NP-MRD: Showing NP-Card for methyl (2e)-2-[(2s,12br)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate (NP0277210)

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Record Information

Version

2.0

Created at

2022-09-09 01:44:36 UTC

Updated at

2022-09-09 01:44:36 UTC

NP-MRD ID

NP0277210

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Mitraciliatin 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,12br)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate is found in Mitragyna speciosa. Based on a literature review very few articles have been published on Mitraciliatin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092203442D          

 29 32  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  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
    6.2270   -4.2887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9210   -4.7347    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  1  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
  2  3  1  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  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
  8 18  1  0  0  0  0
 11 18  1  0  0  0  0
 19  9  1  6  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
   -1.2524   -3.3127   -0.4997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1235   -1.8097   -0.5895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6509   -1.1549    0.6589 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7613   -1.6612    1.7994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5132   -1.1064    1.6536 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6453   -1.9187    1.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8093   -1.3133    0.7950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4874   -0.1547   -0.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4202    0.6571    0.3387 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3334    1.6387   -0.5659 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2894    1.5050   -1.5109 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6339    2.2313   -2.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6984    1.8245   -3.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4282    0.6873   -3.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0839   -0.0315   -1.9709 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8120   -1.1639   -1.6376 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8975   -1.6343   -2.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0232    0.3808   -1.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6798    0.2819    1.5456 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7132    0.9265    1.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6152    0.3408    0.5454 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9788    0.8842    0.6542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3184    1.7713    1.5618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4733    2.2930    2.4961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6793    3.5897    3.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0512    0.4449   -0.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7992   -0.3840   -1.1443 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3152    0.9620   -0.1558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3913    0.5843   -1.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8592   -3.5485    0.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2777   -3.7837   -0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8030   -3.7079   -1.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4454   -1.3981   -1.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101   -1.6353   -0.5974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6982   -1.4705    0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6841   -2.7561    1.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3031   -1.3321    2.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0112   -2.2341    2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3698   -2.8698    0.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2422   -2.0901    0.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6675   -1.0993    1.4853 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6292    2.4112   -0.5584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0347    3.1026   -2.8549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9421    2.4059   -4.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2476    0.4141   -3.7418 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7630   -1.5619   -3.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8157   -1.0390   -2.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0746   -2.7120   -2.1244 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2314    0.7376    2.4173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515    0.6922    2.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514    1.9789    1.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2050    0.5971   -0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3754    2.1298    1.5760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6494    4.3723    2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9648    3.8122    3.8421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028    3.6949    3.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3350    0.7295   -0.4660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2486   -0.4675   -1.3630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4164    1.2695   -1.8904 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
 16 17  1  0
 15 18  2  0
  9 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 22 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  1  0
 21  3  1  0
 19  5  1  0
 18  8  1  0
 18 11  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  1
  4 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
 10 42  1  0
 12 43  1  0
 13 44  1  0
 14 45  1  0
 17 46  1  0
 17 47  1  0
 17 48  1  0
 19 49  1  1
 20 50  1  0
 20 51  1  0
 21 52  1  6
 23 53  1  0
 25 54  1  0
 25 55  1  0
 25 56  1  0
 29 57  1  0
 29 58  1  0
 29 59  1  0
M  END


  Mrv1652309092203442D          

 29 32  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  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
    6.2270   -4.2887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9210   -4.7347    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  1  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
  2  3  1  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  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  2  0  0  0  0
  8 18  1  0  0  0  0
 11 18  1  0  0  0  0
 19  9  1  6  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0277210

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1CN2CCC3=C(NC4=CC=CC(OC)=C34)[C@H]2C[C@@H]1\C(=C/OC)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14?,16-,19+/m0/s1

> <INCHI_KEY>
LELBFTMXCIIKKX-RGVOBYJXSA-N

> <FORMULA>
C23H30N2O4

> <MOLECULAR_WEIGHT>
398.503

> <EXACT_MASS>
398.220557454

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.526080969450454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.299593586666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.67027620485117

> <JCHEM_PKA_STRONGEST_BASIC>
7.042108351851677

> <JCHEM_POLAR_SURFACE_AREA>
63.790000000000006

> <JCHEM_REFRACTIVITY>
112.91319999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E)-2-[(2S,12bR)-3-ethyl-8-methoxy-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                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-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      12.919  -8.838   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.401  -5.635   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.533  -4.841   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.688  -3.554   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.151  -3.642   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.306  -2.354   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.768  -2.442   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.076  -3.818   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.462  -3.906   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.998  -0.979   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.153   0.309   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.536  -0.891   0.000  0.00  0.00           O+0
HETATM   29  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   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15    8   11                                                  
CONECT   19    9    5   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    3   22                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   22   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₀N₂O₄

Average Mass

398.5030 Da

Monoisotopic Mass

398.22056 Da

IUPAC Name

methyl (2E)-2-[(2S,12bR)-3-ethyl-8-methoxy-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,12bR)-3-ethyl-8-methoxy-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

CCC1CN2CCC3=C(NC4=CC=CC(OC)=C34)[C@H]2C[C@@H]1\C(=C/OC)C(=O)OC

InChI Identifier

InChI=1S/C23H30N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h6-8,13-14,16,19,24H,5,9-12H2,1-4H3/b17-13+/t14?,16-,19+/m0/s1

InChI Key

LELBFTMXCIIKKX-RGVOBYJXSA-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
Mitragyna speciosa	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
Anisole
Phenol ether
Alkyl aryl ether
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Pyrrole
Enoate ester
Methyl ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Amine
Hydrocarbon derivative
Organooxygen compound
Organic oxide
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	3.3	ChemAxon
pKa (Strongest Acidic)	16.67	ChemAxon
pKa (Strongest Basic)	7.04	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.79 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.91 m³·mol⁻¹	ChemAxon
Polarizability	45.53 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

68027457

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101281070

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2e)-2-[(2s,12br)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate (NP0277210)

MOL for NP0277210 (methyl (2e)-2-[(2s,12br)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D MOL for NP0277210 (methyl (2e)-2-[(2s,12br)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D SDF for NP0277210 (methyl (2e)-2-[(2s,12br)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D-SDF for NP0277210 (methyl (2e)-2-[(2s,12br)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

PDB for NP0277210 (methyl (2e)-2-[(2s,12br)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D PDB for NP0277210 (methyl (2e)-2-[(2s,12br)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

SMILES for NP0277210 (methyl (2e)-2-[(2s,12br)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

INCHI for NP0277210 (methyl (2e)-2-[(2s,12br)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

Structure for NP0277210 (methyl (2e)-2-[(2s,12br)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)

3D Structure for NP0277210 (methyl (2e)-2-[(2s,12br)-3-ethyl-8-methoxy-1h,2h,3h,4h,6h,7h,12h,12bh-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate)