NP-MRD: Showing NP-Card for 1,9a-seco-stemoenonine (NP0033859)

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Record Information

Version

2.0

Created at

2021-06-20 17:45:27 UTC

Updated at

2021-06-30 00:03:53 UTC

NP-MRD ID

NP0033859

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,9a-seco-stemoenonine

Provided By

JEOL Database JEOL Logo

Description

1,9a-seco-stemoenonine is found in Stemona tuberosa. 1,9a-seco-stemoenonine was first documented in 2008 ( Lin, L. -G., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202119453D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306202119453D          

 58 61  0  0  0  0            999 V2000
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   -0.8776   -3.6490    4.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3912   -2.8130    4.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4428   -1.6806    3.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0246   -0.7473    3.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7574   -2.2993    1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9046   -0.8362    1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842    4.3747   -0.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7645    5.4110    0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1662    1.8675    0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255    1.1389   -2.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6686    0.0201   -1.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8084    1.0899   -1.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    1.4551   -4.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0066   -0.0717   -3.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0247    1.3378   -4.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428    0.7890    0.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3585    1.9141   -0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1212    0.1034   -1.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3740   -0.0404   -2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294   -1.6310   -0.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428   -2.2204   -1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7911   -1.8963   -0.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452   -5.0122    1.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991   -7.2920    2.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8466   -7.5510    2.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1561   -6.9091    4.3425 H   0  0  0  0  0  0  0  0  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
 20 21  1  0  0  0  0
  8 13  1  0  0  0  0
 13 19  1  0  0  0  0
 22 21  1  0  0  0  0
 23  4  1  0  0  0  0
 27 29  1  0  0  0  0
 29 31  1  0  0  0  0
 19 17  1  0  0  0  0
 17 15  1  0  0  0  0
 15 14  1  0  0  0  0
 14 13  1  0  0  0  0
 25 31  1  1  0  0  0
 17 18  2  0  0  0  0
  4  5  1  0  0  0  0
 10 11  2  0  0  0  0
  4  3  1  0  0  0  0
 29 30  2  0  0  0  0
  3 25  1  0  0  0  0
 27 28  1  0  0  0  0
 25 24  1  0  0  0  0
  3  2  1  0  0  0  0
 24 23  1  0  0  0  0
  2  1  1  0  0  0  0
  5  7  1  0  0  0  0
  4 38  1  1  0  0  0
 25 26  1  0  0  0  0
 13 41  1  1  0  0  0
  7 20  1  0  0  0  0
 23 54  1  6  0  0  0
 15 16  1  0  0  0  0
 23 22  1  0  0  0  0
  5  6  2  0  0  0  0
 26 27  2  0  0  0  0
 10 12  1  0  0  0  0
 26 55  1  0  0  0  0
 20 48  1  0  0  0  0
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 21 50  1  0  0  0  0
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  3 37  1  6  0  0  0
  9 39  1  0  0  0  0
 15 44  1  1  0  0  0
 14 42  1  0  0  0  0
 14 43  1  0  0  0  0
 28 56  1  0  0  0  0
 28 57  1  0  0  0  0
 28 58  1  0  0  0  0
  2 35  1  0  0  0  0
  2 36  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
 16 45  1  0  0  0  0
 16 46  1  0  0  0  0
 16 47  1  0  0  0  0
 12 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0033859

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(\[H])=C(/N1C(=O)[C@]2([H])[C@]([H])(O[C@@]3(OC(=O)C(=C3[H])C([H])([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])C1([H])[H])[C@@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H27NO8/c1-4-13-18-15(30-22(13)10-12(3)21(28)31-22)6-5-7-23(19(18)26)14(9-17(24)25)16-8-11(2)20(27)29-16/h9-11,13,15-16,18H,4-8H2,1-3H3,(H,24,25)/b14-9-/t11-,13-,15+,16-,18-,22-/m0/s1

> <INCHI_KEY>
JUYMQCOCANDESC-ILJPQRDMSA-N

> <FORMULA>
C22H27NO8

> <MOLECULAR_WEIGHT>
433.457

> <EXACT_MASS>
433.173666833

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
44.63727447178138

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-[(2R,3'S,3'aS,8'aR)-3'-ethyl-4-methyl-4',5-dioxo-3',3'a,4',5',6',7',8',8'a-octahydro-5H-spiro[furan-2,2'-furo[3,2-c]azepine]-5'-yl]-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]prop-2-enoic acid

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
2.258113771333332

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.671336301212722

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6360125605951965

> <JCHEM_PKA_STRONGEST_BASIC>
-4.302812014583364

> <JCHEM_POLAR_SURFACE_AREA>
119.44000000000001

> <JCHEM_REFRACTIVITY>
107.7368

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-[(2R,3'S,3'aS,8'aR)-3'-ethyl-4-methyl-4',5-dioxo-3',3'a,6',7',8',8'a-hexahydrospiro[furan-2,2'-furo[3,2-c]azepine]-5'-yl]-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
   -1.3556   -2.6707    4.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6032   -1.7544    3.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977   -2.1799    2.1723 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0573   -1.1476    1.2382 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9188    0.0683    0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0749    0.1233    1.3743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3258    1.0948    0.1957 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0594    2.2680   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5705    3.5195    0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874    3.9262    0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4364    3.2581    1.3916 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329    5.2212    0.4474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    2.0817   -0.5965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6480    1.0510   -1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9588    1.4592   -2.3440 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0688    1.0182   -3.7909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8985    2.9542   -2.1898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5446    3.7705   -2.8248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0114    3.2834   -1.2055 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0578    0.9736   -0.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052   -0.1036   -1.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158   -1.5263   -0.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078   -1.9529   -0.0414 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2523   -3.3306    0.3347 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0731   -3.4348    1.7508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5621   -4.7332    2.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559   -5.5118    2.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -6.8881    3.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771   -4.7301    2.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4503   -5.1103    3.5924 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3433   -3.5063    2.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739   -2.2319    5.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8776   -3.6490    4.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3912   -2.8130    4.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4428   -1.6806    3.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0246   -0.7473    3.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7574   -2.2993    1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9046   -0.8362    1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842    4.3747   -0.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7645    5.4110    0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1662    1.8675    0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255    1.1389   -2.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6686    0.0201   -1.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8084    1.0899   -1.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    1.4551   -4.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0066   -0.0717   -3.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0247    1.3378   -4.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428    0.7890    0.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3585    1.9141   -0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1212    0.1034   -1.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3740   -0.0404   -2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294   -1.6310   -0.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428   -2.2204   -1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7911   -1.8963   -0.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452   -5.0122    1.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991   -7.2920    2.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8466   -7.5510    2.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1561   -6.9091    4.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 20 21  1  0
  8 13  1  0
 13 19  1  0
 22 21  1  0
 23  4  1  0
 27 29  1  0
 29 31  1  0
 19 17  1  0
 17 15  1  0
 15 14  1  0
 14 13  1  0
 25 31  1  1
 17 18  2  0
  4  5  1  0
 10 11  2  0
  4  3  1  0
 29 30  2  0
  3 25  1  0
 27 28  1  0
 25 24  1  0
  3  2  1  0
 24 23  1  0
  2  1  1  0
  5  7  1  0
  4 38  1  1
 25 26  1  0
 13 41  1  1
  7 20  1  0
 23 54  1  6
 15 16  1  0
 23 22  1  0
  5  6  2  0
 26 27  2  0
 10 12  1  0
 26 55  1  0
 20 48  1  0
 20 49  1  0
 22 52  1  0
 22 53  1  0
 21 50  1  0
 21 51  1  0
  3 37  1  6
  9 39  1  0
 15 44  1  1
 14 42  1  0
 14 43  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
  2 35  1  0
  2 36  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 12 40  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.356  -2.671   4.598  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.603  -1.754   3.646  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.698  -2.180   2.172  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.057  -1.148   1.238  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.919   0.068   0.952  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.075   0.123   1.374  0.00  0.00           O+0
HETATM    7  N   UNK     0      -0.326   1.095   0.196  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.059   2.268  -0.094  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.571   3.519   0.059  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.687   3.926   0.707  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.436   3.258   1.392  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.933   5.221   0.447  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.501   2.082  -0.597  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.648   1.051  -1.705  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.959   1.459  -2.344  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.069   1.018  -3.791  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.898   2.954  -2.190  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.545   3.771  -2.825  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.011   3.283  -1.206  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.058   0.974  -0.320  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.205  -0.104  -1.401  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.316  -1.526  -0.862  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.108  -1.953  -0.041  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.252  -3.331   0.335  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.073  -3.435   1.751  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.562  -4.733   2.040  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.256  -5.512   2.745  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.080  -6.888   3.251  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.477  -4.730   2.967  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.450  -5.110   3.592  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.343  -3.506   2.389  0.00  0.00           O+0
HETATM   32  H   UNK     0      -1.374  -2.232   5.601  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.878  -3.649   4.681  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.391  -2.813   4.274  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.443  -1.681   3.965  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.025  -0.747   3.753  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.757  -2.299   1.904  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.905  -0.836   1.662  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.184   4.375  -0.214  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.765   5.411   0.930  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.166   1.867   0.248  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.825   1.139  -2.427  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.669   0.020  -1.340  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.808   1.090  -1.758  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.275   1.455  -4.407  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.007  -0.072  -3.872  0.00  0.00           H+0
HETATM   47  H   UNK     0      -5.025   1.338  -4.220  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.743   0.789   0.514  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.359   1.914  -0.793  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.121   0.103  -1.968  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.374  -0.040  -2.113  0.00  0.00           H+0
HETATM   52  H   UNK     0       2.229  -1.631  -0.262  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.443  -2.220  -1.702  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.791  -1.896  -0.669  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.545  -5.012   1.693  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.899  -7.292   2.974  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.847  -7.551   2.838  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.156  -6.909   4.343  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    3    1   35   36                                             
CONECT    3    4   25    2   37                                             
CONECT    4   23    5    3   38                                             
CONECT    5    4    7    6                                                  
CONECT    6    5                                                            
CONECT    7    8    5   20                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   39                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   40                                                       
CONECT   13    8   19   14   41                                             
CONECT   14   15   13   42   43                                             
CONECT   15   17   14   16   44                                             
CONECT   16   15   45   46   47                                             
CONECT   17   19   15   18                                                  
CONECT   18   17                                                            
CONECT   19   13   17                                                       
CONECT   20   21    7   48   49                                             
CONECT   21   20   22   50   51                                             
CONECT   22   21   23   52   53                                             
CONECT   23    4   24   54   22                                             
CONECT   24   25   23                                                       
CONECT   25   31    3   24   26                                             
CONECT   26   25   27   55                                                  
CONECT   27   29   28   26                                                  
CONECT   28   27   56   57   58                                             
CONECT   29   27   31   30                                                  
CONECT   30   29                                                            
CONECT   31   29   25                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    2                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    9                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   15                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
CONECT   55   26                                                            
CONECT   56   28                                                            
CONECT   57   28                                                            
CONECT   58   28                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  122    0
END

RDKit          3D

58 61  0  0  0  0  0  0  0  0999 V2000
   -1.3556   -2.6707    4.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6032   -1.7544    3.6458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6977   -2.1799    2.1723 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0573   -1.1476    1.2382 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9188    0.0683    0.9520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0749    0.1233    1.3743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3258    1.0948    0.1957 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0594    2.2680   -0.0939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5705    3.5195    0.0585 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6874    3.9262    0.7072 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4364    3.2581    1.3916 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329    5.2212    0.4474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012    2.0817   -0.5965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6480    1.0510   -1.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9588    1.4592   -2.3440 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.0114    3.2834   -1.2055 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0578    0.9736   -0.3201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052   -0.1036   -1.4008 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158   -1.5263   -0.8619 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078   -1.9529   -0.0414 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2523   -3.3306    0.3347 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0731   -3.4348    1.7508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5621   -4.7332    2.0401 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2559   -5.5118    2.7449 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0801   -6.8881    3.2508 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4771   -4.7301    2.9674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4503   -5.1103    3.5924 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3433   -3.5063    2.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739   -2.2319    5.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8776   -3.6490    4.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3912   -2.8130    4.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4428   -1.6806    3.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0246   -0.7473    3.7526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7574   -2.2993    1.9035 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9046   -0.8362    1.6617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842    4.3747   -0.2142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7645    5.4110    0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1662    1.8675    0.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8255    1.1389   -2.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6686    0.0201   -1.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8084    1.0899   -1.7583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    1.4551   -4.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0066   -0.0717   -3.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0247    1.3378   -4.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7428    0.7890    0.5137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3585    1.9141   -0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1212    0.1034   -1.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3740   -0.0404   -2.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2294   -1.6310   -0.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428   -2.2204   -1.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7911   -1.8963   -0.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452   -5.0122    1.6929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991   -7.2920    2.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8466   -7.5510    2.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1561   -6.9091    4.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 20 21  1  0
  8 13  1  0
 13 19  1  0
 22 21  1  0
 23  4  1  0
 27 29  1  0
 29 31  1  0
 19 17  1  0
 17 15  1  0
 15 14  1  0
 14 13  1  0
 25 31  1  1
 17 18  2  0
  4  5  1  0
 10 11  2  0
  4  3  1  0
 29 30  2  0
  3 25  1  0
 27 28  1  0
 25 24  1  0
  3  2  1  0
 24 23  1  0
  2  1  1  0
  5  7  1  0
  4 38  1  1
 25 26  1  0
 13 41  1  1
  7 20  1  0
 23 54  1  6
 15 16  1  0
 23 22  1  0
  5  6  2  0
 26 27  2  0
 10 12  1  0
 26 55  1  0
 20 48  1  0
 20 49  1  0
 22 52  1  0
 22 53  1  0
 21 50  1  0
 21 51  1  0
  3 37  1  6
  9 39  1  0
 15 44  1  1
 14 42  1  0
 14 43  1  0
 28 56  1  0
 28 57  1  0
 28 58  1  0
  2 35  1  0
  2 36  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
 12 40  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇NO₈

Average Mass

433.4570 Da

Monoisotopic Mass

433.17367 Da

IUPAC Name

(2Z)-3-[(2R,3'S,3'aS,8'aR)-3'-ethyl-4-methyl-4',5-dioxo-3',3'a,4',5',6',7',8',8'a-octahydro-5H-spiro[furan-2,2'-furo[3,2-c]azepine]-5'-yl]-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]prop-2-enoic acid

Traditional Name

(2Z)-3-[(2R,3'S,3'aS,8'aR)-3'-ethyl-4-methyl-4',5-dioxo-3',3'a,6',7',8',8'a-hexahydrospiro[furan-2,2'-furo[3,2-c]azepine]-5'-yl]-3-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]prop-2-enoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(\[H])=C(/N1C(=O)[C@]2([H])[C@]([H])(O[C@@]3(OC(=O)C(=C3[H])C([H])([H])[H])[C@@]2([H])C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])C1([H])[H])[C@@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])C1([H])[H]

InChI Identifier

InChI=1S/C22H27NO8/c1-4-13-18-15(30-22(13)10-12(3)21(28)31-22)6-5-7-23(19(18)26)14(9-17(24)25)16-8-11(2)20(27)29-16/h9-11,13,15-16,18H,4-8H2,1-3H3,(H,24,25)/b14-9-/t11-,13-,15+,16-,18-,22-/m0/s1

InChI Key

JUYMQCOCANDESC-ILJPQRDMSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Stemona tuberosa	JEOL database	Lin, L. -G., et al, J. Nat. Prod. 71, 1107 (2008)

Chemical Taxonomy

Classification

Not classified

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	1.7	ALOGPS
logP	2.26	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	119.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.74 m³·mol⁻¹	ChemAxon
Polarizability	44.64 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

Not Available

References

General References

Lin, L. -G., et al. (2008). Lin, L. -G., et al, J. Nat. Prod. 71, 1107 (2008). J. Nat. Prod..

Showing NP-Card for 1,9a-seco-stemoenonine (NP0033859)

MOL for NP0033859 (1,9a-seco-stemoenonine)

3D MOL for NP0033859 (1,9a-seco-stemoenonine)

3D SDF for NP0033859 (1,9a-seco-stemoenonine)

3D-SDF for NP0033859 (1,9a-seco-stemoenonine)

PDB for NP0033859 (1,9a-seco-stemoenonine)

3D PDB for NP0033859 (1,9a-seco-stemoenonine)

SMILES for NP0033859 (1,9a-seco-stemoenonine)

INCHI for NP0033859 (1,9a-seco-stemoenonine)

Structure for NP0033859 (1,9a-seco-stemoenonine)

3D Structure for NP0033859 (1,9a-seco-stemoenonine)