NP-MRD: Showing NP-Card for (1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one (NP0150707)

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Record Information

Version

2.0

Created at

2022-09-02 06:54:12 UTC

Updated at

2022-09-02 06:54:12 UTC

NP-MRD ID

NP0150707

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one

Description

Stemoninine belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively. (1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one is found in Stemona sessilifolia and Stemona tuberosa. (1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one was first documented in 2014 (PMID: 26027114). Based on a literature review a small amount of articles have been published on stemoninine (PMID: 35815290) (PMID: 28580601).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022208542D          

 28 32  0  0  1  0            999 V2000
    2.2558   -0.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9247   -1.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8410   -2.2133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4558   -2.7634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2536   -2.5534    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5179   -1.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3428   -1.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5884   -2.5693    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3699   -2.8335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0431   -2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7047   -2.8494    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4923   -2.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4405   -3.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9174   -4.3041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6155   -3.6211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9153   -3.0462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9425   -3.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3148   -4.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5048   -4.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1226   -3.5181    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3018   -3.4344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1278   -2.6280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4146   -3.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7998   -2.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0066   -2.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1331   -1.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7184   -1.0246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9538   -1.8215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  4  3  1  6  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  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  9 15  1  6  0  0  0
  8 16  1  0  0  0  0
  5 16  1  6  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
  4 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 21  1  1  0  0  0
  3 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
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 22 28  1  0  0  0  0
M  END

     RDKit          3D

 59 63  0  0  0  0  0  0  0  0999 V2000
    3.2859   -1.8026    2.3205 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2725   -0.6808    2.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9594   -0.2276    0.9842 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9505    0.8863    0.9485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4643    0.4950    0.8059 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8096   -0.8399    1.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1071   -1.1627    0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8026   -0.6437   -0.6990 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0463   -0.5014   -1.5222 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1111    0.3630   -0.9524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2989   -0.5497   -0.6175 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8657   -0.0886    0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6230   -1.8526   -0.5480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8572   -2.8362    0.2281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6421   -1.8106   -1.5252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9912    0.4968   -0.5363 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4902    1.7549   -0.9510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3955    2.6862   -1.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6770    2.8898   -0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4005    1.5812   -0.3228 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7560    1.7186   -0.0557 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1556    0.4249    0.3172 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6263   -0.3398   -0.8641 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9028   -0.6465   -0.7437 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7593   -1.4084   -1.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3521   -0.1035    0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5376   -0.2100    0.9721 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2805    0.5265    1.1299 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4702   -2.1603    1.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8168   -2.6843    2.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2541   -1.5440    2.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3703   -0.9454    2.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7653    0.1401    2.9732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   -1.0906    0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1644    1.5375    1.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0829    1.2555    1.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1093   -1.6435    1.1856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698   -0.6877    2.5022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9056   -0.6179    1.1990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2164   -2.2656    0.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1904   -1.4476   -1.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7655   -0.2947   -2.5529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8236    0.9639   -0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5428    1.0915   -1.7013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0929   -0.5026   -1.3650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2660   -0.4024    1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8296    1.0356    0.6857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9422   -0.3484    0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2439    1.7330   -1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8469    2.3007   -0.0282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0282    2.2905   -2.4290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8512    3.6747   -1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2983    3.7374   -0.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1029    3.1220    0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2862    0.9299   -1.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0370   -0.6273   -1.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9742   -2.4174   -1.3478 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7240   -0.8570   -1.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3146   -1.3940   -2.7337 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 20  1  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 13 15  1  0
 20 21  1  0
 22 21  1  6
 22 28  1  0
 28 26  1  0
 26 27  2  0
 26 24  1  0
 24 25  1  0
 24 23  2  0
 22  3  1  0
 23 22  1  0
  5  4  1  0
 15  9  1  0
  5 16  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  2 33  1  0
  3 34  1  6
  4 35  1  1
 20 55  1  6
 19 53  1  0
 19 54  1  0
 18 51  1  0
 18 52  1  0
 17 49  1  0
 17 50  1  0
  8 41  1  6
  7 39  1  0
  7 40  1  0
  6 37  1  0
  6 38  1  0
  5 36  1  1
  9 42  1  6
 10 43  1  0
 10 44  1  0
 11 45  1  6
 12 46  1  0
 12 47  1  0
 12 48  1  0
 25 57  1  0
 25 58  1  0
 25 59  1  0
 23 56  1  0
M  END


  Mrv1652309022208542D          

 28 32  0  0  1  0            999 V2000
    2.2558   -0.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9247   -1.3925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8410   -2.2133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4558   -2.7634    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2536   -2.5534    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5179   -1.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3428   -1.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5884   -2.5693    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3699   -2.8335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0431   -2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7047   -2.8494    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4923   -2.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4405   -3.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9174   -4.3041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6155   -3.6211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9153   -3.0462    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9425   -3.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3148   -4.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5048   -4.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1226   -3.5181    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3018   -3.4344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1278   -2.6280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4146   -3.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7998   -2.4925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0066   -2.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1331   -1.7378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7184   -1.0246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9538   -1.8215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  4  3  1  6  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  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  9 15  1  6  0  0  0
  8 16  1  0  0  0  0
  5 16  1  6  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
  4 20  1  0  0  0  0
 20 21  1  1  0  0  0
 22 21  1  1  0  0  0
  3 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
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 22 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150707

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1[C@H]2[C@@H](CCCN3[C@@H](CC[C@@H]23)[C@@H]2C[C@H](C)C(=O)O2)O[C@@]11OC(=O)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H31NO5/c1-4-14-19-16-8-7-15(18-10-12(2)20(24)26-18)23(16)9-5-6-17(19)27-22(14)11-13(3)21(25)28-22/h11-12,14-19H,4-10H2,1-3H3/t12-,14-,15-,16-,17+,18-,19+,22-/m0/s1

> <INCHI_KEY>
UINUUSQOLRQGNF-KLDYRVGWSA-N

> <FORMULA>
C22H31NO5

> <MOLECULAR_WEIGHT>
389.492

> <EXACT_MASS>
389.220223102

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
43.19691185046855

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2R,2'R,3'S,6'R,11'S)-3'-ethyl-4-methyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5H-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0^{2,6}]tridecane]-5-one

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
3.79663716

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
11.287453108853748

> <JCHEM_POLAR_SURFACE_AREA>
65.07

> <JCHEM_REFRACTIVITY>
102.8667

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2R,2'R,3'S,6'R,11'S)-3'-ethyl-4-methyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0^{2,6}]tridecane]-5-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.211  -1.698   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.460  -2.599   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.303  -4.131   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.451  -5.158   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.940  -4.766   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.433  -3.307   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.973  -3.326   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.432  -4.796   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.891  -5.289   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.147  -4.399   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.382  -5.319   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.852  -4.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.889  -6.778   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.779  -8.034   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      12.349  -6.759   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0       9.175  -5.686   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       9.226  -7.225   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.054  -8.225   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.542  -7.932   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.829  -6.567   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.297  -6.411   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.972  -4.906   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.641  -5.680   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.493  -4.653   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.012  -4.978   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.115  -3.244   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.341  -1.913   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       3.647  -3.400   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    9                                                       
CONECT   16    8    5   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    4   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21    3   23   28                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   22                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₁NO₅

Average Mass

389.4920 Da

Monoisotopic Mass

389.22022 Da

IUPAC Name

(1'S,2R,2'R,3'S,6'R,11'S)-3'-ethyl-4-methyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5H-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0^{2,6}]tridecane]-5-one

Traditional Name

(1'S,2R,2'R,3'S,6'R,11'S)-3'-ethyl-4-methyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0^{2,6}]tridecane]-5-one

CAS Registry Number

Not Available

SMILES

CC[C@H]1[C@H]2[C@@H](CCCN3[C@@H](CC[C@@H]23)[C@@H]2C[C@H](C)C(=O)O2)O[C@@]11OC(=O)C(C)=C1

InChI Identifier

InChI=1S/C22H31NO5/c1-4-14-19-16-8-7-15(18-10-12(2)20(24)26-18)23(16)9-5-6-17(19)27-22(14)11-13(3)21(25)28-22/h11-12,14-19H,4-10H2,1-3H3/t12-,14-,15-,16-,17+,18-,19+,22-/m0/s1

InChI Key

UINUUSQOLRQGNF-KLDYRVGWSA-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 sessilifolia	LOTUS Database	35616633
Stemona tuberosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stichoneurine-type alkaloids. These are stemona alkaloids with a structure that typically contains a 3-methyloxolan-2-one and a 5-propyloxolan-2-one moieties that are attached to the characteristic pyrrolo[1,2-a]azepine skeleton at the C3 and C9 position, respectively.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Stemona alkaloids

Sub Class

Stemoamide-type alkaloids

Direct Parent

Stichoneurine-type alkaloids

Alternative Parents

Substituents

Stichoneurine-type alkaloid
Azepane
Ketal
2-furanone
Dicarboxylic acid or derivatives
Gamma butyrolactone
N-alkylpyrrolidine
Dihydrofuran
Pyrrolidine
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Oxacycle
Acetal
Azacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
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	2.46	ALOGPS
logP	3.8	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	11.29	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	102.87 m³·mol⁻¹	ChemAxon
Polarizability	43.2 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

C00029049

Chemspider ID

13115368

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15983991

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liao JN, Qin SD, Qu XS, Lin K, Huang DP, Li FX, Fan LL: [Comparative study of four alkaloids contents and antitussive activities of Stemona tuberosa from different habitats of Guangxi Province]. Zhong Yao Cai. 2014 Nov;37(11):1956-60. [PubMed:26027114 ]
Guo DH, Hao JP, Li XJ, Miao Q, Zhang Q: Exploration in the Mechanism of Zhisou San for the Treatment of Cough Variant Asthma Based on Network Pharmacology. Evid Based Complement Alternat Med. 2022 Jun 29;2022:1698571. doi: 10.1155/2022/1698571. eCollection 2022. [PubMed:35815290 ]
Chen G, Brecker L, Felsinger S, Cai XH, Kongkiatpaiboon S, Schinnerl J: Morphological and chemical variation of Stemona tuberosa from southern China - Evidence for heterogeneity of this medicinal plant species. Plant Biol (Stuttg). 2017 Sep;19(5):835-842. doi: 10.1111/plb.12587. Epub 2017 Jun 28. [PubMed:28580601 ]
LOTUS database [Link]

Showing NP-Card for (1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one (NP0150707)

MOL for NP0150707 ((1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one)

3D MOL for NP0150707 ((1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one)

3D SDF for NP0150707 ((1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one)

3D-SDF for NP0150707 ((1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one)

PDB for NP0150707 ((1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one)

3D PDB for NP0150707 ((1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one)

SMILES for NP0150707 ((1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one)

INCHI for NP0150707 ((1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one)

Structure for NP0150707 ((1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one)

3D Structure for NP0150707 ((1's,2r,2'r,3's,6'r,11's)-3'-ethyl-4-methyl-11'-[(2s,4s)-4-methyl-5-oxooxolan-2-yl]-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]tridecan]-5-one)