NP-MRD: Showing NP-Card for 3-Isopaynantheine (NP0067434)

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Record Information

Version

2.0

Created at

2022-04-28 12:17:33 UTC

Updated at

2024-09-12 20:39:11 UTC

NP-MRD ID

NP0067434

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Isopaynantheine

Description

3-Isopaynantheine 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. 3-Isopaynantheine is found in Mitragyna hirsuta, Mitragyna speciosa and Mitragyna speciosa Korth.. 3-Isopaynantheine was first documented in 2013 (PMID: 24169379). Based on a literature review very few articles have been published on 3-Isopaynantheine (PMID: 24659356).

Structure

MOL SDF PDB SMILES InChI

NP0067434
  Mrv2104 05272323113D          

 57 60  0  0  0  0            999 V2000
   -3.9933    2.6670   -0.6690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597    2.0053   -0.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6892    0.5073   -0.5834 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7794    0.1409   -1.7787 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3319    0.2565   -1.5838 N   0  0  1  0  0  0  0  0  0  0  0  0
    0.1959    1.6242   -1.7736 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7413    1.6572   -1.8850 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3471    0.8109   -0.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5911   -0.1248   -0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121   -0.7644    0.7412 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902   -0.2515    0.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8462   -0.6019    1.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0273    0.0760    1.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0494    1.0733    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8801    1.4363   -0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8726    2.4051   -1.5842 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5478    3.5993   -1.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797    0.7463   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291   -0.3983   -0.3426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6814    0.0259    0.8968 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2050   -0.1753    0.7303 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6919   -1.6161    0.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9700   -2.7225    1.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5238   -3.9668    1.2478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5952   -5.0209    1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1583   -1.8165    0.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7152   -2.3218   -0.2151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7496   -1.2959    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1712   -1.4134    1.8431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0624    3.7387   -0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8735    2.1633   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0211    2.5713   -0.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6850    0.1225   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0865    0.7011   -2.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9792   -0.9092   -2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0986    2.2735   -0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2144    2.0661   -2.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0485    1.2719   -2.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    2.6942   -1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1402   -1.5102    1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8360   -1.3806    2.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9464   -0.1854    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9944    1.5557   -0.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1781    4.4106   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6244    3.5019   -1.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3477    3.8710   -0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0264   -1.4794   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3267   -0.5120    1.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4869    1.0849    1.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6686    0.3507    1.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8976   -2.7139    1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1396   -5.9687    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1396   -4.9241    0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8234   -5.0348    1.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4649   -2.4667    1.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5592   -0.9042    2.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5966   -0.9296    0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  3  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
 21  3  1  0  0  0  0
 19  5  1  0  0  0  0
 18  8  1  0  0  0  0
 18 11  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  2 32  1  0  0  0  0
  3 33  1  6  0  0  0
  4 34  1  0  0  0  0
  4 35  1  0  0  0  0
  6 36  1  0  0  0  0
  6 37  1  0  0  0  0
  7 38  1  0  0  0  0
  7 39  1  0  0  0  0
 10 40  1  0  0  0  0
 12 41  1  0  0  0  0
 13 42  1  0  0  0  0
 14 43  1  0  0  0  0
 17 44  1  0  0  0  0
 17 45  1  0  0  0  0
 17 46  1  0  0  0  0
 19 47  1  6  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
 21 50  1  1  0  0  0
 23 51  1  0  0  0  0
 25 52  1  0  0  0  0
 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
 29 55  1  0  0  0  0
 29 56  1  0  0  0  0
 29 57  1  0  0  0  0
M  END

NP0067434
  Mrv2104 05272323113D          

 57 60  0  0  0  0            999 V2000
   -3.9933    2.6670   -0.6690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8597    2.0053   -0.3999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6892    0.5073   -0.5834 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7794    0.1409   -1.7787 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3319    0.2565   -1.5838 N   0  0  1  0  0  0  0  0  0  0  0  0
    0.1959    1.6242   -1.7736 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7413    1.6572   -1.8850 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3471    0.8109   -0.8189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5911   -0.1248   -0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4121   -0.7644    0.7412 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6902   -0.2515    0.6564 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8462   -0.6019    1.3640 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0273    0.0760    1.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0494    1.0733    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8801    1.4363   -0.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8726    2.4051   -1.5842 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5478    3.5993   -1.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797    0.7463   -0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1291   -0.3983   -0.3426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6814    0.0259    0.8968 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2050   -0.1753    0.7303 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6919   -1.6161    0.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9700   -2.7225    1.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5238   -3.9668    1.2478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5952   -5.0209    1.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1583   -1.8165    0.7464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7152   -2.3218   -0.2151 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7496   -1.2959    1.8494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1712   -1.4134    1.8431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0624    3.7387   -0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8735    2.1633   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0211    2.5713   -0.0049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6850    0.1225   -0.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0865    0.7011   -2.6718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9792   -0.9092   -2.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0986    2.2735   -0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2144    2.0661   -2.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0485    1.2719   -2.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0871    2.6942   -1.8002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1402   -1.5102    1.3663 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8360   -1.3806    2.1197 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9464   -0.1854    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9944    1.5557   -0.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1781    4.4106   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6244    3.5019   -1.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3477    3.8710   -0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0264   -1.4794   -0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3267   -0.5120    1.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4869    1.0849    1.1175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6686    0.3507    1.5788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8976   -2.7139    1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1396   -5.9687    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1396   -4.9241    0.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8234   -5.0348    1.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4649   -2.4667    1.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5592   -0.9042    2.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5966   -0.9296    0.9580 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  3  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
 21  3  1  0  0  0  0
 19  5  1  0  0  0  0
 18  8  1  0  0  0  0
 18 11  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  2 32  1  0  0  0  0
  3 33  1  6  0  0  0
  4 34  1  0  0  0  0
  4 35  1  0  0  0  0
  6 36  1  0  0  0  0
  6 37  1  0  0  0  0
  7 38  1  0  0  0  0
  7 39  1  0  0  0  0
 10 40  1  0  0  0  0
 12 41  1  0  0  0  0
 13 42  1  0  0  0  0
 14 43  1  0  0  0  0
 17 44  1  0  0  0  0
 17 45  1  0  0  0  0
 17 46  1  0  0  0  0
 19 47  1  6  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
 21 50  1  1  0  0  0
 23 51  1  0  0  0  0
 25 52  1  0  0  0  0
 25 53  1  0  0  0  0
 25 54  1  0  0  0  0
 29 55  1  0  0  0  0
 29 56  1  0  0  0  0
 29 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0067434

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C([H])[C@@]1([H])C([H])([H])N2C([H])([H])C([H])([H])C3=C(N([H])C4=C([H])C([H])=C([H])C(OC([H])([H])[H])=C34)[C@@]2([H])C([H])([H])[C@]1([H])C(=C([H])OC([H])([H])[H])C(=O)OC([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1/C23H28N2O4/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/h5-8,13-14,16,19,24H,1,9-12H2,2-4H3/b17-13-/t14-,16-,19+/s2

> <INCHI_KEY>
JGZKIGWXPPFMRG-JBUZHXCTNA-N

> <FORMULA>
C23H28N2O4

> <MOLECULAR_WEIGHT>
396.487

> <EXACT_MASS>
396.20490739

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
44.80669278260098

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
2.995605600333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.670265610387272

> <JCHEM_PKA_STRONGEST_BASIC>
6.898711484113814

> <JCHEM_POLAR_SURFACE_AREA>
63.790000000000006

> <JCHEM_REFRACTIVITY>
112.95729999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[(2S,3R,12bR)-3-ethenyl-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                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: NP0067434                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0      -3.993   2.667  -0.669  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.860   2.005  -0.400  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.689   0.507  -0.583  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.779   0.141  -1.779  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.332   0.257  -1.584  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.196   1.624  -1.774  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.741   1.657  -1.885  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.347   0.811  -0.819  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.591  -0.125  -0.143  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.412  -0.764   0.741  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.690  -0.252   0.656  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.846  -0.602   1.364  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.027   0.076   1.052  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.049   1.073   0.077  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.880   1.436  -0.608  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.873   2.405  -1.584  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.548   3.599  -1.201  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.680   0.746  -0.324  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.129  -0.398  -0.343  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.681   0.026   0.897  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.205  -0.175   0.730  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.692  -1.616   0.852  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.970  -2.723   1.092  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.524  -3.967   1.248  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.595  -5.021   1.005  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.158  -1.817   0.746  0.00  0.00           C+0
HETATM   27  O   UNK     0      -4.715  -2.322  -0.215  0.00  0.00           O+0
HETATM   28  O   UNK     0      -4.750  -1.296   1.849  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.171  -1.413   1.843  0.00  0.00           C+0
HETATM   30  H   UNK     0      -4.062   3.739  -0.508  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.874   2.163  -1.057  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.021   2.571  -0.005  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.685   0.123  -0.840  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.087   0.701  -2.672  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.979  -0.909  -2.033  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.099   2.273  -0.944  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.214   2.066  -2.689  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.049   1.272  -2.865  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.087   2.694  -1.800  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.140  -1.510   1.366  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.836  -1.381   2.120  0.00  0.00           H+0
HETATM   42  H   UNK     0       6.946  -0.185   1.572  0.00  0.00           H+0
HETATM   43  H   UNK     0       6.994   1.556  -0.153  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.178   4.411  -1.836  0.00  0.00           H+0
HETATM   45  H   UNK     0       6.624   3.502  -1.376  0.00  0.00           H+0
HETATM   46  H   UNK     0       5.348   3.871  -0.157  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.026  -1.479  -0.495  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.327  -0.512   1.786  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.487   1.085   1.117  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.669   0.351   1.579  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.898  -2.714   1.229  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.140  -5.969   1.045  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.140  -4.924   0.014  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.823  -5.035   1.784  0.00  0.00           H+0
HETATM   55  H   UNK     0      -6.465  -2.467   1.889  0.00  0.00           H+0
HETATM   56  H   UNK     0      -6.559  -0.904   2.731  0.00  0.00           H+0
HETATM   57  H   UNK     0      -6.597  -0.930   0.958  0.00  0.00           H+0
CONECT    1    2   30   31                                                  
CONECT    2    1    3   32                                                  
CONECT    3    2    4   21   33                                             
CONECT    4    3    5   34   35                                             
CONECT    5    4    6   19                                                  
CONECT    6    5    7   36   37                                             
CONECT    7    6    8   38   39                                             
CONECT    8    7    9   18                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   40                                                  
CONECT   11   10   12   18                                                  
CONECT   12   11   13   41                                                  
CONECT   13   12   14   42                                                  
CONECT   14   13   15   43                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   44   45   46                                             
CONECT   18   15    8   11                                                  
CONECT   19    9   20    5   47                                             
CONECT   20   19   21   48   49                                             
CONECT   21   20   22    3   50                                             
CONECT   22   21   23   26                                                  
CONECT   23   22   24   51                                                  
CONECT   24   23   25                                                       
CONECT   25   24   52   53   54                                             
CONECT   26   22   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   55   56   57                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    2                                                            
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    4                                                            
CONECT   36    6                                                            
CONECT   37    6                                                            
CONECT   38    7                                                            
CONECT   39    7                                                            
CONECT   40   10                                                            
CONECT   41   12                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   17                                                            
CONECT   45   17                                                            
CONECT   46   17                                                            
CONECT   47   19                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   23                                                            
CONECT   52   25                                                            
CONECT   53   25                                                            
CONECT   54   25                                                            
CONECT   55   29                                                            
CONECT   56   29                                                            
CONECT   57   29                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₈N₂O₄

Average Mass

396.4870 Da

Monoisotopic Mass

396.20491 Da

IUPAC Name

methyl 2-[(2S,3R,12bR)-3-ethenyl-8-methoxy-1H,2H,3H,4H,6H,7H,12H,12bH-indolo[2,3-a]quinolizin-2-yl]-3-methoxyprop-2-enoate

Traditional Name

methyl 2-[(2S,3R,12bR)-3-ethenyl-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

[H]C([H])=C([H])[C@@]1([H])C([H])([H])N2C([H])([H])C([H])([H])C3=C(N([H])C4=C([H])C([H])=C([H])C(OC([H])([H])[H])=C34)[C@@]2([H])C([H])([H])[C@]1([H])C(=C([H])OC([H])([H])[H])C(=O)OC([H])([H])[H]

InChI Identifier

InChI=1/C23H28N2O4/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/h5-8,13-14,16,19,24H,1,9-12H2,2-4H3/b17-13-/t14-,16-,19+/s2

InChI Key

JGZKIGWXPPFMRG-JBUZHXCTNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mitragyna hirsuta	LOTUS Database	35616633
Mitragyna speciosa	LOTUS Database	35616633
Mitragyna speciosa Korth.	Plant	KNApSAcK

Chemical Taxonomy

Description

This compound 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
Pyridoindole
Beta-carboline
3-alkylindole
Quinolizine
Indole or derivatives
Indole
Anisole
Aralkylamine
Alkyl aryl ether
Benzenoid
Piperidine
Heteroaromatic compound
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	ChemAxon
pKa (Strongest Acidic)	16.67	ChemAxon
pKa (Strongest Basic)	6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.79 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	112.96 m³·mol⁻¹	ChemAxon
Polarizability	44.81 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cao XF, Wang JS, Wang XB, Luo J, Wang HY, Kong LY: Monoterpene indole alkaloids from the stem bark of Mitragyna diversifolia and their acetylcholine esterase inhibitory effects. Phytochemistry. 2013 Dec;96:389-96. doi: 10.1016/j.phytochem.2013.10.002. Epub 2013 Oct 26. [PubMed:24169379 ]
Wang M, Carrell EJ, Ali Z, Avula B, Avonto C, Parcher JF, Khan IA: Comparison of three chromatographic techniques for the detection of mitragynine and other indole and oxindole alkaloids in Mitragyna speciosa (kratom) plants. J Sep Sci. 2014 Jun;37(12):1411-8. doi: 10.1002/jssc.201301389. Epub 2014 Apr 25. [PubMed:24659356 ]

Showing NP-Card for 3-Isopaynantheine (NP0067434)

MOL for NP0067434 (3-Isopaynantheine)

3D MOL for NP0067434 (3-Isopaynantheine)

3D SDF for NP0067434 (3-Isopaynantheine)

3D-SDF for NP0067434 (3-Isopaynantheine)

PDB for NP0067434 (3-Isopaynantheine)

3D PDB for NP0067434 (3-Isopaynantheine)

SMILES for NP0067434 (3-Isopaynantheine)

INCHI for NP0067434 (3-Isopaynantheine)

Structure for NP0067434 (3-Isopaynantheine)

3D Structure for NP0067434 (3-Isopaynantheine)