NP-MRD: Showing NP-Card for (1'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione (NP0242381)

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Record Information

Version

2.0

Created at

2022-09-07 02:41:31 UTC

Updated at

2022-09-07 02:41:31 UTC

NP-MRD ID

NP0242381

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione

Description

(1'R,2R,2'R,3'S,6'S,11'S)-3'-ethyl-4-methyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5H-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]Tridecane]-5,7'-dione 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'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione is found in Stemona tuberosa. Based on a literature review very few articles have been published on (1'R,2R,2'R,3'S,6'S,11'S)-3'-ethyl-4-methyl-11'-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-5H-5'-oxa-10'-azaspiro[furan-2,4'-tricyclo[8.3.0.0²,⁶]Tridecane]-5,7'-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072204412D          

 29 33  0  0  1  0            999 V2000
    4.8076    1.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387    0.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2224   -0.0743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6076   -0.6244    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9409   -1.3791    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7616   -1.2954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356   -0.4890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1096    0.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9304    0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3451    1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2636   -0.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0700   -0.5275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6488   -0.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5586   -2.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0514   -2.7718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7487   -2.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1210   -1.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -0.9072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750   -0.4303    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6935   -0.6945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4479   -1.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3770   -1.4919    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8540   -2.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6413   -0.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0203   -0.2176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7206    0.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8098   -0.4144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  1  0  0  0
  3  7  1  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
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 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  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 20 26  1  6  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  4 29  1  0  0  0  0
 29 18  1  6  0  0  0
M  END

     RDKit          3D

 58 62  0  0  0  0  0  0  0  0999 V2000
   -2.1790    1.0811   -1.8537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3724   -0.3146   -1.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2559   -0.5661    0.0685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9889   -0.2390    0.7441 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4897   -0.2974    2.2035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8042    0.0597    2.1928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2413    0.2387    0.8864 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6336   -0.2178    0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3346    0.8333    0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7944    0.9005   -0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670    2.0022    0.2266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8111    3.1720   -0.1099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2016    1.5983    0.5860 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5978    0.5584    2.9890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0755    1.5542    3.4667 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8325    0.3298    3.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5615    0.3020    1.9066 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -0.8700    1.1686 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4029   -1.2823    0.2843 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0051   -0.1798   -0.5491 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1391   -0.6467   -1.4021 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8999    0.6406   -1.6657 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3829    0.4694   -1.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3477    1.6038   -0.6794 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5755    2.8450   -0.7207 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5926    0.8528    0.2081 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7891   -2.3593   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3781   -1.7502   -0.7535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1134   -1.2180    0.6494 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0977    1.5352   -2.2714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6510    1.7438   -1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750    1.0515   -2.7416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4562   -0.5713   -1.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8036   -1.0244   -1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5232   -1.6364    0.2305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6988    0.8145    0.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3412   -1.3587    2.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9830   -1.2091    0.8411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3383    0.0735    0.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8816    0.8769   -1.1138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2544    1.8452    0.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9320   -0.6694    3.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2848    1.0909    3.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6488    0.2950    2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4269    1.2534    1.3835 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2137   -1.7593    0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2585    0.2998   -1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7916   -1.0305   -2.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8317   -1.3351   -0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8010    0.9878   -2.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5649    0.4360   -0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0115    1.1676   -1.8835 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6446   -0.5596   -1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2433   -2.4277   -1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7156   -3.3074   -0.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717   -2.5872   -1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -0.9580   -1.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2375   -2.1373    1.2154 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 29  1  0
 29 28  1  0
 28 27  1  0
 27 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 14  5  1  0
  5  6  1  0
  7  6  1  1
  7 13  1  0
 13 11  1  0
 11 12  2  0
 11  9  1  0
  9 10  1  0
  9  8  2  0
  7  3  1  0
  8  7  1  0
  5  4  1  0
 18 29  1  0
 26 20  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  2 34  1  0
  3 35  1  6
  4 36  1  6
 29 58  1  1
 28 56  1  0
 28 57  1  0
 27 54  1  0
 27 55  1  0
 19 46  1  1
 20 47  1  6
 21 48  1  0
 21 49  1  0
 22 50  1  6
 23 51  1  0
 23 52  1  0
 23 53  1  0
 17 44  1  0
 17 45  1  0
 16 42  1  0
 16 43  1  0
  5 37  1  1
 10 39  1  0
 10 40  1  0
 10 41  1  0
  8 38  1  0
M  END


  Mrv1652309072204412D          

 29 33  0  0  1  0            999 V2000
    4.8076    1.2293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1387    0.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2224   -0.0743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6076   -0.6244    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9409   -1.3791    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7616   -1.2954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9356   -0.4890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1096    0.3175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9304    0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3451    1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2636   -0.3535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0700   -0.5275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6488   -0.9037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5586   -2.1102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0514   -2.7718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7487   -2.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1210   -1.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -0.9072    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750   -0.4303    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6935   -0.6945    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4479   -1.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3770   -1.4919    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8540   -2.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6413   -0.7104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0203   -0.2176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7206    0.3573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5456    0.3671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8098   -0.4144    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  1  0  0  0
  3  7  1  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
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 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  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 20 26  1  6  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  4 29  1  0  0  0  0
 29 18  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0242381

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1[C@@H]2[C@H]3CC[C@@H]([C@@H]4C[C@H](C)C(=O)O4)N3CCC(=O)[C@H]2O[C@@]11OC(=O)C(C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H29NO6/c1-4-13-18-15-6-5-14(17-9-11(2)20(25)27-17)23(15)8-7-16(24)19(18)28-22(13)10-12(3)21(26)29-22/h10-11,13-15,17-19H,4-9H2,1-3H3/t11-,13-,14-,15+,17-,18+,19+,22-/m0/s1

> <INCHI_KEY>
POQHFALZNYMCBA-CWHSMJNRSA-N

> <FORMULA>
C22H29NO6

> <MOLECULAR_WEIGHT>
403.475

> <EXACT_MASS>
403.199487658

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.73148421528985

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,2R,2'R,3'S,6'S,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]-5,7'-dione

> <JCHEM_LOGP>
3.2889795009999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.915032646312376

> <JCHEM_PKA_STRONGEST_BASIC>
10.245581639130062

> <JCHEM_POLAR_SURFACE_AREA>
82.14

> <JCHEM_REFRACTIVITY>
103.17679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2R,2'R,3'S,6'S,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]-5,7'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       8.974   2.295   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.726   1.393   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.882  -0.139   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.734  -1.166   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.356  -2.574   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.888  -2.418   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.213  -0.913   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.538   0.593   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.070   0.749   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.844   2.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.692  -0.660   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.197  -0.985   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      10.544  -1.687   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.643  -3.939   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.563  -5.174   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.131  -4.232   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.959  -3.233   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.010  -1.693   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0       2.753  -0.803   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.295  -1.296   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.836  -2.767   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.704  -2.785   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.594  -4.041   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.197  -1.326   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.667  -0.868   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.038  -0.406   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.212   0.667   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.752   0.685   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.245  -0.774   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5   29                                                  
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    3    8   13                                             
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7                                                       
CONECT   14    5   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20   27                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   20                                                       
CONECT   27   19   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    4   18                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₉NO₆

Average Mass

403.4750 Da

Monoisotopic Mass

403.19949 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC[C@H]1[C@@H]2[C@H]3CC[C@@H]([C@@H]4C[C@H](C)C(=O)O4)N3CCC(=O)[C@H]2O[C@@]11OC(=O)C(C)=C1

InChI Identifier

InChI=1S/C22H29NO6/c1-4-13-18-15-6-5-14(17-9-11(2)20(25)27-17)23(15)8-7-16(24)19(18)28-22(13)10-12(3)21(26)29-22/h10-11,13-15,17-19H,4-9H2,1-3H3/t11-,13-,14-,15+,17-,18+,19+,22-/m0/s1

InChI Key

POQHFALZNYMCBA-CWHSMJNRSA-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 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
Ketone
Lactone
Tertiary amine
Tertiary aliphatic amine
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organooxygen compound
Organic nitrogen compound
Organic oxygen 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

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

163191270

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione (NP0242381)

MOL for NP0242381 ((1'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione)

3D MOL for NP0242381 ((1'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione)

3D SDF for NP0242381 ((1'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione)

3D-SDF for NP0242381 ((1'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione)

PDB for NP0242381 ((1'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione)

3D PDB for NP0242381 ((1'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione)

SMILES for NP0242381 ((1'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione)

INCHI for NP0242381 ((1'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione)

Structure for NP0242381 ((1'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione)

3D Structure for NP0242381 ((1'r,2r,2'r,3's,6's,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]tridecane]-5,7'-dione)