NP-MRD: Showing NP-Card for (5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one (NP0314425)

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Record Information

Version

2.0

Created at

2022-09-11 12:30:57 UTC

Updated at

2022-09-11 12:30:57 UTC

NP-MRD ID

NP0314425

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one

Description

(5E)-5-[(2R)-2-[(1S,2S,6R,7R,8R,9S)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]Undecan-8-yl]propylidene]-4-methoxy-3-methyl-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. (5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one is found in Stemona burkillii. Based on a literature review very few articles have been published on (5E)-5-[(2R)-2-[(1S,2S,6R,7R,8R,9S)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]Undecan-8-yl]propylidene]-4-methoxy-3-methyl-2,5-dihydrofuran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112214302D          

 28 32  0  0  1  0            999 V2000
   -1.1505    1.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9284    1.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1293    0.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1318   -0.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2060   -0.0378    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7861   -0.0077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8258   -0.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3765   -0.7673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8949   -0.1015    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7598   -0.1328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4559    0.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2822   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -1.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3854   -2.2919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8444   -2.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0304   -3.7185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0849   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779   -3.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1564   -1.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5335   -1.2299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7536   -1.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4110    0.6014    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8786    1.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9257    0.9528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3072    0.6621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4417    0.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4445   -0.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2885   -0.7894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  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  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
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 13 19  1  0  0  0  0
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  9 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  6 24  1  1  0  0  0
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  5 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8 28  1  1  0  0  0
  5 28  1  0  0  0  0
M  END

     RDKit          3D

 59 63  0  0  0  0  0  0  0  0999 V2000
    6.4848    0.9243   -1.5579 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6459    0.7311   -0.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1925    0.3894   -0.7090 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4558    0.2203    0.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0353   -0.1018    0.5446 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5721   -0.2122    2.0103 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1175   -1.6583    2.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5048   -1.7403    0.6858 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7117   -0.7689    0.4503 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8342   -1.3015    1.2407 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2173   -2.7465    0.9795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8445   -0.5368    1.9290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6798    0.3793    1.4442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6472    1.1242    2.1437 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2996    1.9432    1.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2231    2.7346    1.5925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7143    1.6986   -0.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1594    2.4054   -1.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7711    0.7814    0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0182    0.3017   -0.9313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5383   -0.6947   -1.7930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1682    0.5586    0.8637 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9512    1.6667    0.7369 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4401    0.5429    2.1429 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0765    0.8773    0.0120 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8517    0.4755   -1.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2397   -0.9629   -1.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203   -1.3018   -0.1304 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3271    1.9526   -1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5536    0.8714   -1.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3251    0.1462   -2.3053 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5818    1.7086    0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0638   -0.0062    0.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8699    1.1753   -1.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2930   -0.6072   -1.2303 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375    1.1297    1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860   -0.5962    1.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1575   -2.7544    0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1481   -3.0239    1.5143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926   -2.9560   -0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4757   -3.4952    1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405   -0.6614    3.0338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2259    2.1485   -1.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5074    2.1181   -2.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0279    3.5038   -1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4538   -0.2762   -2.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8078   -1.0571   -2.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265   -1.5049   -1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8994    2.0171   -0.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3206    1.9290    0.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1345    0.7247   -1.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5727    1.0849   -2.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1561   -1.0900   -2.1188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5099   -1.6474   -1.9318 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
  5  4  1  1
  5  6  1  0
  6  7  1  0
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 12 13  2  0
 13 14  1  0
 14 15  1  0
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  9 22  1  0
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 22 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 25  5  1  0
 28  5  1  0
 24  6  1  0
 28  8  1  0
 19 13  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
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 18 48  1  0
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 21 51  1  0
 21 52  1  0
 21 53  1  0
 23 54  1  0
 25 55  1  6
 26 56  1  0
 26 57  1  0
 27 58  1  0
 27 59  1  0
M  END


  Mrv1652309112214302D          

 28 32  0  0  1  0            999 V2000
   -1.1505    1.8845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9284    1.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1293    0.8849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1318   -0.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2060   -0.0378    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7861   -0.0077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8258   -0.9854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3765   -0.7673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8949   -0.1015    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7598   -0.1328    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4559    0.3521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2822   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -1.5849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3854   -2.2919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8444   -2.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0304   -3.7185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0849   -2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779   -3.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1564   -1.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5335   -1.2299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7536   -1.4989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4110    0.6014    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8786    1.3538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9257    0.9528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3072    0.6621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4417    0.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4445   -0.5431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2885   -0.7894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  6  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  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
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 17 19  2  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  9 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  6 24  1  1  0  0  0
 22 25  1  0  0  0  0
  5 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  8 28  1  1  0  0  0
  5 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314425

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC[C@@]12[C@@H]3C[C@H]4[C@@H]([C@H](C)\C=C5\OC(=O)C(C)=C5OC)[C@@](O)(O3)[C@@H]1CCN24

> <INCHI_IDENTIFIER>
InChI=1S/C22H31NO5/c1-5-6-8-21-16-7-9-23(21)14-11-17(21)28-22(16,25)18(14)12(2)10-15-19(26-4)13(3)20(24)27-15/h10,12,14,16-18,25H,5-9,11H2,1-4H3/b15-10+/t12-,14+,16-,17+,18-,21+,22+/m1/s1

> <INCHI_KEY>
LLRUDQNWYFSTOW-OVKNHAENSA-N

> <FORMULA>
C22H31NO5

> <MOLECULAR_WEIGHT>
389.492

> <EXACT_MASS>
389.220223102

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
42.491384410208816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-5-[(2R)-2-[(1S,2S,6R,7R,8R,9S)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0^{2,6}.0^{3,9}]undecan-8-yl]propylidene]-4-methoxy-3-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
2.4505587026105977

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.550102633191276

> <JCHEM_PKA_STRONGEST_BASIC>
9.898122211734222

> <JCHEM_POLAR_SURFACE_AREA>
68.23

> <JCHEM_REFRACTIVITY>
105.7503

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5E)-5-[(2R)-2-[(1S,2S,6R,7R,8R,9S)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0^{2,6}.0^{3,9}]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.148   3.518   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.733   2.034   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.241   1.652   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.246  -0.092   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.251  -0.071   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.334  -0.014   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.408  -1.839   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.436  -1.432   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.404  -0.190   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.018  -0.248   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.318   0.657   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.993  -1.541   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.392  -2.959   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.186  -4.278   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.176  -5.441   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.523  -6.941   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.758  -4.840   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.439  -5.634   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.892  -3.306   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.729  -2.296   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.273  -2.798   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.500   1.123   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.373   2.527   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.595   1.779   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.440   1.236   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.825   0.649   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.830  -1.014   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       2.405  -1.473   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   25   28                                             
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   28                                                  
CONECT    9    8   10   22                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22    9   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22    6                                                       
CONECT   25   22    5   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    8    5                                                  
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

(5E)-5-[(2R)-2-[(1S,2S,6R,7R,8R,9S)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0^{2,6}.0^{3,9}]undecan-8-yl]propylidene]-4-methoxy-3-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5E)-5-[(2R)-2-[(1S,2S,6R,7R,8R,9S)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0^{2,6}.0^{3,9}]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one

CAS Registry Number

Not Available

SMILES

CCCC[C@@]12[C@@H]3C[C@H]4[C@@H]([C@H](C)\C=C5\OC(=O)C(C)=C5OC)[C@@](O)(O3)[C@@H]1CCN24

InChI Identifier

InChI=1S/C22H31NO5/c1-5-6-8-21-16-7-9-23(21)14-11-17(21)28-22(16,25)18(14)12(2)10-15-19(26-4)13(3)20(24)27-15/h10,12,14,16-18,25H,5-9,11H2,1-4H3/b15-10+/t12-,14+,16-,17+,18-,21+,22+/m1/s1

InChI Key

LLRUDQNWYFSTOW-OVKNHAENSA-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 burkillii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizidines

Sub Class

Not Available

Direct Parent

Pyrrolizidines

Alternative Parents

Substituents

Pyrrolizidine
Para-oxazepine
Azepane
2-furanone
Oxane
Piperidine
N-alkylpyrrolidine
Cyclic alcohol
Dihydrofuran
Enol ester
Pyrrolidine
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Amino acid or derivatives
Tertiary aliphatic amine
Tertiary amine
Lactone
Hemiacetal
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Hydrocarbon derivative
Organic nitrogen compound
Amine
Organonitrogen compound
Organic oxygen compound
Organooxygen compound
Organic oxide
Organopnictogen compound
Carbonyl group
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	2.45	ChemAxon
pKa (Strongest Acidic)	11.55	ChemAxon
pKa (Strongest Basic)	9.9	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	105.75 m³·mol⁻¹	ChemAxon
Polarizability	42.49 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162910415

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one (NP0314425)

MOL for NP0314425 ((5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one)

3D MOL for NP0314425 ((5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one)

3D SDF for NP0314425 ((5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one)

3D-SDF for NP0314425 ((5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one)

PDB for NP0314425 ((5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one)

3D PDB for NP0314425 ((5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one)

SMILES for NP0314425 ((5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one)

INCHI for NP0314425 ((5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one)

Structure for NP0314425 ((5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one)

3D Structure for NP0314425 ((5e)-5-[(2r)-2-[(1s,2s,6r,7r,8r,9s)-2-butyl-7-hydroxy-11-oxa-3-azatetracyclo[5.3.1.0²,⁶.0³,⁹]undecan-8-yl]propylidene]-4-methoxy-3-methylfuran-2-one)