NP-MRD: Showing NP-Card for stemona-lactam Q (NP0042548)

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Record Information

Version

1.0

Created at

2021-06-21 00:10:50 UTC

Updated at

2021-06-30 00:17:41 UTC

NP-MRD ID

NP0042548

Secondary Accession Numbers

None

Natural Product Identification

Common Name

stemona-lactam Q

Provided By

JEOL Database JEOL Logo

Description

stemona-lactam Q is found in Stemona tuberosa. It was first documented in 2013 (Hitotsuyanagi, Y., et al.). Based on a literature review very few articles have been published on (alphaS)-alpha-Methyl-1-oxo-3alpha-(4alpha-methyl-5-oxotetrahydrofuran-2alpha-yl)-4aalpha,6beta-dihydroxy-7alpha-ethyl-2,7abeta-tetramethyleneoctahydro-1H-cyclopenta[c]pyridine-5beta-acetic acid 5,6-lactone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102103D          

 60 64  0  0  0  0            999 V2000
    3.3388    3.0400    0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2487    2.1794   -0.2497 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8433    0.9898    0.6497 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0295    1.4828    1.8863 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5108    0.8561    3.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5328    0.1517    3.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6903   -0.4410    4.7539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7423    0.1685    2.9048 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8828    0.7081    3.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4402    1.0692    1.7191 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4993    0.5120    0.2830 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7061    1.7166   -0.4786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -0.4461   -0.0883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4366   -1.0796   -1.4929 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1740   -0.2897   -2.6065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1773   -0.9628   -3.9666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4523    0.2070   -4.8910 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9173   -0.0110   -6.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7506    1.3255   -4.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4190    2.3984   -4.6389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5690    0.9851   -2.8516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0141   -1.2871   -1.8309 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4624   -2.6058   -2.2045 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8721   -3.3898   -0.9536 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8240   -2.6316   -0.0065 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1555   -1.4767    0.7800 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9053   -0.0914    0.0296 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0027   -0.4077   -1.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9905   -0.1970   -2.1412 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0015    3.5086    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2296    2.4428    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321    3.8397   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3965    2.8239   -0.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6490    1.8250   -1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7778    0.5130    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105    2.5640    2.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737   -0.8559    2.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069    0.7753    3.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0705    0.0510    4.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6518    1.7026    4.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0637    1.9730    1.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6713    1.5419   -1.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6978   -1.2677    0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6002    0.0662   -0.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9107   -2.0699   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2079   -0.1051   -2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9291   -1.7542   -4.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2012   -1.4000   -4.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5236    0.4370   -4.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1317    0.8564   -6.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3776   -0.8911   -6.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8306   -0.1512   -6.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3134   -3.1379   -2.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3331   -2.5009   -2.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0265   -3.6806   -0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3560   -4.3206   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153   -2.2808   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819   -3.3601    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -1.8787    1.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7947   -1.3055    1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  8  1  0  0  0  0
  4 36  1  1  0  0  0
  8  6  1  0  0  0  0
  6  7  2  0  0  0  0
 22 14  1  0  0  0  0
 14 13  1  0  0  0  0
 13 11  1  0  0  0  0
 27 11  1  0  0  0  0
  6  5  1  0  0  0  0
 27 26  1  1  0  0  0
 11 10  1  0  0  0  0
  4  3  1  0  0  0  0
  3 27  1  0  0  0  0
 15 21  1  0  0  0  0
  5  4  1  0  0  0  0
 26 25  1  0  0  0  0
  4 10  1  0  0  0  0
 25 24  1  0  0  0  0
  8  9  1  0  0  0  0
 21 19  1  0  0  0  0
 19 17  1  0  0  0  0
 17 16  1  0  0  0  0
 16 15  1  0  0  0  0
 14 15  1  0  0  0  0
 22 23  1  0  0  0  0
 15 46  1  1  0  0  0
 24 23  1  0  0  0  0
 11 12  1  6  0  0  0
 28 29  2  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
 27 28  1  0  0  0  0
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 10 41  1  6  0  0  0
 19 20  2  0  0  0  0
 28 22  1  0  0  0  0
 17 18  1  0  0  0  0
  8 37  1  6  0  0  0
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  3 35  1  1  0  0  0
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 12 42  1  0  0  0  0
  2 33  1  0  0  0  0
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  1 32  1  0  0  0  0
 18 50  1  0  0  0  0
 18 51  1  0  0  0  0
 18 52  1  0  0  0  0
M  END

     RDKit          3D

 60 64  0  0  0  0  0  0  0  0999 V2000
    3.3388    3.0400    0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2487    2.1794   -0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433    0.9898    0.6497 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0295    1.4828    1.8863 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5108    0.8561    3.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5328    0.1517    3.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6903   -0.4410    4.7539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7423    0.1685    2.9048 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8828    0.7081    3.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4402    1.0692    1.7191 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4993    0.5120    0.2830 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7061    1.7166   -0.4786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -0.4461   -0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4366   -1.0796   -1.4929 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1740   -0.2897   -2.6065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1773   -0.9628   -3.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7506    1.3255   -4.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8240   -2.6316   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1555   -1.4767    0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0027   -0.4077   -1.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9905   -0.1970   -2.1412 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2296    2.4428    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321    3.8397   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3965    2.8239   -0.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6490    1.8250   -1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7778    0.5130    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105    2.5640    2.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737   -0.8559    2.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2272   -1.8787    1.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7947   -1.3055    1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
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  4 36  1  1
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  6  7  2  0
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M  END


  Mrv1652306212102103D          

 60 64  0  0  0  0            999 V2000
    3.3388    3.0400    0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2487    2.1794   -0.2497 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8433    0.9898    0.6497 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0295    1.4828    1.8863 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5108    0.8561    3.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5328    0.1517    3.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6903   -0.4410    4.7539 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7423    0.1685    2.9048 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8828    0.7081    3.7596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4402    1.0692    1.7191 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4993    0.5120    0.2830 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7061    1.7166   -0.4786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -0.4461   -0.0883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4366   -1.0796   -1.4929 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1740   -0.2897   -2.6065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1773   -0.9628   -3.9666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4523    0.2070   -4.8910 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.7506    1.3255   -4.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4190    2.3984   -4.6389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5690    0.9851   -2.8516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0141   -1.2871   -1.8309 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4624   -2.6058   -2.2045 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8721   -3.3898   -0.9536 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.9053   -0.0914    0.0296 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0027   -0.4077   -1.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9905   -0.1970   -2.1412 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6490    1.8250   -1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7778    0.5130    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105    2.5640    2.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737   -0.8559    2.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7153   -2.2808   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819   -3.3601    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -1.8787    1.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7947   -1.3055    1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  8  1  0  0  0  0
  4 36  1  1  0  0  0
  8  6  1  0  0  0  0
  6  7  2  0  0  0  0
 22 14  1  0  0  0  0
 14 13  1  0  0  0  0
 13 11  1  0  0  0  0
 27 11  1  0  0  0  0
  6  5  1  0  0  0  0
 27 26  1  1  0  0  0
 11 10  1  0  0  0  0
  4  3  1  0  0  0  0
  3 27  1  0  0  0  0
 15 21  1  0  0  0  0
  5  4  1  0  0  0  0
 26 25  1  0  0  0  0
  4 10  1  0  0  0  0
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  8  9  1  0  0  0  0
 21 19  1  0  0  0  0
 19 17  1  0  0  0  0
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 14 15  1  0  0  0  0
 22 23  1  0  0  0  0
 15 46  1  1  0  0  0
 24 23  1  0  0  0  0
 11 12  1  6  0  0  0
 28 29  2  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
 27 28  1  0  0  0  0
 14 45  1  1  0  0  0
 10 41  1  6  0  0  0
 19 20  2  0  0  0  0
 28 22  1  0  0  0  0
 17 18  1  0  0  0  0
  8 37  1  6  0  0  0
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 13 43  1  0  0  0  0
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  3 35  1  1  0  0  0
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  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
 18 50  1  0  0  0  0
 18 51  1  0  0  0  0
 18 52  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042548

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12C([H])([H])[C@]([H])(N3C(=O)[C@@]1(C([H])([H])C([H])([H])C([H])([H])C3([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[H])[C@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])[C@]21[H])[C@@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H31NO6/c1-4-13-17-16(12(3)19(25)29-17)22(27)10-14(15-9-11(2)18(24)28-15)23-8-6-5-7-21(13,22)20(23)26/h11-17,27H,4-10H2,1-3H3/t11-,12-,13-,14-,15-,16-,17-,21+,22+/m0/s1

> <INCHI_KEY>
YOBIPOVYJKVGIS-IGYKYSAHSA-N

> <FORMULA>
C22H31NO6

> <MOLECULAR_WEIGHT>
405.491

> <EXACT_MASS>
405.215137722

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.53500965135051

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,3S,6S,7S,8R,10S)-2-ethyl-8-hydroxy-6-methyl-10-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatetracyclo[9.4.1.0^{1,8}.0^{3,7}]hexadecane-5,16-dione

> <ALOGPS_LOGP>
1.62

> <JCHEM_LOGP>
1.440692148666666

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.780548425102378

> <JCHEM_PKA_STRONGEST_BASIC>
0.3388002839792509

> <JCHEM_POLAR_SURFACE_AREA>
93.13999999999999

> <JCHEM_REFRACTIVITY>
101.85099999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3S,6S,7S,8R,10S)-2-ethyl-8-hydroxy-6-methyl-10-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatetracyclo[9.4.1.0^{1,8}.0^{3,7}]hexadecane-5,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 64  0  0  0  0  0  0  0  0999 V2000
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    1.8240   -2.6316   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0027   -0.4077   -1.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7153   -2.2808   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819   -3.3601    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -1.8787    1.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7947   -1.3055    1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  8  1  0
  4 36  1  1
  8  6  1  0
  6  7  2  0
 22 14  1  0
 14 13  1  0
 13 11  1  0
 27 11  1  0
  6  5  1  0
 27 26  1  1
 11 10  1  0
  4  3  1  0
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 26 25  1  0
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 25 24  1  0
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 19 17  1  0
 17 16  1  0
 16 15  1  0
 14 15  1  0
 22 23  1  0
 15 46  1  1
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 11 12  1  6
 28 29  2  0
  2  1  1  0
  3  2  1  0
 27 28  1  0
 14 45  1  1
 10 41  1  6
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 17 18  1  0
  8 37  1  6
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 26 59  1  0
 26 60  1  0
 25 57  1  0
 25 58  1  0
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  3 35  1  1
 17 49  1  6
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 18 50  1  0
 18 51  1  0
 18 52  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       3.339   3.040   0.386  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.249   2.179  -0.250  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.843   0.990   0.650  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.030   1.483   1.886  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.511   0.856   3.076  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.533   0.152   3.698  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.690  -0.441   4.754  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.742   0.169   2.905  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.883   0.708   3.760  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.440   1.069   1.719  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.499   0.512   0.283  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.706   1.717  -0.479  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.631  -0.446  -0.088  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.437  -1.080  -1.493  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.174  -0.290  -2.607  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.177  -0.963  -3.967  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.452   0.207  -4.891  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.917  -0.011  -6.293  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.751   1.325  -4.165  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.419   2.398  -4.639  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.569   0.985  -2.852  0.00  0.00           O+0
HETATM   22  N   UNK     0      -0.014  -1.287  -1.831  0.00  0.00           N+0
HETATM   23  C   UNK     0       0.462  -2.606  -2.204  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.872  -3.390  -0.954  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.824  -2.632  -0.007  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.155  -1.477   0.780  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.905  -0.091   0.030  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.003  -0.408  -1.449  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.990  -0.197  -2.141  0.00  0.00           O+0
HETATM   30  H   UNK     0       3.002   3.509   1.315  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.230   2.443   0.606  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.632   3.840  -0.302  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.397   2.824  -0.481  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.649   1.825  -1.202  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.778   0.513   0.974  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.111   2.564   2.035  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.974  -0.856   2.612  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.807   0.775   3.176  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.071   0.051   4.616  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.652   1.703   4.158  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.064   1.973   1.777  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.671   1.542  -1.441  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.698  -1.268   0.631  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.600   0.066  -0.040  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.911  -2.070  -1.454  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.208  -0.105  -2.285  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.929  -1.754  -4.042  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.201  -1.400  -4.203  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.524   0.437  -4.914  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.132   0.856  -6.927  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.378  -0.891  -6.753  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.831  -0.151  -6.292  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.313  -3.138  -2.764  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.333  -2.501  -2.862  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.027  -3.681  -0.395  0.00  0.00           H+0
HETATM   56  H   UNK     0       1.356  -4.321  -1.273  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.715  -2.281  -0.539  0.00  0.00           H+0
HETATM   58  H   UNK     0       2.182  -3.360   0.733  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.227  -1.879   1.190  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.795  -1.306   1.654  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3   33   34                                             
CONECT    3    4   27    2   35                                             
CONECT    4   36    3    5   10                                             
CONECT    5    6    4                                                       
CONECT    6    8    7    5                                                  
CONECT    7    6                                                            
CONECT    8   10    6    9   37                                             
CONECT    9    8   38   39   40                                             
CONECT   10    8   11    4   41                                             
CONECT   11   13   27   10   12                                             
CONECT   12   11   42                                                       
CONECT   13   14   11   43   44                                             
CONECT   14   22   13   15   45                                             
CONECT   15   21   16   14   46                                             
CONECT   16   17   15   47   48                                             
CONECT   17   19   16   18   49                                             
CONECT   18   17   50   51   52                                             
CONECT   19   21   17   20                                                  
CONECT   20   19                                                            
CONECT   21   15   19                                                       
CONECT   22   14   23   28                                                  
CONECT   23   22   24   53   54                                             
CONECT   24   25   23   55   56                                             
CONECT   25   26   24   57   58                                             
CONECT   26   27   25   59   60                                             
CONECT   27   11   26    3   28                                             
CONECT   28   29   27   22                                                  
CONECT   29   28                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    2                                                            
CONECT   34    2                                                            
CONECT   35    3                                                            
CONECT   36    4                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41   10                                                            
CONECT   42   12                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   16                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   18                                                            
CONECT   51   18                                                            
CONECT   52   18                                                            
CONECT   53   23                                                            
CONECT   54   23                                                            
CONECT   55   24                                                            
CONECT   56   24                                                            
CONECT   57   25                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  128    0
END

RDKit          3D

60 64  0  0  0  0  0  0  0  0999 V2000
    3.3388    3.0400    0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2487    2.1794   -0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8433    0.9898    0.6497 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0295    1.4828    1.8863 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5108    0.8561    3.0762 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5328    0.1517    3.6980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6903   -0.4410    4.7539 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4402    1.0692    1.7191 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4993    0.5120    0.2830 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7061    1.7166   -0.4786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313   -0.4461   -0.0883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4366   -1.0796   -1.4929 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1740   -0.2897   -2.6065 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1773   -0.9628   -3.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4523    0.2070   -4.8910 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.7506    1.3255   -4.1655 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0141   -1.2871   -1.8309 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4624   -2.6058   -2.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8721   -3.3898   -0.9536 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8240   -2.6316   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1555   -1.4767    0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9053   -0.0914    0.0296 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0027   -0.4077   -1.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9905   -0.1970   -2.1412 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0015    3.5086    1.3147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2296    2.4428    0.6060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321    3.8397   -0.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3965    2.8239   -0.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6490    1.8250   -1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7778    0.5130    0.9742 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1105    2.5640    2.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9737   -0.8559    2.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069    0.7753    3.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0705    0.0510    4.6158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6518    1.7026    4.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0637    1.9730    1.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6713    1.5419   -1.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6978   -1.2677    0.6306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6002    0.0662   -0.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9107   -2.0699   -1.4541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2079   -0.1051   -2.2854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9291   -1.7542   -4.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2012   -1.4000   -4.2031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5236    0.4370   -4.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1317    0.8564   -6.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3776   -0.8911   -6.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8306   -0.1512   -6.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3134   -3.1379   -2.7643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3331   -2.5009   -2.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0265   -3.6806   -0.3951 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3560   -4.3206   -1.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153   -2.2808   -0.5388 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1819   -3.3601    0.7331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2272   -1.8787    1.1896 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7947   -1.3055    1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  8  1  0
  4 36  1  1
  8  6  1  0
  6  7  2  0
 22 14  1  0
 14 13  1  0
 13 11  1  0
 27 11  1  0
  6  5  1  0
 27 26  1  1
 11 10  1  0
  4  3  1  0
  3 27  1  0
 15 21  1  0
  5  4  1  0
 26 25  1  0
  4 10  1  0
 25 24  1  0
  8  9  1  0
 21 19  1  0
 19 17  1  0
 17 16  1  0
 16 15  1  0
 14 15  1  0
 22 23  1  0
 15 46  1  1
 24 23  1  0
 11 12  1  6
 28 29  2  0
  2  1  1  0
  3  2  1  0
 27 28  1  0
 14 45  1  1
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 19 20  2  0
 28 22  1  0
 17 18  1  0
  8 37  1  6
  9 38  1  0
  9 39  1  0
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 13 43  1  0
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  3 35  1  1
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 16 48  1  0
 12 42  1  0
  2 33  1  0
  2 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
 18 50  1  0
 18 51  1  0
 18 52  1  0
M  END

View in JSmol

Synonyms

Value	Source
(AlphaS)-a-methyl-1-oxo-3a-(4a-methyl-5-oxotetrahydrofuran-2a-yl)-4aalpha,6b-dihydroxy-7a-ethyl-2,7abeta-tetramethyleneoctahydro-1H-cyclopenta[c]pyridine-5b-acetate 5,6-lactone	Generator
(AlphaS)-a-methyl-1-oxo-3a-(4a-methyl-5-oxotetrahydrofuran-2a-yl)-4aalpha,6b-dihydroxy-7a-ethyl-2,7abeta-tetramethyleneoctahydro-1H-cyclopenta[c]pyridine-5b-acetic acid 5,6-lactone	Generator
(AlphaS)-alpha-methyl-1-oxo-3alpha-(4alpha-methyl-5-oxotetrahydrofuran-2alpha-yl)-4aalpha,6beta-dihydroxy-7alpha-ethyl-2,7abeta-tetramethyleneoctahydro-1H-cyclopenta[c]pyridine-5beta-acetate 5,6-lactone	Generator
(AlphaS)-α-methyl-1-oxo-3α-(4α-methyl-5-oxotetrahydrofuran-2α-yl)-4aalpha,6β-dihydroxy-7α-ethyl-2,7abeta-tetramethyleneoctahydro-1H-cyclopenta[c]pyridine-5β-acetate 5,6-lactone	Generator
(AlphaS)-α-methyl-1-oxo-3α-(4α-methyl-5-oxotetrahydrofuran-2α-yl)-4aalpha,6β-dihydroxy-7α-ethyl-2,7abeta-tetramethyleneoctahydro-1H-cyclopenta[c]pyridine-5β-acetic acid 5,6-lactone	Generator

Chemical Formula

C₂₂H₃₁NO₆

Average Mass

405.4910 Da

Monoisotopic Mass

405.21514 Da

IUPAC Name

(1S,2R,3S,6S,7S,8R,10S)-2-ethyl-8-hydroxy-6-methyl-10-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatetracyclo[9.4.1.0^{1,8}.0^{3,7}]hexadecane-5,16-dione

Traditional Name

(1S,2R,3S,6S,7S,8R,10S)-2-ethyl-8-hydroxy-6-methyl-10-[(2S,4S)-4-methyl-5-oxooxolan-2-yl]-4-oxa-11-azatetracyclo[9.4.1.0^{1,8}.0^{3,7}]hexadecane-5,16-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@@]12C([H])([H])[C@]([H])(N3C(=O)[C@@]1(C([H])([H])C([H])([H])C([H])([H])C3([H])[H])[C@@]([H])(C([H])([H])C([H])([H])[H])[C@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])[C@]21[H])[C@@]1([H])OC(=O)[C@@]([H])(C([H])([H])[H])C1([H])[H]

InChI Identifier

InChI=1S/C22H31NO6/c1-4-13-17-16(12(3)19(25)29-17)22(27)10-14(15-9-11(2)18(24)28-15)23-8-6-5-7-21(13,22)20(23)26/h11-17,27H,4-10H2,1-3H3/t11-,12-,13-,14-,15-,16-,17-,21+,22+/m0/s1

InChI Key

YOBIPOVYJKVGIS-IGYKYSAHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Stemona tuberosa	JEOL database	Hitotsuyanagi, Y., et al, Tetrahedron 69, 6297 (2013)

Chemical Taxonomy

Classification

Not classified

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	1.62	ALOGPS
logP	1.44	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	13.78	ChemAxon
pKa (Strongest Basic)	0.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	93.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	101.85 m³·mol⁻¹	ChemAxon
Polarizability	42.54 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

102099769

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hitotsuyanagi, Y., et al. (2013). Hitotsuyanagi, Y., et al, Tetrahedron 69, 6297 (2013). Tetrahedron.

Showing NP-Card for stemona-lactam Q (NP0042548)

MOL for NP0042548 (stemona-lactam Q)

3D MOL for NP0042548 (stemona-lactam Q)

3D SDF for NP0042548 (stemona-lactam Q)

3D-SDF for NP0042548 (stemona-lactam Q)

PDB for NP0042548 (stemona-lactam Q)

3D PDB for NP0042548 (stemona-lactam Q)

SMILES for NP0042548 (stemona-lactam Q)

INCHI for NP0042548 (stemona-lactam Q)

Structure for NP0042548 (stemona-lactam Q)

3D Structure for NP0042548 (stemona-lactam Q)