NP-MRD: Showing NP-Card for 5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one (NP0185379)

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Record Information

Version

2.0

Created at

2022-09-04 00:45:56 UTC

Updated at

2022-09-04 00:45:56 UTC

NP-MRD ID

NP0185379

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

Description

Isostemofoline belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. 5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one is found in Stemona japonica. 5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one was first documented in 2009 (PMID: 19183047). Based on a literature review a small amount of articles have been published on Isostemofoline (PMID: 33082332) (PMID: 28899501).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202452D          

 28 33  0  0  1  0            999 V2000
   -1.0554    1.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613    1.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315    1.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9256    0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7184    1.0541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6151   -0.0014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0465    0.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8648    0.6494    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8835    0.8783    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9523    0.9929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5408    1.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8569    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -0.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7162   -0.9607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5839   -1.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1649   -2.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7685   -1.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3910   -2.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3970   -1.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5826   -1.0319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0609   -1.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    1.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879    0.3103    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3735   -0.3683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000    1.2771    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5644    2.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7507    2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3795    1.4923    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
  9  8  1  6  0  0  0
  9 10  1  0  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
 17 18  1  0  0  0  0
 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
 12 22  1  0  0  0  0
 23 22  1  6  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  1  0  0  0
 23 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  6  0  0  0
  5 28  1  0  0  0  0
M  END

     RDKit          3D

 57 62  0  0  0  0  0  0  0  0999 V2000
    5.4365   -0.0134    0.9133 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5802    0.7444   -0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4882    1.6976   -0.7164 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1443    1.2792   -0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1754    0.6188   -0.1391 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7145    1.2157    1.1221 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9167    0.0553    2.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3853   -1.0950    1.1751 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0288   -0.7580    1.0757 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1277   -1.6549    0.8107 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1647   -2.6596   -0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1653   -0.6029    0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4684   -0.7537    0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1445   -1.8748    1.1433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5068   -1.6071    1.1401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4629   -2.3476    1.5260 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6899   -0.2675    0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0009    0.4245    0.4101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5047    0.2277    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2002    1.4689   -0.2501 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1880    1.5655   -1.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4910    0.4988   -0.0607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1194    0.4610    0.1881 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3373    1.5185    0.9828 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7981    0.5593   -0.9100 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0494   -0.5141   -1.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0376   -1.4171   -1.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2693   -0.8045    0.0842 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8464   -0.9303    0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0695    0.6628    1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4434   -0.3364    1.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7925    0.0251   -1.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5800    1.2861   -0.2768 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8680    2.2306   -1.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6193    2.5397    0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2153    0.6215   -1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5590    2.1624   -1.4589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1713    2.1358    1.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9510   -0.0493    2.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2364    0.1435    2.9643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5562   -2.0485    1.6611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3421   -0.3600    2.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -2.1756    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2621   -3.2667   -0.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296   -2.2657   -1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9828   -3.4110    0.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2149    1.1373    1.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0286    0.9839   -0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8417   -0.3010    0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    0.8430   -2.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0070    2.5879   -2.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1516    1.2184   -2.1147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7446    1.5592   -1.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375   -0.0645   -2.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1857   -1.0427   -2.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254   -1.3797   -1.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7920   -2.4739   -1.1713 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  6
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 22  1  0
 23 22  1  6
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 25  5  1  0
 19 13  1  0
 28  5  1  0
 24  6  1  0
 28  8  1  0
 23  9  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  0
  3 35  1  0
  4 36  1  0
  4 37  1  0
  6 38  1  1
  7 39  1  0
  7 40  1  0
  8 41  1  1
  9 42  1  1
 10 43  1  1
 11 44  1  0
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 11 46  1  0
 25 53  1  6
 26 54  1  0
 26 55  1  0
 27 56  1  0
 27 57  1  0
 18 47  1  0
 18 48  1  0
 18 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
M  END


  Mrv1652309042202452D          

 28 33  0  0  1  0            999 V2000
   -1.0554    1.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4613    1.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315    1.3983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9256    0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7184    1.0541    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6151   -0.0014    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0465    0.3371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8648    0.6494    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8835    0.8783    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9523    0.9929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5408    1.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8569    0.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -0.5832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7162   -0.9607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5839   -1.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1649   -2.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7685   -1.9008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3910   -2.6344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3970   -1.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5826   -1.0319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0609   -1.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4499    1.1177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8879    0.3103    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3735   -0.3683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000    1.2771    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5644    2.1038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7507    2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3795    1.4923    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
  9  8  1  6  0  0  0
  9 10  1  0  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
 17 18  1  0  0  0  0
 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
 12 22  1  0  0  0  0
 23 22  1  6  0  0  0
  9 23  1  0  0  0  0
 23 24  1  0  0  0  0
  6 24  1  1  0  0  0
 23 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  6  0  0  0
  5 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0185379

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC[C@@]12[C@@H]3C[C@H]4[C@@H]5[C@H](C)\C(O[C@]5(O3)[C@@H]1CCN24)=C1/OC(=O)C(C)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H29NO5/c1-5-6-8-21-14-7-9-23(21)13-10-15(21)27-22(14)16(13)11(2)18(28-22)19-17(25-4)12(3)20(24)26-19/h11,13-16H,5-10H2,1-4H3/b19-18+/t11-,13-,14+,15-,16-,21-,22+/m0/s1

> <INCHI_KEY>
DTVYAHOULQCSMS-KDRVYIRMSA-N

> <FORMULA>
C22H29NO5

> <MOLECULAR_WEIGHT>
387.476

> <EXACT_MASS>
387.204573038

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.121675319511894

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(1S,3E,4S,5S,6S,8S,9S,13R)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0^{1,5}.0^{6,10}.0^{9,13}]tetradecan-3-ylidene]-4-methoxy-3-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
2.4878923363333323

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
10.14374932240474

> <JCHEM_POLAR_SURFACE_AREA>
57.23000000000001

> <JCHEM_REFRACTIVITY>
104.20949999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1S,3E,4S,5S,6S,8S,9S,13R)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0^{1,5}.0^{6,10}.0^{9,13}]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.970   3.253   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.861   2.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.619   2.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.728   1.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.208   1.968   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.015  -0.003   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.953   0.629   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.481   1.212   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.382   1.640   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.378   1.853   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.476   2.933   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.200   0.433   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.434  -1.089   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.804  -1.793   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.557  -3.313   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.641  -4.407   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.035  -3.548   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.330  -4.918   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.341  -2.173   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.821  -1.926   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.847  -3.119   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.440   2.086   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.391   0.579   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.431  -0.687   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.853   2.384   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.787   3.927   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.268   4.267   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0       2.575   2.786   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   23                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   22                                                  
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   12   23                                                       
CONECT   23   22    9   24   25                                             
CONECT   24   23    6                                                       
CONECT   25   23    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   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₉NO₅

Average Mass

387.4760 Da

Monoisotopic Mass

387.20457 Da

IUPAC Name

5-[(1S,3E,4S,5S,6S,8S,9S,13R)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0^{1,5}.0^{6,10}.0^{9,13}]tetradecan-3-ylidene]-4-methoxy-3-methyl-2,5-dihydrofuran-2-one

Traditional Name

5-[(1S,3E,4S,5S,6S,8S,9S,13R)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0^{1,5}.0^{6,10}.0^{9,13}]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one

CAS Registry Number

Not Available

SMILES

CCCC[C@@]12[C@@H]3C[C@H]4[C@@H]5[C@H](C)\C(O[C@]5(O3)[C@@H]1CCN24)=C1/OC(=O)C(C)=C1OC

InChI Identifier

InChI=1S/C22H29NO5/c1-5-6-8-21-14-7-9-23(21)13-10-15(21)27-22(14)16(13)11(2)18(28-22)19-17(25-4)12(3)20(24)26-19/h11,13-16H,5-10H2,1-4H3/b19-18+/t11-,13-,14+,15-,16-,21-,22+/m0/s1

InChI Key

DTVYAHOULQCSMS-KDRVYIRMSA-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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Aminoglycoside core
Stemoamide backbone
Stemona alkaloid
Furopyran
Pyrrolizidine
Ketal
Azepane
Para-oxazepine
N-alkylpyrrolidine
Pyran
Piperidine
Oxane
2-furanone
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Pyrrolidine
Furan
Enol ester
Dihydrofuran
Tertiary aliphatic amine
Tertiary amine
Lactone
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Carbonyl group
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	2.49	ChemAxon
pKa (Strongest Basic)	10.14	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	57.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.21 m³·mol⁻¹	ChemAxon
Polarizability	42.12 Å³	ChemAxon
Number of Rings	6	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

C00039455

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

100951114

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huang XZ, Gao LH, Huang PQ: Enantioselective total syntheses of (+)-stemofoline and three congeners based on a biogenetic hypothesis. Nat Commun. 2020 Oct 20;11(1):5314. doi: 10.1038/s41467-020-19163-4. [PubMed:33082332 ]
Umsumarng S, Pitchakarn P, Yodkeeree S, Punfa W, Mapoung S, Ramli RA, Pyne SG, Limtrakul P: Modulation of P-glycoprotein by Stemona alkaloids in human multidrug resistance leukemic cells and structural relationships. Phytomedicine. 2017 Oct 15;34:182-190. doi: 10.1016/j.phymed.2017.08.004. Epub 2017 Aug 3. [PubMed:28899501 ]
Sastraruji K, Pyne SG, Ung AT, Mungkornasawakul P, Lie W, Jatisatienr A: Structural revision of stemoburkilline from an E-alkene to a Z-alkene. J Nat Prod. 2009 Feb 27;72(2):316-8. doi: 10.1021/np800755p. [PubMed:19183047 ]
LOTUS database [Link]

Showing NP-Card for 5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one (NP0185379)

MOL for NP0185379 (5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one)

3D MOL for NP0185379 (5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one)

3D SDF for NP0185379 (5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one)

3D-SDF for NP0185379 (5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one)

PDB for NP0185379 (5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one)

3D PDB for NP0185379 (5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one)

SMILES for NP0185379 (5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one)

INCHI for NP0185379 (5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one)

Structure for NP0185379 (5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one)

3D Structure for NP0185379 (5-[(1s,3e,4s,5s,6s,8s,9s,13r)-9-butyl-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]tetradecan-3-ylidene]-4-methoxy-3-methylfuran-2-one)