NP-MRD: Showing NP-Card for (1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate (NP0174363)

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Record Information

Version

2.0

Created at

2022-09-03 11:36:14 UTC

Updated at

2022-09-03 11:36:14 UTC

NP-MRD ID

NP0174363

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate

Description

(1R)-1-[(1'R,2'R,3S,5'S,6'S,8'R,11'S)-1-methoxy-4'-methyl-2-oxo-1,2-dihydro-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]Dodecane]-2'-yl]ethyl acetate belongs to the class of organic compounds known as gelsemium alkaloids. These are alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21. (1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate is found in Gelsemium rankinii. Based on a literature review very few articles have been published on (1R)-1-[(1'R,2'R,3S,5'S,6'S,8'R,11'S)-1-methoxy-4'-methyl-2-oxo-1,2-dihydro-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]Dodecane]-2'-yl]ethyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032213362D          

 30 35  0  0  1  0            999 V2000
    3.8101   -3.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0842   -2.8217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682   -1.9095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2116   -1.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7435   -2.2860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4622   -0.6743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2849   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897    0.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6072   -0.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9199   -0.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4152   -1.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5976   -1.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500   -0.6928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5561   -0.1145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9603    0.5988    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4771    1.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3338    1.1527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6568    0.3092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2869   -0.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4006   -0.0154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0451   -0.9772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3600   -1.8020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2534   -2.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868   -2.4112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0985   -2.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7102   -2.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2720   -1.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2200   -1.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1366   -0.5471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969   -0.3150    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  2  0  0  0  0
  6  4  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  3 12  1  0  0  0  0
 13  6  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  6 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 19  1  1  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 14 29  1  6  0  0  0
 29 30  1  0  0  0  0
M  END

     RDKit          3D

 58 63  0  0  0  0  0  0  0  0999 V2000
    3.2086    3.6593   -0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0632    3.0883   -0.8280 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9232    1.8392   -0.3456 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9874    1.4523    0.6478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4387    2.2854    1.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8443   -0.0130    0.5390 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.9573   -1.5371   -0.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8499    0.5987   -1.4973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6914    0.6810   -0.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1571   -0.4077   -0.5214 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0928   -1.9483   -0.5955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8022   -2.3334    0.6528 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0754   -2.8218    1.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0368   -1.8910    2.0534 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071   -0.5862    1.8827 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8551   -0.4565    2.2041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6318   -1.1102    1.0988 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5865   -0.3444   -0.2035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4155    0.8161   -0.3613 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8466    0.4065    0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1797    2.0206    0.2257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1470    3.1944   -0.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8888    4.5049    0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3360    3.1697   -1.7464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1679   -1.3846   -1.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0471   -2.1363   -1.7034 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3257   -3.5279   -1.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9247    3.9769   -1.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375    4.5366    0.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7648    2.9596    0.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5018   -0.6339   -2.1447 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1827    1.4494   -2.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8571   -2.3599   -0.8151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5565   -3.1292    0.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5879   -3.0597    2.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5715   -3.7449    1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1694    0.0328    2.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1216   -0.9548    3.1594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792    0.6099    2.3332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6398   -1.4029    1.4029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5617    0.9859   -1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2166   -0.4273   -0.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8612    0.2120    1.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5320    1.2724   -0.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7528    4.6612    0.8493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9267    4.5478    0.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9845    5.3205   -0.6016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8786   -2.0473   -0.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7225   -0.8639   -2.0258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5425   -4.1428   -1.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525   -3.6881   -3.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3289   -3.8422   -1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 25 27  2  0
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 11 12  2  0
 12  3  1  0
 18  6  1  0
 12  7  1  0
 21 13  1  0
 29 14  1  0
 20 15  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
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 16 42  1  0
 18 43  1  1
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 28 54  1  0
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 30 56  1  0
 30 57  1  0
 30 58  1  0
 22 47  1  6
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 26 51  1  0
 26 52  1  0
 26 53  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
M  END


  Mrv1652309032213362D          

 30 35  0  0  1  0            999 V2000
    3.8101   -3.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0842   -2.8217    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9682   -1.9095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2116   -1.3728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7435   -2.2860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4622   -0.6743    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2849   -0.6128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897    0.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6072   -0.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9199   -0.8345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4152   -1.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5976   -1.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4500   -0.6928    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5561   -0.1145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9603    0.5988    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4771    1.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3338    1.1527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6568    0.3092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2869   -0.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4006   -0.0154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0451   -0.9772    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3600   -1.8020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2534   -2.0847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6868   -2.4112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0985   -2.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7102   -2.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2720   -1.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2200   -1.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1366   -0.5471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969   -0.3150    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  2  0  0  0  0
  6  4  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
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  7 12  1  0  0  0  0
  3 12  1  0  0  0  0
 13  6  1  6  0  0  0
 13 14  1  0  0  0  0
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 29 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0174363

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C(=O)[C@@]2([C@H]3[C@H]4[C@H]5CO[C@@H]2C[C@H]5[C@@]3(CN4C)[C@@H](C)OC(C)=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C23H28N2O5/c1-12(30-13(2)26)22-11-24(3)19-14-10-29-18(9-16(14)22)23(20(19)22)15-7-5-6-8-17(15)25(28-4)21(23)27/h5-8,12,14,16,18-20H,9-11H2,1-4H3/t12-,14+,16-,18-,19-,20+,22-,23+/m1/s1

> <INCHI_KEY>
BTZWFBFZHHQPCI-MRJFZWFPSA-N

> <FORMULA>
C23H28N2O5

> <MOLECULAR_WEIGHT>
412.486

> <EXACT_MASS>
412.19982201

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.34540517800031

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R)-1-[(1'R,2'R,3S,5'S,6'S,8'R,11'S)-1-methoxy-4'-methyl-2-oxo-1,2-dihydro-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^{2,6}.0^{5,11}]dodecane]-2'-yl]ethyl acetate

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
0.8690387339999999

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.605257140407156

> <JCHEM_POLAR_SURFACE_AREA>
68.30999999999999

> <JCHEM_REFRACTIVITY>
107.9306

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R)-1-[(1'R,2'R,3S,5'S,6'S,8'R,11'S)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^{2,6}.0^{5,11}]dodecane]-2'-yl]ethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       7.112  -6.140   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.757  -5.267   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       5.541  -3.564   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.128  -2.562   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.255  -4.267   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.596  -1.259   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.132  -1.144   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.074   0.074   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.600  -0.133   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.184  -1.558   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.242  -2.776   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.716  -2.569   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.707  -1.293   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.038  -0.214   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.792   1.118   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.757   2.375   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.356   2.152   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.959   0.577   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.269  -0.176   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.615  -0.029   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.951  -1.824   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.539  -3.364   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.206  -3.891   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.282  -4.501   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.184  -4.029   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.326  -5.062   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.508  -2.523   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.411  -2.402   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0      -0.255  -1.021   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      -1.861  -0.588   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   13   18                                             
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7    3                                                  
CONECT   13    6   14   21                                                  
CONECT   14   13   15   29                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    6   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   15   21                                                  
CONECT   21   20   13   22   28                                             
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   21   29                                                       
CONECT   29   28   14   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Value	Source
(1R)-1-[(1'r,2'r,3S,5's,6's,8'r,11's)-1-Methoxy-4'-methyl-2-oxo-1,2-dihydro-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0,.0,]dodecane]-2'-yl]ethyl acetic acid	Generator

Chemical Formula

C₂₃H₂₈N₂O₅

Average Mass

412.4860 Da

Monoisotopic Mass

412.19982 Da

IUPAC Name

(1R)-1-[(1'R,2'R,3S,5'S,6'S,8'R,11'S)-1-methoxy-4'-methyl-2-oxo-1,2-dihydro-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^{2,6}.0^{5,11}]dodecane]-2'-yl]ethyl acetate

Traditional Name

(1R)-1-[(1'R,2'R,3S,5'S,6'S,8'R,11'S)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0^{2,6}.0^{5,11}]dodecane]-2'-yl]ethyl acetate

CAS Registry Number

Not Available

SMILES

CON1C(=O)[C@@]2([C@H]3[C@H]4[C@H]5CO[C@@H]2C[C@H]5[C@@]3(CN4C)[C@@H](C)OC(C)=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C23H28N2O5/c1-12(30-13(2)26)22-11-24(3)19-14-10-29-18(9-16(14)22)23(20(19)22)15-7-5-6-8-17(15)25(28-4)21(23)27/h5-8,12,14,16,18-20H,9-11H2,1-4H3/t12-,14+,16-,18-,19-,20+,22-,23+/m1/s1

InChI Key

BTZWFBFZHHQPCI-MRJFZWFPSA-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
Gelsemium rankinii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gelsemium alkaloids. These are alkaloids with a structure that is based on the tetracyclic gelsemium skeleton. These alkaloids contain an oxindole function and a cage-like, hydroaromatic residue which is believed to arise from an intermediate related to anhydrovobasinediol by formation of a 6,20 bond and rearrangement to an oxindole. The major alkaloids in this group are related to Gelsemine; however, a smaller group, characterized by Gelsedine, lack the 6,20 bond, and have also lost C-21.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Gelsemium alkaloids

Sub Class

Not Available

Direct Parent

Gelsemium alkaloids

Alternative Parents

Substituents

Gelsemium skeleton
Indole or derivatives
Isoindoline
Isoindole or derivatives
Oxepane
Aralkylamine
Oxane
Piperidine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Carboxylic acid ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Oxacycle
Carboxylic acid derivative
Azacycle
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Amine
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.8	ALOGPS
logP	0.87	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	9.61	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	68.31 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.93 m³·mol⁻¹	ChemAxon
Polarizability	43.35 Å³	ChemAxon
Number of Rings	6	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

162918477

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate (NP0174363)

MOL for NP0174363 ((1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate)

3D MOL for NP0174363 ((1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate)

3D SDF for NP0174363 ((1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate)

3D-SDF for NP0174363 ((1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate)

PDB for NP0174363 ((1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate)

3D PDB for NP0174363 ((1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate)

SMILES for NP0174363 ((1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate)

INCHI for NP0174363 ((1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate)

Structure for NP0174363 ((1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate)

3D Structure for NP0174363 ((1r)-1-[(1'r,2'r,3s,5's,6's,8'r,11's)-1-methoxy-4'-methyl-2-oxo-9'-oxa-4'-azaspiro[indole-3,7'-tetracyclo[6.3.1.0²,⁶.0⁵,¹¹]dodecan]-2'-yl]ethyl acetate)