydroxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC[C@H]1CN2CCC3=C(NC4=CC=CC(O)=C34)[C@@H]2C[C@@H]1\C(=C/OC)C(=O)OC

InChI Identifier

InChI=1S/C22H28N2O4/c1-4-13-11-24-9-8-14-20-17(6-5-7-19(20)25)23-21(14)18(24)10-15(13)16(12-27-2)22(26)28-3/h5-7,12-13,15,18,23,25H,4,8-11H2,1-3H3/b16-12+/t13-,15-,18-/m0/s1

InChI Key

IIRZCWUQUBSIPF-ZZTFNPIZSA-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

Not Available

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
Hydroxyindole
Quinolizine
3-alkylindole
Indole
Indole or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Benzenoid
Piperidine
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Heteroaromatic compound
Methyl ester
Vinylogous ester
Pyrrole
Tertiary aliphatic amine
Carboxylic acid ester
Amino acid or derivatives
Tertiary amine
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carboxylic acid derivative
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
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	3.15	ChemAxon
pKa (Strongest Acidic)	9.18	ChemAxon
pKa (Strongest Basic)	7.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.79 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	108.43 m³·mol⁻¹	ChemAxon
Polarizability	43.03 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

C00050933

Chemspider ID

2300830

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3036945

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kang WY, Zhang BR, Xu QT, Li L, Hao XJ: [Study on the chemical constituents of Mitragyna rotundifolia]. Zhong Yao Cai. 2006 Jun;29(6):557-60. [PubMed:17039876 ]
LOTUS database [Link]

Showing NP-Card for methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate (NP0248956)

MOL for NP0248956 (methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D MOL for NP0248956 (methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D SDF for NP0248956 (methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D-SDF for NP0248956 (methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

PDB for NP0248956 (methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D PDB for NP0248956 (methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

SMILES for NP0248956 (methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

INCHI for NP0248956 (methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

Structure for NP0248956 (methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D Structure for NP0248956 (methyl (2e)-2-[(2s,3r,12bs)-3-ethyl-8-hydroxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)