NP-MRD: Showing NP-Card for methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate (NP0242849)

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Record Information

Version

2.0

Created at

2022-09-07 03:16:06 UTC

Updated at

2022-09-07 03:16:06 UTC

NP-MRD ID

NP0242849

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate

Description

Methyl 2-[(3R,6'S,7'R,8'aS)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate is found in Mitragyna rotundifolia and Mitragyna tubulosa. Based on a literature review very few articles have been published on methyl 2-[(3R,6'S,7'R,8'aS)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072205162D          

 30 33  0  0  1  0            999 V2000
    0.6034   -0.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4720   -0.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2494    0.3170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0779    1.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    1.6761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4756    2.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9605    2.0886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4455    2.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4840    3.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    2.5011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8432    1.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6716    0.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8870    0.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739    0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5532    0.0931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8401    0.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455    1.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4756    1.4211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6471    0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0340    0.0621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8842   -0.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486   -1.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501   -1.9522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6302   -2.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1718   -1.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316   -2.3474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819   -1.8800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2518   -2.6596    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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 12 19  1  0  0  0  0
  8 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20  5  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  4  0  0  0
 25 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 60 63  0  0  0  0  0  0  0  0999 V2000
   -2.8034    3.0865    2.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6576    2.2587    0.9789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6121    1.1362    1.1501 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3221    1.9433    1.4456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4607    1.9107    0.2572 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6092    2.7451    0.2512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7633    1.9226   -0.2810 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1077    0.6737   -0.7522 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6115    0.8424   -2.1336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7399    1.8498   -2.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1093   -0.0694   -2.8749 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9619   -0.9262   -2.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6845   -2.0215   -2.5482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4685   -2.7385   -1.6563 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4973   -2.3219   -0.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7714   -1.2256    0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8290   -0.8388    1.3827 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6122   -1.5335    2.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9837   -0.4955   -0.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292    0.5151    0.1640 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2010   -0.2462   -0.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5627    0.4319   -0.1633 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6471   -0.5192   -0.3627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5672   -0.8115    0.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7634   -0.3460    1.7812 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0600   -1.2568    2.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7409   -1.2240   -1.6905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9077   -0.9945   -2.5799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7536   -2.1313   -1.9309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9052   -2.8264   -3.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2768    2.6493    3.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4979    4.1484    2.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8994    3.1427    2.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1636    2.9155    0.1787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5825    1.9369    0.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8510    0.5195    2.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1956    1.3474    2.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5328    2.9296    1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8369    3.2352    1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226    3.5776   -0.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5401    1.7743    0.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2371    2.4170   -1.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2253    1.7896   -3.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552   -2.3487   -3.5955 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0301   -3.6006   -2.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1045   -2.8747    0.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4860   -1.0049    3.3033 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3314   -2.6114    2.3974 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6815   -1.4298    2.0112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1766    0.1205    1.1527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793   -1.2881   -0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0784   -0.2074   -1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6653    1.2346   -0.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3296   -1.5646    0.2014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0108   -1.7807    2.5404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1479   -0.7314    3.7839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2580   -2.0245    2.8130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5269   -2.2510   -4.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0050   -2.9700   -3.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4530   -3.8398   -3.1101 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 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  1  0
 23 27  1  0
 27 28  2  0
 27 29  1  0
 29 30  1  0
  8  9  1  6
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 22  3  1  0
 19 12  1  0
 20  5  1  0
 19  8  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  1
  4 37  1  0
  4 38  1  0
  6 39  1  0
  6 40  1  0
  7 41  1  0
  7 42  1  0
 20 50  1  1
 21 51  1  0
 21 52  1  0
 22 53  1  6
 24 54  1  0
 26 55  1  0
 26 56  1  0
 26 57  1  0
 30 58  1  0
 30 59  1  0
 30 60  1  0
 10 43  1  0
 13 44  1  0
 14 45  1  0
 15 46  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
M  END


  Mrv1652309072205162D          

 30 33  0  0  1  0            999 V2000
    0.6034   -0.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4720   -0.1260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2494    0.3170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0779    1.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    1.6761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6910    2.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4756    2.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9605    2.0886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4455    2.7560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4840    3.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    2.5011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2301    1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8432    1.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6716    0.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8870    0.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739    0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5532    0.0931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8401    0.8459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455    1.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4756    1.4211    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6471    0.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0340    0.0621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8842   -0.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6486   -1.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8501   -1.9522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6302   -2.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1718   -1.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316   -2.3474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819   -1.8800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2518   -2.6596    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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 12 19  1  0  0  0  0
  8 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20  5  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  1  0  0  0
 23 24  2  0  0  0  0
 24 25  1  4  0  0  0
 25 26  1  0  0  0  0
 23 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242849

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1CN2CC[C@@]3([C@@H]2C[C@H]1C(=COC)C(=O)OC)C(O)=NC1=CC=CC(OC)=C31

> <INCHI_IDENTIFIER>
InChI=1S/C23H30N2O5/c1-5-14-12-25-10-9-23(19(25)11-15(14)16(13-28-2)21(26)30-4)20-17(24-22(23)27)7-6-8-18(20)29-3/h6-8,13-15,19H,5,9-12H2,1-4H3,(H,24,27)/t14-,15-,19+,23+/m1/s1

> <INCHI_KEY>
GOOQGTUGASFJCR-CPMLIZHXSA-N

> <FORMULA>
C23H30N2O5

> <MOLECULAR_WEIGHT>
414.502

> <EXACT_MASS>
414.215472074

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
44.47157914891935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(3R,6'S,7'R,8'aS)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate

> <JCHEM_LOGP>
0.4482675964726415

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.571460351250181

> <JCHEM_PKA_STRONGEST_BASIC>
10.855400485037935

> <JCHEM_POLAR_SURFACE_AREA>
80.59000000000002

> <JCHEM_REFRACTIVITY>
115.22429999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[(3R,6'S,7'R,8'aS)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-7'-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       1.126  -0.118   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.748  -0.235   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.199   0.592   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.879   2.098   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       5.023   3.129   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.023   4.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.488   5.145   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.393   3.899   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.298   5.145   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.370   6.722   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       9.763   4.669   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       9.763   3.129   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.907   2.098   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.587   0.592   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.122   0.116   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.978   1.146   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.633   0.174   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.301   1.579   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.298   2.653   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.488   2.653   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.808   1.146   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.664   0.116   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.384  -1.667   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.944  -3.257   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.453  -3.644   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.043  -5.128   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.921  -3.218   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.912  -4.382   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       7.433  -3.509   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.937  -4.965   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   19   20                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   12    8                                                  
CONECT   20    8    5   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    3   23                                                  
CONECT   23   22   24   27                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   23   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[(3R,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoic acid	Generator

Chemical Formula

C₂₃H₃₀N₂O₅

Average Mass

414.5020 Da

Monoisotopic Mass

414.21547 Da

IUPAC Name

methyl 2-[(3R,6'S,7'R,8'aS)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate

Traditional Name

methyl 2-[(3R,6'S,7'R,8'aS)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl]-3-methoxyprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC[C@@H]1CN2CC[C@@]3([C@@H]2C[C@H]1C(=COC)C(=O)OC)C(O)=NC1=CC=CC(OC)=C31

InChI Identifier

InChI=1S/C23H30N2O5/c1-5-14-12-25-10-9-23(19(25)11-15(14)16(13-28-2)21(26)30-4)20-17(24-22(23)27)7-6-8-18(20)29-3/h6-8,13-15,19H,5,9-12H2,1-4H3,(H,24,27)/t14-,15-,19+,23+/m1/s1

InChI Key

GOOQGTUGASFJCR-CPMLIZHXSA-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 rotundifolia	LOTUS Database	35616633
Mitragyna tubulosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Indolizidine
Anisole
Aralkylamine
Alkyl aryl ether
Benzenoid
N-alkylpyrrolidine
Piperidine
Vinylogous ester
Cyclic carboximidic acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid ester
Amino acid or derivatives
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic 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	0.45	ChemAxon
pKa (Strongest Acidic)	3.57	ChemAxon
pKa (Strongest Basic)	10.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.59 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	115.22 m³·mol⁻¹	ChemAxon
Polarizability	44.47 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

162890762

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate (NP0242849)

MOL for NP0242849 (methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

3D MOL for NP0242849 (methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

3D SDF for NP0242849 (methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

3D-SDF for NP0242849 (methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

PDB for NP0242849 (methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

3D PDB for NP0242849 (methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

SMILES for NP0242849 (methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

INCHI for NP0242849 (methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

Structure for NP0242849 (methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)

3D Structure for NP0242849 (methyl 2-[(3r,6's,7'r,8'as)-6'-ethyl-2-hydroxy-4-methoxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl]-3-methoxyprop-2-enoate)