NP-MRD: Showing NP-Card for Mitragynine (NP0050889)

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Record Information

Version

2.0

Created at

2022-04-27 22:21:06 UTC

Updated at

2025-01-30 20:45:10 UTC

NP-MRD ID

NP0050889

Natural Product DOI

https://doi.org/10.57994/0723

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Mitragynine

Description

Mitragynine, also known as SK and F-12711 or kratom alkaloids, 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. Mitragynine is found in Mitragyna speciosa. Mitragynine was first documented in 2020 (PMID: 32597657). Mitragynine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 06301311542D          

 30 33  0  0  0  0            999 V2000
   -1.3038   -0.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2091    0.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9592   -1.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565    1.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3828    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0376   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6198   -0.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0855    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0145    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    0.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8144   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    1.1022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1908    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.4596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3043   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8779    1.1504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671   -0.2772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725    3.2186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3855    1.0079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2651   -1.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    2.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9091    1.1965    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 14  5  1  1  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  2  0  0  0  0
 16 17  1  1  0  0  0
 18  7  1  0  0  0  0
 19 11  1  0  0  0  0
 20  8  2  0  0  0  0
 21 15  1  0  0  0  0
 21 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22 15  2  0  0  0  0
 22 19  1  0  0  0  0
 23 17  1  0  0  0  0
 24 18  1  0  0  0  0
 24 22  1  0  0  0  0
 25 10  1  0  0  0  0
 25 12  1  0  0  0  0
 25 19  1  0  0  0  0
 26 23  2  0  0  0  0
 27  2  1  0  0  0  0
 27 13  1  0  0  0  0
 28  3  1  0  0  0  0
 28 20  1  0  0  0  0
 29  4  1  0  0  0  0
 29 23  1  0  0  0  0
 19 30  1  6  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
   -4.3580   -1.2726    1.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8975   -1.0353    1.9613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9839   -1.3061    0.8351 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5552   -1.1195    1.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4073   -1.3541    0.3387 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6587   -1.6743    0.9060 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243   -1.4511   -0.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7575   -0.0016   -0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5314    0.5171   -0.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7521    1.8157   -0.9896 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0541    2.1273   -0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8068    3.2719   -1.0300 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1809    3.2382   -0.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8194    2.0597   -0.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0655    0.9205   -0.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6263   -0.2771    0.0957 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9765   -0.5083    0.3543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7089    0.9776   -0.4939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3508   -0.3717   -0.6806 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9350    0.4386   -0.5250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0797   -0.5809   -0.4343 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3386    0.0252   -0.8435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9340   -0.4477   -1.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3499   -1.4722   -2.6689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6889   -2.8334   -2.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0162    1.1506   -0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1064    1.6227   -0.6729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823    1.7989    0.9377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2443    2.8770    1.5418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5139   -1.5432    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7765   -2.1238    2.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9952   -0.3884    1.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343   -1.8408    2.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6895   -0.1086    2.5456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0840   -2.4458    0.6497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056   -0.0976    1.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795   -1.8459    2.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7109   -2.7641    1.1982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8922   -1.1253    1.8630 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7523   -2.0863   -0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7458   -1.6899    0.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9801    2.4671   -1.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3101    4.1860   -1.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7699    4.1393   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8869    2.0235   -0.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2471   -1.5605    0.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1838   -0.4619    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6688    0.1397   -0.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2740   -0.9266   -1.6657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9110    1.1526    0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1058    1.0086   -1.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7728   -1.3278   -1.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8573   -0.0340   -2.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7745   -2.9280   -2.7170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0834   -3.4502   -3.1605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5352   -3.1764   -1.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3255    2.7967    2.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2860    3.0119    1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7422    3.8649    1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
 20 21  1  0
 21  3  1  0
  3  2  1  0
  2  1  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 18  2  0
 18 15  1  0
 15 16  1  0
 16 17  1  0
 15 14  2  0
 14 13  1  0
 13 12  2  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
  5 19  1  0
 18  8  1  0
  9 19  1  0
 12 11  1  0
 19 49  1  6
 20 50  1  0
 20 51  1  0
 21 52  1  6
  3 35  1  6
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  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
 17 46  1  0
 17 47  1  0
 17 48  1  0
 14 45  1  0
 13 44  1  0
 12 43  1  0
 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


  Mrv0541 06301311542D          

 30 33  0  0  0  0            999 V2000
   -1.3038   -0.4187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2091    0.9608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9592   -1.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4565    1.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    0.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3828    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0376   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6198   -0.9670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0855    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0145    1.7448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    0.3654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8144   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    1.1022    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1908    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.4596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3043   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1802    2.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8779    1.1504    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671   -0.2772    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2725    3.2186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3855    1.0079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2651   -1.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0038    2.5760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9091    1.1965    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  7  6  2  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 14  5  1  1  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  2  0  0  0  0
 16 17  1  1  0  0  0
 18  7  1  0  0  0  0
 19 11  1  0  0  0  0
 20  8  2  0  0  0  0
 21 15  1  0  0  0  0
 21 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22 15  2  0  0  0  0
 22 19  1  0  0  0  0
 23 17  1  0  0  0  0
 24 18  1  0  0  0  0
 24 22  1  0  0  0  0
 25 10  1  0  0  0  0
 25 12  1  0  0  0  0
 25 19  1  0  0  0  0
 26 23  2  0  0  0  0
 27  2  1  0  0  0  0
 27 13  1  0  0  0  0
 28  3  1  0  0  0  0
 28 20  1  0  0  0  0
 29  4  1  0  0  0  0
 29 23  1  0  0  0  0
 19 30  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0050889

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@H]([C@H](CC)CN1CCC1=C2NC2=C1C(OC)=CC=C2)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+/m1/s1

> <INCHI_KEY>
LELBFTMXCIIKKX-QVRQZEMUSA-N

> <FORMULA>
C23H30N2O4

> <MOLECULAR_WEIGHT>
398.4953

> <EXACT_MASS>
398.220557458

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
43.29206734937068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
3.299593586666666

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.670276204945857

> <JCHEM_PKA_STRONGEST_BASIC>
7.3267983517564

> <JCHEM_POLAR_SURFACE_AREA>
63.790000000000006

> <JCHEM_REFRACTIVITY>
112.91319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mitragynine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-13         0                                  
HETATM    1  C   UNK     0      -2.434  -0.782   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.124   1.793   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.257  -3.139   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.719   3.521   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.741   0.594   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.477   1.476   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.181   2.308   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.404  -0.063   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.561  -1.717   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.024  -1.805   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.026   2.146   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.641  -0.606   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.894   3.257   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.204   0.682   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.254  -0.341   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.489   2.057   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.356   3.345   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.812   1.603   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.871   0.858   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.035  -0.768   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.739   0.064   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.409   0.946   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.336   4.720   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       5.372   2.147   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       2.179  -0.517   0.000  0.00  0.00           N+0
HETATM   26  O   UNK     0      -0.509   6.008   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.586   1.881   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       7.962  -2.306   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.874   4.809   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0       3.564   2.233   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2   27                                                            
CONECT    3   28                                                            
CONECT    4   29                                                            
CONECT    5    1   14                                                       
CONECT    6    7    8                                                       
CONECT    7    6   18                                                       
CONECT    8    6   20                                                       
CONECT    9   10   15                                                       
CONECT   10    9   25                                                       
CONECT   11   16   19                                                       
CONECT   12   14   25                                                       
CONECT   13   17   27                                                       
CONECT   14    5   12   16                                                  
CONECT   15    9   21   22                                                  
CONECT   16   11   14   17                                                  
CONECT   17   13   16   23                                                  
CONECT   18    7   21   24                                                  
CONECT   19   11   22   25   30                                             
CONECT   20    8   21   28                                                  
CONECT   21   15   18   20                                                  
CONECT   22   15   19   24                                                  
CONECT   23   17   26   29                                                  
CONECT   24   18   22                                                       
CONECT   25   10   12   19                                                  
CONECT   26   23                                                            
CONECT   27    2   13                                                       
CONECT   28    3   20                                                       
CONECT   29    4   23                                                       
CONECT   30   19                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Mitragynine ethanedisulfonate	HMDB
SK And F-12711	HMDB
Mitragynine monohydrochloride	HMDB
SK And F 12711	HMDB
Mitragynine, (3beta,16E,20beta)-isomer	HMDB
Mitragynine, (16E)-isomer	HMDB
Mitragynine, (3beta,16E)-isomer	HMDB
16,17-Didehydro-9,17-dimethoxy-17,18-seco-20-alpha-yohimban-16-carboxylic acid methyl ester	MeSH
Kratom alkaloids	MeSH
Methyl (2E)-2-[(2S,4S,5S)-5-ethyl-12-methoxy-7,17-diazatetracyclo[8.7.0.0,.0,]heptadeca-1(10),11(16),12,14-tetraen-4-yl]-3-methoxyprop-2-enoic acid	Generator

Chemical Formula

C₂₃H₃₀N₂O₄

Average Mass

398.4953 Da

Monoisotopic Mass

398.22056 Da

IUPAC Name

methyl (2E)-2-[(2S,3S,12bS)-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

mitragynine

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@H]([C@H](CC)CN1CCC1=C2NC2=C1C(OC)=CC=C2)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+/m1/s1

InChI Key

LELBFTMXCIIKKX-QVRQZEMUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	nicholas_oberlies@uncg.edu	UNCG Oberlies Lab	Zijian Rong	2025-01-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	nicholas_oberlies@uncg.edu	UNCG Oberlies Lab	Zijian Rong	2025-01-30	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCL3, experimental)	z_rong@uncg.edu	University of North Carolina at Greensboro	Zijian Rong	2024-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCL3, experimental)	z_rong@uncg.edu	University of North Carolina at Greensboro	Zijian Rong	2024-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	n_oberli@uncg.edu	Not Available	Not Available	2023-07-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	n_oberli@uncg.edu	Not Available	Not Available	2023-07-13	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	n_oberli@uncg.edu	Not Available	Not Available	2023-07-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	n_oberli@uncg.edu	Not Available	Not Available	2023-07-12	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 M. speciosa		Not Available
Mitragyna M. speciosa		Not Available
Mitragyna speciosa		Not Available
Mitragyna speciosa	Plant	KNApSAcK

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monoterpenoid indole alkaloid (CHEBI:6956 )

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	4	ALOGPS
logP	3.3	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	16.67	ChemAxon
pKa (Strongest Basic)	7.33	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	43.29 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