NP-MRD: Showing NP-Card for 5-[(1s,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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 (NP0254734)

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Record Information

Version

2.0

Created at

2022-09-07 18:59:21 UTC

Updated at

2022-09-07 18:59:22 UTC

NP-MRD ID

NP0254734

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(1s,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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

5-[(1S,3Z,4S,5R,8S,9S,13R)-9-[(2S)-2-hydroxybutyl]-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]Tetradecan-3-ylidene]-4-methoxy-3-methyl-2,5-dihydrofuran-2-one 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,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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 cochinchinensis. Based on a literature review very few articles have been published on 5-[(1S,3Z,4S,5R,8S,9S,13R)-9-[(2S)-2-hydroxybutyl]-4-methyl-2,14-dioxa-10-azapentacyclo[6.5.1.0¹,⁵.0⁶,¹⁰.0⁹,¹³]Tetradecan-3-ylidene]-4-methoxy-3-methyl-2,5-dihydrofuran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072220592D          

 29 34  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  2  0  0  0  0  0  0  0  0  0
    0.5302    2.1990    0.0000 O   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  0  0  0  0  0  0  0  0  0  0
    2.8835    0.8783    0.0000 C   0  0  1  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
    3.3970   -1.1642    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 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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7162   -0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4528   -0.5892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4993    0.2345    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  6  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 23  1  0  0  0  0
 24 23  1  6  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 25  1  1  0  0  0
 24 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 29  1  0  0  0  0
  6 29  1  0  0  0  0
M  END

     RDKit          3D

 58 63  0  0  0  0  0  0  0  0999 V2000
    6.1962   -0.1325   -1.3865 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9462    0.0938   -0.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5170   -1.1988    0.1030 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2354   -2.1847   -0.8407 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4550   -1.0251    1.1187 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1813   -0.4548    0.6932 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4167   -1.1801   -0.3519 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0983   -0.0854   -1.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9256    1.0982   -0.4279 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1945    0.8645    0.5215 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5701    0.8204   -0.0260 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1657    2.2074    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2216   -0.1614    0.8833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4862   -0.5932    0.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0877   -1.5200    1.7565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4215   -1.6744    1.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3046   -2.4049    1.9193 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6761   -0.8060    0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9398   -0.6022   -0.4974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5246   -0.1760   -0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3266    0.7469   -1.0580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2965    0.2415   -2.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2575   -0.6200    1.8155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0591   -0.5187    1.1105 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1473   -1.5090    0.1802 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2054   -0.5433    1.8880 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5143    0.7265    2.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1017    1.6645    1.5973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1674    0.9339    0.3570 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1990    0.5342   -2.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2596   -1.2057   -1.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0911    0.0823   -0.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1843    0.5017   -1.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2075    0.8666    0.1918 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4348   -1.5736    0.6488 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3008   -1.8081   -1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2735   -2.0181    1.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8715   -0.3897    1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9031   -2.0405   -0.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1607   -0.2916   -1.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9454    0.1438   -2.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8933    2.0545   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1470    1.6010    1.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6160    0.4657   -1.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4141    2.9146    0.5767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0059    2.1996    0.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4104    2.6765   -0.8547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9773    0.3911   -0.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8201   -0.6629    0.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0938   -1.4387   -1.2332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1302    1.0967   -3.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2494   -0.2231   -2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5028   -0.5307   -2.5179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3785   -1.4571    2.4729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2676    0.4537    3.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6560    1.1431    3.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6037    2.6303    1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1608    1.8771    1.9181 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
  3  5  1  0
  6  5  1  1
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 23  1  0
 24 23  1  1
 24 25  1  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  1  0
 26  6  1  0
 20 14  1  0
 29  6  1  0
 25  7  1  0
 29  9  1  0
 24 10  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  1
  4 36  1  0
  5 37  1  0
  5 38  1  0
  7 39  1  6
  8 40  1  0
  8 41  1  0
  9 42  1  6
 10 43  1  1
 11 44  1  6
 12 45  1  0
 12 46  1  0
 12 47  1  0
 26 54  1  1
 27 55  1  0
 27 56  1  0
 28 57  1  0
 28 58  1  0
 19 48  1  0
 19 49  1  0
 19 50  1  0
 22 51  1  0
 22 52  1  0
 22 53  1  0
M  END


  Mrv1652309072220592D          

 29 34  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  2  0  0  0  0  0  0  0  0  0
    0.5302    2.1990    0.0000 O   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  0  0  0  0  0  0  0  0  0  0
    2.8835    0.8783    0.0000 C   0  0  1  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
    3.3970   -1.1642    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 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 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7162   -0.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4528   -0.5892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4993    0.2345    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  6  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  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
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 23  1  0  0  0  0
 24 23  1  6  0  0  0
 10 24  1  0  0  0  0
 24 25  1  0  0  0  0
  7 25  1  1  0  0  0
 24 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 29  1  0  0  0  0
  6 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0254734

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H](O)C[C@@]12[C@@H]3CC4[C@H]5[C@H](C)\C(O[C@]5(O3)[C@@H]1CCN24)=C1\OC(=O)C(C)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C22H29NO6/c1-5-12(24)9-21-14-6-7-23(21)13-8-15(21)28-22(14)16(13)10(2)18(29-22)19-17(26-4)11(3)20(25)27-19/h10,12-16,24H,5-9H2,1-4H3/b19-18-/t10-,12-,13?,14+,15-,16+,21-,22+/m0/s1

> <INCHI_KEY>
WXCVDEUJZBRYIT-WOOIFVOZSA-N

> <FORMULA>
C22H29NO6

> <MOLECULAR_WEIGHT>
403.475

> <EXACT_MASS>
403.199487658

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.83626168434529

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(1S,3Z,4S,5R,8S,9S,13R)-9-[(2S)-2-hydroxybutyl]-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>
1.0283798033333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.205596669952598

> <JCHEM_PKA_STRONGEST_BASIC>
9.747439522782138

> <JCHEM_POLAR_SURFACE_AREA>
77.46000000000001

> <JCHEM_REFRACTIVITY>
105.83539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-[(1S,3Z,4S,5R,8S,9S,13R)-9-[(2S)-2-hydroxybutyl]-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                                 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      -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  O   UNK     0       0.990   4.105   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.728   1.541   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.208   1.968   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.015  -0.003   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.953   0.629   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.481   1.212   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.382   1.640   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.378   1.853   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.476   2.933   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.200   0.433   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.434  -1.089   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.341  -2.173   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.035  -3.548   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.330  -4.918   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.557  -3.313   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.641  -4.407   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.804  -1.793   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.179  -1.100   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.265   0.438   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.440   2.086   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.391   0.579   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.431  -0.687   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.853   2.384   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.787   3.927   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.268   4.267   0.000  0.00  0.00           C+0
HETATM   29  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    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   26   29                                             
CONECT    7    6    8   25                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   29                                                  
CONECT   10    9   11   24                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   23                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   13   24                                                       
CONECT   24   23   10   25   26                                             
CONECT   25   24    7                                                       
CONECT   26   24    6   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    9    6                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₉NO₆

Average Mass

403.4750 Da

Monoisotopic Mass

403.19949 Da

IUPAC Name

5-[(1S,3Z,4S,5R,8S,9S,13R)-9-[(2S)-2-hydroxybutyl]-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,3Z,4S,5R,8S,9S,13R)-9-[(2S)-2-hydroxybutyl]-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

CC[C@H](O)C[C@@]12[C@@H]3CC4[C@H]5[C@H](C)\C(O[C@]5(O3)[C@@H]1CCN24)=C1\OC(=O)C(C)=C1OC

InChI Identifier

InChI=1S/C22H29NO6/c1-5-12(24)9-21-14-6-7-23(21)13-8-15(21)28-22(14)16(13)10(2)18(29-22)19-17(26-4)11(3)20(25)27-19/h10,12-16,24H,5-9H2,1-4H3/b19-18-/t10-,12-,13?,14+,15-,16+,21-,22+/m0/s1

InChI Key

WXCVDEUJZBRYIT-WOOIFVOZSA-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 cochinchinensis	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
1,3-aminoalcohol
Tertiary aliphatic amine
Tertiary amine
Secondary alcohol
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
Alcohol
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	1.03	ChemAxon
pKa (Strongest Acidic)	15.21	ChemAxon
pKa (Strongest Basic)	9.75	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	105.84 m³·mol⁻¹	ChemAxon
Polarizability	43.84 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

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

163193715

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[(1s,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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 (NP0254734)

MOL for NP0254734 (5-[(1s,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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 NP0254734 (5-[(1s,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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 NP0254734 (5-[(1s,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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 NP0254734 (5-[(1s,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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 NP0254734 (5-[(1s,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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 NP0254734 (5-[(1s,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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 NP0254734 (5-[(1s,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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 NP0254734 (5-[(1s,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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 NP0254734 (5-[(1s,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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 NP0254734 (5-[(1s,3z,4s,5r,8s,9s,13r)-9-[(2s)-2-hydroxybutyl]-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)