NP-MRD: Showing NP-Card for methyl 2-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate (NP0277516)

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Record Information

Version

2.0

Created at

2022-09-09 02:11:00 UTC

Updated at

2022-09-09 02:11:00 UTC

NP-MRD ID

NP0277516

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate

Description

Methyl 2-{6'-ethyl-2,4-dihydroxy-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-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate is found in Fleroya ledermannii, Mitragyna parvifolia, Mitragyna speciosa and Mitragyna tubulosa. Methyl 2-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl}-3-methoxyprop-2-enoate is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151514182D          

 29 32  0  0  0  0            999 V2000
    4.9213    1.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367    1.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820   -0.3945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820   -1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974   -1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7390    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5675    2.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1805    2.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0090    3.3854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6221    3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7828    2.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1697    1.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6113    3.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8267    3.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3276   -1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5825   -2.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5429   -1.2195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5429   -0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0702    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2837    0.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3276   -0.1395    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  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  4  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
  8 29  1  0  0  0  0
 23 29  1  0  0  0  0
M  END

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    0.9001    4.5345   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9469    3.3007    0.1815 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785    2.0674   -0.6607 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3590    1.8766   -1.7697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9629    1.7374   -1.1926 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8876    1.3755   -2.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9039    0.4460   -1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0555   -0.2344   -0.5049 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3675   -1.4256   -1.0447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5881   -1.4737   -2.0648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7304   -2.5207   -0.2205 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6268   -2.1021    0.8008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2742   -2.7761    1.8391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1193   -2.1228    2.7031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3199   -0.7713    2.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6868   -0.0920    1.5033 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9005    1.2690    1.3387 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316   -0.7524    0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0697    0.8619   -0.0916 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1549    0.2348    0.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741    0.9083    0.2410 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4271   -0.1850   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0377   -0.0351   -1.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9066   -0.7519   -2.0592 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5789   -1.8876   -2.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939   -1.3302    0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9091   -1.3015    1.7646 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3706   -2.4121    0.4945 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -3.5020    1.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3882    5.3965   -0.1886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1290    4.7627   -1.0411 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5489    4.3131   -1.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7181    3.4587    0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0474    3.1694    0.6105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3214    2.3959   -1.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5234    1.0170   -2.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3547    2.7946   -2.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4026    0.7794   -3.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3640    2.2388   -2.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2807   -0.3257   -2.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7606    0.9864   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3834   -3.5121   -0.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1029   -3.8333    1.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6365   -2.6167    3.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9907   -0.2252    3.2017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236    1.7319    1.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6448    1.4245    0.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2226   -0.8005   -0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0517    0.0427    1.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8611    1.2729    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7881    0.9360   -1.9387 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9669   -2.8362   -2.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1976   -2.0743   -3.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3137   -1.9468   -1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4828   -4.4356    0.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5289   -3.5198    1.8489 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7636   -3.5297    2.1717 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 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
  8  9  1  6
  9 10  2  0
  9 11  1  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
 16 18  2  0
 21  3  1  0
 18 12  1  0
 19  5  1  0
 18  8  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  6
  4 36  1  0
  4 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
 19 47  1  1
 20 48  1  0
 20 49  1  0
 21 50  1  1
 23 51  1  0
 25 52  1  0
 25 53  1  0
 25 54  1  0
 29 55  1  0
 29 56  1  0
 29 57  1  0
 11 42  1  0
 13 43  1  0
 14 44  1  0
 15 45  1  0
 17 46  1  0
M  END


  Mrv1533004151514182D          

 29 32  0  0  0  0            999 V2000
    4.9213    1.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1367    1.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5236    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6951    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820   -0.3945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0820   -1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974   -1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -0.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2974   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1259    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7390    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5675    2.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1805    2.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0090    3.3854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6221    3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7828    2.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1697    1.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6113    3.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8267    3.3433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3276   -1.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5825   -2.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5429   -1.2195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5429   -0.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0702    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8860    1.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2837    0.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3276   -0.1395    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  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  4  0  0  0
 14 15  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
  8 29  1  0  0  0  0
 23 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0277516

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1CN2CCC3(C2CC1C(=COC)C(=O)OC)C(=O)NC1=CC=CC(O)=C31

> <INCHI_IDENTIFIER>
InChI=1S/C22H28N2O5/c1-4-13-11-24-9-8-22(19-16(23-21(22)27)6-5-7-17(19)25)18(24)10-14(13)15(12-28-2)20(26)29-3/h5-7,12-14,18,25H,4,8-11H2,1-3H3,(H,23,27)

> <INCHI_KEY>
IXWWTVSMMIIIFZ-UHFFFAOYSA-N

> <FORMULA>
C22H28N2O5

> <MOLECULAR_WEIGHT>
400.475

> <EXACT_MASS>
400.19982201

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.037465885816275

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-{6'-ethyl-4-hydroxy-2-oxo-1,2,3',5',6',7',8',8'a-octahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl}-3-methoxyprop-2-enoate

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
1.0381965892996747

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.366670051410907

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.842946912869285

> <JCHEM_PKA_STRONGEST_BASIC>
10.24717958621233

> <JCHEM_POLAR_SURFACE_AREA>
88.1

> <JCHEM_REFRACTIVITY>
109.98689999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-{6'-ethyl-4-hydroxy-2-oxo-3',5',6',7',8',8'a-hexahydro-1H,2'H-spiro[indole-3,1'-indolizine]-7'-yl}-3-methoxyprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       9.186   2.355   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.722   2.831   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.577   1.800   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.898   0.294   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       5.753  -0.736   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.753  -2.276   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.289  -2.752   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.383  -1.506   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.289  -0.260   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.968   1.246   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.113   2.276   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.793   3.783   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.937   4.813   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.617   6.320   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.761   7.350   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.328   4.259   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.184   3.228   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.008   5.765   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.543   6.241   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.478  -2.752   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.954  -4.217   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       1.013  -2.276   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       1.013  -0.736   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.131   0.294   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.189   1.800   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.654   2.276   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.798   1.246   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.263   1.722   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.478  -0.260   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   20   29                                             
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   12   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20    8   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27    8   23                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-{6'-ethyl-2,4-dihydroxy-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

C₂₂H₂₈N₂O₅

Average Mass

400.4750 Da

Monoisotopic Mass

400.19982 Da

IUPAC Name

methyl 2-{6'-ethyl-4-hydroxy-2-oxo-1,2,3',5',6',7',8',8'a-octahydro-2'H-spiro[indole-3,1'-indolizine]-7'-yl}-3-methoxyprop-2-enoate

Traditional Name

methyl 2-{6'-ethyl-4-hydroxy-2-oxo-3',5',6',7',8',8'a-hexahydro-1H,2'H-spiro[indole-3,1'-indolizine]-7'-yl}-3-methoxyprop-2-enoate

CAS Registry Number

Not Available

SMILES

CCC1CN2CCC3(C2CC1C(=COC)C(=O)OC)C(=O)NC1=CC=CC(O)=C31

InChI Identifier

InChI=1S/C22H28N2O5/c1-4-13-11-24-9-8-22(19-16(23-21(22)27)6-5-7-17(19)25)18(24)10-14(13)15(12-28-2)20(26)29-3/h5-7,12-14,18,25H,4,8-11H2,1-3H3,(H,23,27)

InChI Key

IXWWTVSMMIIIFZ-UHFFFAOYSA-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
Fleroya ledermannii	LOTUS Database	35616633
Mitragyna parvifolia	LOTUS Database	35616633
Mitragyna speciosa	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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Cyclic carboximidic acid
Carboxylic acid ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
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	2.64	ALOGPS
logP	1.04	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.84	ChemAxon
pKa (Strongest Basic)	10.25	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.1 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	109.99 m³·mol⁻¹	ChemAxon
Polarizability	43.04 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

634020

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-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate (NP0277516)

MOL for NP0277516 (methyl 2-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate)

3D MOL for NP0277516 (methyl 2-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate)

3D SDF for NP0277516 (methyl 2-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate)

3D-SDF for NP0277516 (methyl 2-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate)

PDB for NP0277516 (methyl 2-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate)

3D PDB for NP0277516 (methyl 2-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate)

SMILES for NP0277516 (methyl 2-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate)

INCHI for NP0277516 (methyl 2-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate)

Structure for NP0277516 (methyl 2-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate)

3D Structure for NP0277516 (methyl 2-{6'-ethyl-2,4-dihydroxy-3',5',6',7',8',8'a-hexahydro-2'h-spiro[indole-3,1'-indolizin]-7'-yl}-3-methoxyprop-2-enoate)