NP-MRD: Showing NP-Card for (1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione (NP0278654)

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Record Information

Version

1.0

Created at

2022-09-09 03:45:34 UTC

Updated at

2022-09-09 03:45:34 UTC

NP-MRD ID

NP0278654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione

Description

Isomaistemonine belongs to the class of organic compounds known as azepanes. These are organic compounds containing a saturated seven member heterocycle, with one nitrogen atom. (1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione is found in Stemona japonica and Stemona kerrii. It was first documented in 2008 (PMID: 18421751). Based on a literature review a small amount of articles have been published on Isomaistemonine (PMID: 26882674) (PMID: 25632473) (PMID: 22084978).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092205452D          

 30 34  0  0  1  0            999 V2000
    1.0633    0.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7614    1.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5702    0.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3508    1.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7648    1.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8460    0.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7088    0.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3715   -0.2282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770   -0.1020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5958   -0.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -1.5612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8152   -1.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5708   -1.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3200   -0.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4965   -0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0559    0.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788    0.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992    1.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5627    1.0490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2441    1.5142    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2683    2.3388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6154    2.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8933    3.6199    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4282    4.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7179    3.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2222    4.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9497    2.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8970    1.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192    0.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7945    0.2573    0.0000 C   0  0  2  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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 27  1  6  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 19  1  6  0  0  0
  9 30  1  0  0  0  0
M  END

     RDKit          3D

 59 63  0  0  0  0  0  0  0  0999 V2000
   -1.8621   -3.4917    0.9010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7063   -2.1196    0.7970 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6502   -1.3438   -0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5092   -1.8331   -1.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3798   -3.2370   -2.0239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5123   -0.7025   -2.5106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3982   -0.7765   -3.7686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6622    0.4599   -1.7907 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7277    0.0731   -0.4331 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9936    0.6393    0.2042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9584    0.0714    0.7187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7281    2.0611    0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7861    3.1147   -0.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3986    2.2781    0.0696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9122    3.6657   -0.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1147    4.0649    0.8834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1408    2.9989    1.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2312    2.1589   -0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971    0.8399    0.0023 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3086    0.2488    1.0911 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0755   -0.9879    0.8225 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2135   -0.8434   -0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5151   -2.2907   -0.4848 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0350   -2.4518   -1.8924 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2416   -2.9950   -0.2528 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0095   -4.1854   -0.5557 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3513   -2.0938    0.3626 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3489    0.0032    2.2230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9318    0.6120    1.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7829    0.9571    0.3198 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0967   -4.1079    0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7967   -3.7329    2.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9072   -3.7858    0.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3666   -3.6100   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2043   -3.8886   -1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4472   -3.2986   -3.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6359    3.9179    0.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8054    3.4988   -1.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7682    2.6635    0.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7522    4.4039    0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5935    3.8554   -1.1733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4085    4.3001    1.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5989    5.0106    0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8948    2.4593    1.9732 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1157    3.5201    1.2642 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9813    2.6252   -1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    1.8901   -0.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0650    1.0001    1.5270 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5499   -1.3028    1.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1353   -0.4356    0.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9256   -0.2937   -1.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2665   -2.6855    0.2474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8294   -1.5908   -2.5349 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1520   -2.5639   -1.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6539   -3.3999   -2.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2602   -1.1137    2.3441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7250    0.4066    3.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -0.1356    1.9741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2378    1.4989    2.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  8  1  0
  9  8  1  6
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 28  1  0
 28 29  1  0
 30 29  1  1
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 25 27  1  0
  9  3  1  0
 30  9  1  0
 27 21  1  0
 30 14  1  0
 30 19  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  5 34  1  0
  5 35  1  0
  5 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 17 45  1  0
 18 46  1  0
 18 47  1  0
 20 48  1  1
 28 56  1  0
 28 57  1  0
 29 58  1  0
 29 59  1  0
 21 49  1  1
 22 50  1  0
 22 51  1  0
 23 52  1  1
 24 53  1  0
 24 54  1  0
 24 55  1  0
M  END


  Mrv1652309092205452D          

 30 34  0  0  1  0            999 V2000
    1.0633    0.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7614    1.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5702    0.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3508    1.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7648    1.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8460    0.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7088    0.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3715   -0.2282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5770   -0.1020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5958   -0.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0375   -1.5612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8152   -1.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5708   -1.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3200   -0.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4965   -0.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0559    0.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788    0.9593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7992    1.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5627    1.0490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2441    1.5142    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2683    2.3388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6154    2.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8933    3.6199    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4282    4.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7179    3.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2222    4.2486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9497    2.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8970    1.0099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192    0.2331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7945    0.2573    0.0000 C   0  0  2  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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 21 27  1  6  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 14 30  1  0  0  0  0
 30 19  1  6  0  0  0
  9 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0278654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(=O)O[C@@]11C(=O)C(C)=C2CCCCN3[C@@H](CC[C@@]123)[C@@H]1C[C@H](C)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C23H29NO6/c1-12-11-17(29-20(12)26)16-8-9-22-15(7-5-6-10-24(16)22)13(2)18(25)23(22)19(28-4)14(3)21(27)30-23/h12,16-17H,5-11H2,1-4H3/t12-,16-,17-,22-,23-/m0/s1

> <INCHI_KEY>
SKYPPFSYUDCEQR-VSWGTLQQSA-N

> <FORMULA>
C23H29NO6

> <MOLECULAR_WEIGHT>
415.486

> <EXACT_MASS>
415.199487658

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.24118476219681

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2R,11'S)-3-methoxy-4,4'-dimethyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5H-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0^{1,5}]tridecan]-4'-ene-3',5-dione

> <JCHEM_LOGP>
2.953444293333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.093683808177389

> <JCHEM_POLAR_SURFACE_AREA>
82.14

> <JCHEM_REFRACTIVITY>
108.91169999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,11'S)-3-methoxy-4,4'-dimethyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0^{1,5}]tridecan]-4'-ene-3',5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       1.985   1.626   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.288   2.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.798   1.567   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.255   2.066   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.028   3.576   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.179   0.834   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.790   0.777   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.293  -0.426   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.810  -0.190   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.846  -1.513   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.670  -2.914   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.388  -2.011   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.932  -3.534   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.464  -0.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.927  -0.872   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.104   0.271   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.147   1.791   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.492   2.541   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.917   1.958   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       4.189   2.826   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.234   4.366   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.015   5.307   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.534   6.757   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.666   8.029   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.073   6.712   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.015   7.931   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.506   5.234   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.408   1.885   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.889   0.435   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.350   0.480   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8    3   10   30                                             
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   30                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   30                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   21                                                       
CONECT   28   20   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   14   19    9                                             
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Value	Source
Maistemonine	MeSH

Chemical Formula

C₂₃H₂₉NO₆

Average Mass

415.4860 Da

Monoisotopic Mass

415.19949 Da

IUPAC Name

(1'S,2R,11'S)-3-methoxy-4,4'-dimethyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5H-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0^{1,5}]tridecan]-4'-ene-3',5-dione

Traditional Name

(1'S,2R,11'S)-3-methoxy-4,4'-dimethyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0^{1,5}]tridecan]-4'-ene-3',5-dione

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)O[C@@]11C(=O)C(C)=C2CCCCN3[C@@H](CC[C@@]123)[C@@H]1C[C@H](C)C(=O)O1

InChI Identifier

InChI=1S/C23H29NO6/c1-12-11-17(29-20(12)26)16-8-9-22-15(7-5-6-10-24(16)22)13(2)18(25)23(22)19(28-4)14(3)21(27)30-23/h12,16-17H,5-11H2,1-4H3/t12-,16-,17-,22-,23-/m0/s1

InChI Key

SKYPPFSYUDCEQR-VSWGTLQQSA-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
Stemona japonica	LOTUS Database	35616633
Stemona kerrii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azepanes. These are organic compounds containing a saturated seven member heterocycle, with one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azepanes

Sub Class

Not Available

Direct Parent

Azepanes

Alternative Parents

Substituents

Azepane
Alpha-acyloxy ketone
2-furanone
Dicarboxylic acid or derivatives
Gamma butyrolactone
N-alkylpyrrolidine
Dihydrofuran
Oxolane
Pyrrolidine
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Tertiary amine
Amino acid or derivatives
Tertiary aliphatic amine
Lactone
Ketone
Carboxylic acid ester
Azacycle
Oxacycle
Carboxylic acid derivative
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.95	ChemAxon
pKa (Strongest Basic)	9.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	82.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	108.91 m³·mol⁻¹	ChemAxon
Polarizability	43.24 Å³	ChemAxon
Number of Rings	5	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

C00028402

Chemspider ID

74159772

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101546109

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yi M, xia X, Wu HY, Tian HY, Huang C, But PP, Shaw PC, Jiang RW: Structures and Chemotaxonomic Significance of Stemona Alkaloids from Stemona japonica. Nat Prod Commun. 2015 Dec;10(12):2097-9. [PubMed:26882674 ]
Guo A, Jin L, Deng Z, Cai S, Guo S, Lin W: New stemona alkaloids from the roots of Stemona sessilifolia. Chem Biodivers. 2008 Apr;5(4):598-605. doi: 10.1002/cbdv.200890056. [PubMed:18421751 ]
Quang DN, Khamko VA, Trang NT, Yen LT, Dien PH: Stemofurans X-Y from the roots of Stemona species from Laos. Nat Prod Commun. 2014 Dec;9(12):1741-2. [PubMed:25632473 ]
Chen ZH, Chen ZM, Zhang YQ, Tu YQ, Zhang FM: Total synthesis of (+/-)-maistemonine, (+/-)-stemonamide, and (+/-)-isomaistemonine. J Org Chem. 2011 Dec 16;76(24):10173-86. doi: 10.1021/jo202042x. Epub 2011 Nov 23. [PubMed:22084978 ]
LOTUS database [Link]

Showing NP-Card for (1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione (NP0278654)

MOL for NP0278654 ((1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione)

3D MOL for NP0278654 ((1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione)

3D SDF for NP0278654 ((1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione)

3D-SDF for NP0278654 ((1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione)

PDB for NP0278654 ((1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione)

3D PDB for NP0278654 ((1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione)

SMILES for NP0278654 ((1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione)

INCHI for NP0278654 ((1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione)

Structure for NP0278654 ((1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione)

3D Structure for NP0278654 ((1's,2r,11's)-3-methoxy-4,4'-dimethyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-10'-azaspiro[furan-2,2'-tricyclo[8.3.0.0¹,⁵]tridecan]-4'-ene-3',5-dione)