NP-MRD: Showing NP-Card for secuamamine F (NP0038634)

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Record Information

Version

2.0

Created at

2021-06-20 21:16:19 UTC

Updated at

2021-06-30 00:11:31 UTC

NP-MRD ID

NP0038634

Secondary Accession Numbers

None

Natural Product Identification

Common Name

secuamamine F

Provided By

JEOL Database JEOL Logo

Description

(1S,9aalpha)-1alpha,1,4beta-[2-Oxo-1-oxa-3-[(S)-2alpha-piperidinyl]-3-pentene-1,4,5-triyl]octahydro-2H-quinolizine-3beta-ol belongs to the class of organic compounds known as quinolizidines. Quinolizidines are compounds containing a quinolizidine moiety, which is a octahydro-2H-quinolizine derivative. secuamamine F is found in Flueggea suffruticosa and Securinega suffruticosa var. amamiensis. secuamamine F was first documented in 2009 (Ohsaki, A., et al.). Based on a literature review very few articles have been published on (1S,9aalpha)-1alpha,1,4beta-[2-Oxo-1-oxa-3-[(S)-2alpha-piperidinyl]-3-pentene-1,4,5-triyl]octahydro-2H-quinolizine-3beta-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123163D          

 49 53  0  0  0  0            999 V2000
    1.0519    4.3778    0.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471    3.4064    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1834    3.4672   -1.0706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0577    2.1492   -1.5279 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7755    1.8038   -2.7739 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5168    0.3289   -3.1432 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7626   -0.3621   -3.2278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4220   -0.3298   -2.0809 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2357   -0.1816   -0.6695 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4245    1.2810   -0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228    1.9990    0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4975    1.6672    1.9268 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0042    1.9881    1.9786 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5906    1.6801    3.3557 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2486    0.2591    3.7890 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7524   -0.0126    3.6556 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2780    0.2528    2.2944 N   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7236    0.3873   -2.1779 N   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8131   -0.2941   -1.4786 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1028    0.5174   -1.5811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9594    1.9225   -0.9967 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5091    2.2855   -0.6864 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5629    1.8316   -1.8143 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8425    2.0031   -2.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5853   -1.2239   -3.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5409   -1.3938   -2.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4018   -0.6284    0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1868    3.0445    1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5413    1.4049    1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8089   -0.4546    3.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.9166   -0.0121   -1.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.4360    3.3693   -0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2253    1.8219    0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8533    2.4101   -2.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0  0  0  0
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 23 49  1  6  0  0  0
  8 28  1  6  0  0  0
  6 26  1  6  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  7 27  1  0  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
    1.0519    4.3778    0.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471    3.4064    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1834    3.4672   -1.0706 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5168    0.3289   -3.1432 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.5906    1.6801    3.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486    0.2591    3.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7524   -0.0126    3.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7236    0.3873   -2.1779 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8131   -0.2941   -1.4786 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5629    1.8316   -1.8143 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.5853   -1.2239   -3.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306202123163D          

 49 53  0  0  0  0            999 V2000
    1.0519    4.3778    0.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471    3.4064    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7626   -0.3621   -3.2278 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4975    1.6672    1.9268 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0042    1.9881    1.9786 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5906    1.6801    3.3557 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2486    0.2591    3.7890 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7524   -0.0126    3.6556 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2780    0.2528    2.2944 N   0  0  2  0  0  0  0  0  0  0  0  0
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 21 20  1  0  0  0  0
 12 17  1  0  0  0  0
 23  4  1  0  0  0  0
 18  8  1  0  0  0  0
  8  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  4  1  0  0  0  0
 12 13  1  0  0  0  0
  6  7  1  0  0  0  0
 17 16  1  0  0  0  0
  8  9  1  0  0  0  0
 21 22  1  0  0  0  0
  4 10  1  0  0  0  0
 10  9  1  0  0  0  0
 20 19  1  0  0  0  0
  4  3  1  1  0  0  0
 19 18  1  0  0  0  0
  3  2  1  0  0  0  0
 23 22  1  0  0  0  0
 10 11  2  0  0  0  0
 11  2  1  0  0  0  0
 23 18  1  0  0  0  0
  2  1  2  0  0  0  0
 12 11  1  0  0  0  0
 12 31  1  1  0  0  0
 17 40  1  0  0  0  0
 16 38  1  0  0  0  0
 16 39  1  0  0  0  0
 15 36  1  0  0  0  0
 15 37  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 22 47  1  0  0  0  0
 22 48  1  0  0  0  0
 23 49  1  6  0  0  0
  8 28  1  6  0  0  0
  6 26  1  6  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  7 27  1  0  0  0  0
  9 29  1  0  0  0  0
  9 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038634

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])[C@]23OC(=O)C(=C2C([H])([H])[C@@]1([H])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@]31[H])[C@@]1([H])N([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H26N2O3/c21-14-10-18-11(9-13(14)20-8-4-2-6-15(18)20)16(17(22)23-18)12-5-1-3-7-19-12/h12-15,19,21H,1-10H2/t12-,13+,14+,15-,18-/m0/s1

> <INCHI_KEY>
OXYAQOXZSUFYEP-KIBLCYBISA-N

> <FORMULA>
C18H26N2O3

> <MOLECULAR_WEIGHT>
318.417

> <EXACT_MASS>
318.194342705

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
34.76164766087311

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,8R,15R)-15-hydroxy-11-[(2S)-piperidin-2-yl]-13-oxa-7-azatetracyclo[6.5.2.0^{1,10}.0^{2,7}]pentadec-10-en-12-one

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
0.8872355399999999

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.47548411992896

> <JCHEM_PKA_STRONGEST_BASIC>
8.702007003022706

> <JCHEM_POLAR_SURFACE_AREA>
61.800000000000004

> <JCHEM_REFRACTIVITY>
86.0941

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,8R,15R)-15-hydroxy-11-[(2S)-piperidin-2-yl]-13-oxa-7-azatetracyclo[6.5.2.0^{1,10}.0^{2,7}]pentadec-10-en-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
    1.0519    4.3778    0.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471    3.4064    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1834    3.4672   -1.0706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0577    2.1492   -1.5279 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7755    1.8038   -2.7739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5168    0.3289   -3.1432 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7626   -0.3621   -3.2278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4220   -0.3298   -2.0809 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2357   -0.1816   -0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4245    1.2810   -0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228    1.9990    0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4975    1.6672    1.9268 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0042    1.9881    1.9786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5906    1.6801    3.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486    0.2591    3.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7524   -0.0126    3.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2780    0.2528    2.2944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236    0.3873   -2.1779 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8131   -0.2941   -1.4786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1028    0.5174   -1.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9594    1.9225   -0.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091    2.2855   -0.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629    1.8316   -1.8143 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8425    2.0031   -2.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798    2.4570   -3.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565    0.2808   -4.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5853   -1.2239   -3.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5409   -1.3938   -2.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2023   -0.6969   -0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018   -0.6284    0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722    2.2878    2.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1868    3.0445    1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5413    1.4049    1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6775    1.8165    3.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1882    2.3908    4.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8089   -0.4546    3.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5646    0.1012    4.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1856    0.5901    4.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5514   -1.0616    3.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8184   -0.3284    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5791   -0.4703   -0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814   -1.2754   -1.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4018    0.5949   -2.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9166   -0.0121   -1.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5553    2.0093   -0.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3795    2.6479   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4360    3.3693   -0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2253    1.8219    0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8533    2.4101   -2.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 21 20  1  0
 12 17  1  0
 23  4  1  0
 18  8  1  0
  8  6  1  0
  6  5  1  0
  5  4  1  0
 12 13  1  0
  6  7  1  0
 17 16  1  0
  8  9  1  0
 21 22  1  0
  4 10  1  0
 10  9  1  0
 20 19  1  0
  4  3  1  1
 19 18  1  0
  3  2  1  0
 23 22  1  0
 10 11  2  0
 11  2  1  0
 23 18  1  0
  2  1  2  0
 12 11  1  0
 12 31  1  1
 17 40  1  0
 16 38  1  0
 16 39  1  0
 15 36  1  0
 15 37  1  0
 14 34  1  0
 14 35  1  0
 13 32  1  0
 13 33  1  0
 21 45  1  0
 21 46  1  0
 20 43  1  0
 20 44  1  0
 19 41  1  0
 19 42  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  6
  8 28  1  6
  6 26  1  6
  5 24  1  0
  5 25  1  0
  7 27  1  0
  9 29  1  0
  9 30  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  O   UNK     0       1.052   4.378   0.843  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.747   3.406   0.173  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.183   3.467  -1.071  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.058   2.149  -1.528  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.776   1.804  -2.774  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.517   0.329  -3.143  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.763  -0.362  -3.228  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.422  -0.330  -2.081  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.236  -0.182  -0.670  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.425   1.281  -0.419  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.923   1.999   0.587  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.498   1.667   1.927  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.004   1.988   1.979  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.591   1.680   3.356  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.249   0.259   3.789  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.752  -0.013   3.656  0.00  0.00           C+0
HETATM   17  N   UNK     0       1.278   0.253   2.294  0.00  0.00           N+0
HETATM   18  N   UNK     0      -1.724   0.387  -2.178  0.00  0.00           N+0
HETATM   19  C   UNK     0      -2.813  -0.294  -1.479  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.103   0.517  -1.581  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.959   1.923  -0.997  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.509   2.285  -0.686  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.563   1.832  -1.814  0.00  0.00           C+0
HETATM   24  H   UNK     0       1.843   2.003  -2.609  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.480   2.457  -3.605  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.057   0.281  -4.138  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.585  -1.224  -3.644  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.541  -1.394  -2.318  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.202  -0.697  -0.654  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.402  -0.628   0.099  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.972   2.288   2.666  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.187   3.045   1.749  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.541   1.405   1.218  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.678   1.817   3.340  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.188   2.391   4.088  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.809  -0.455   3.172  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.565   0.101   4.826  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.186   0.590   4.375  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.551  -1.062   3.899  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.818  -0.328   1.653  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.579  -0.470  -0.422  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.981  -1.275  -1.938  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.402   0.595  -2.635  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.917  -0.012  -1.072  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.555   2.009  -0.080  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.380   2.648  -1.704  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.436   3.369  -0.538  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.225   1.822   0.267  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.853   2.410  -2.703  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3   11    1                                                  
CONECT    3    4    2                                                       
CONECT    4   23    5   10    3                                             
CONECT    5    6    4   24   25                                             
CONECT    6    8    5    7   26                                             
CONECT    7    6   27                                                       
CONECT    8   18    6    9   28                                             
CONECT    9    8   10   29   30                                             
CONECT   10    4    9   11                                                  
CONECT   11   10    2   12                                                  
CONECT   12   17   13   11   31                                             
CONECT   13   14   12   32   33                                             
CONECT   14   15   13   34   35                                             
CONECT   15   16   14   36   37                                             
CONECT   16   15   17   38   39                                             
CONECT   17   12   16   40                                                  
CONECT   18    8   19   23                                                  
CONECT   19   20   18   41   42                                             
CONECT   20   21   19   43   44                                             
CONECT   21   20   22   45   46                                             
CONECT   22   21   23   47   48                                             
CONECT   23    4   22   18   49                                             
CONECT   24    5                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    7                                                            
CONECT   28    8                                                            
CONECT   29    9                                                            
CONECT   30    9                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   13                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   15                                                            
CONECT   37   15                                                            
CONECT   38   16                                                            
CONECT   39   16                                                            
CONECT   40   17                                                            
CONECT   41   19                                                            
CONECT   42   19                                                            
CONECT   43   20                                                            
CONECT   44   20                                                            
CONECT   45   21                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   22                                                            
CONECT   49   23                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  106    0
END

RDKit          3D

49 53  0  0  0  0  0  0  0  0999 V2000
    1.0519    4.3778    0.8426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7471    3.4064    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1834    3.4672   -1.0706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0577    2.1492   -1.5279 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7755    1.8038   -2.7739 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5168    0.3289   -3.1432 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7626   -0.3621   -3.2278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4220   -0.3298   -2.0809 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2357   -0.1816   -0.6695 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4245    1.2810   -0.4186 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228    1.9990    0.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4975    1.6672    1.9268 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0042    1.9881    1.9786 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5906    1.6801    3.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486    0.2591    3.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7524   -0.0126    3.6556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2780    0.2528    2.2944 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236    0.3873   -2.1779 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8131   -0.2941   -1.4786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1028    0.5174   -1.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9594    1.9225   -0.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5091    2.2855   -0.6864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5629    1.8316   -1.8143 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8425    2.0031   -2.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798    2.4570   -3.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565    0.2808   -4.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5853   -1.2239   -3.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5409   -1.3938   -2.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2023   -0.6969   -0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4018   -0.6284    0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722    2.2878    2.6660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1868    3.0445    1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5413    1.4049    1.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6775    1.8165    3.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1882    2.3908    4.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8089   -0.4546    3.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5646    0.1012    4.8262 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1856    0.5901    4.3754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5514   -1.0616    3.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8184   -0.3284    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5791   -0.4703   -0.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814   -1.2754   -1.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4018    0.5949   -2.6347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9166   -0.0121   -1.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5553    2.0093   -0.0804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3795    2.6479   -1.7043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4360    3.3693   -0.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2253    1.8219    0.2665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8533    2.4101   -2.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 21 20  1  0
 12 17  1  0
 23  4  1  0
 18  8  1  0
  8  6  1  0
  6  5  1  0
  5  4  1  0
 12 13  1  0
  6  7  1  0
 17 16  1  0
  8  9  1  0
 21 22  1  0
  4 10  1  0
 10  9  1  0
 20 19  1  0
  4  3  1  1
 19 18  1  0
  3  2  1  0
 23 22  1  0
 10 11  2  0
 11  2  1  0
 23 18  1  0
  2  1  2  0
 12 11  1  0
 12 31  1  1
 17 40  1  0
 16 38  1  0
 16 39  1  0
 15 36  1  0
 15 37  1  0
 14 34  1  0
 14 35  1  0
 13 32  1  0
 13 33  1  0
 21 45  1  0
 21 46  1  0
 20 43  1  0
 20 44  1  0
 19 41  1  0
 19 42  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  6
  8 28  1  6
  6 26  1  6
  5 24  1  0
  5 25  1  0
  7 27  1  0
  9 29  1  0
  9 30  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1S,9Aalpha)-1a,1,4b-[2-oxo-1-oxa-3-[(S)-2a-piperidinyl]-3-pentene-1,4,5-triyl]octahydro-2H-quinolizine-3b-ol	Generator
(1S,9Aalpha)-1α,1,4β-[2-oxo-1-oxa-3-[(S)-2α-piperidinyl]-3-pentene-1,4,5-triyl]octahydro-2H-quinolizine-3β-ol	Generator

Chemical Formula

C₁₈H₂₆N₂O₃

Average Mass

318.4170 Da

Monoisotopic Mass

318.19434 Da

IUPAC Name

(1S,2S,8R,15R)-15-hydroxy-11-[(2S)-piperidin-2-yl]-13-oxa-7-azatetracyclo[6.5.2.0^{1,10}.0^{2,7}]pentadec-10-en-12-one

Traditional Name

(1S,2S,8R,15R)-15-hydroxy-11-[(2S)-piperidin-2-yl]-13-oxa-7-azatetracyclo[6.5.2.0^{1,10}.0^{2,7}]pentadec-10-en-12-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C([H])([H])[C@]23OC(=O)C(=C2C([H])([H])[C@@]1([H])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@]31[H])[C@@]1([H])N([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H]

InChI Identifier

InChI=1S/C18H26N2O3/c21-14-10-18-11(9-13(14)20-8-4-2-6-15(18)20)16(17(22)23-18)12-5-1-3-7-19-12/h12-15,19,21H,1-10H2/t12-,13+,14+,15-,18-/m0/s1

InChI Key

OXYAQOXZSUFYEP-KIBLCYBISA-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
Flueggea suffruticosa	LOTUS Database	35616633
Securinega suffruticosa var. amamiensis	JEOL database	Ohsaki, A., et al, Tetrahedron Lett. 50, 6965 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinolizidines. Quinolizidines are compounds containing a quinolizidine moiety, which is a octahydro-2H-quinolizine derivative.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolizidines

Sub Class

Not Available

Direct Parent

Quinolizidines

Alternative Parents

Substituents

Azaspirodecane
Quinolizidine
2-furanone
Piperidine
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Tertiary aliphatic amine
Tertiary amine
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Secondary aliphatic amine
Azacycle
Secondary amine
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Organic oxide
Amine
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.21	ALOGPS
logP	0.89	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	14.48	ChemAxon
pKa (Strongest Basic)	8.7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.8 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	86.09 m³·mol⁻¹	ChemAxon
Polarizability	34.76 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

44552366

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ohsaki, A., et al. (2009). Ohsaki, A., et al, Tetrahedron Lett. 50, 6965 (2009). Tetrahedron Lett.

Showing NP-Card for secuamamine F (NP0038634)

MOL for NP0038634 (secuamamine F)

3D MOL for NP0038634 (secuamamine F)

3D SDF for NP0038634 (secuamamine F)

3D-SDF for NP0038634 (secuamamine F)

PDB for NP0038634 (secuamamine F)

3D PDB for NP0038634 (secuamamine F)

SMILES for NP0038634 (secuamamine F)

INCHI for NP0038634 (secuamamine F)

Structure for NP0038634 (secuamamine F)

3D Structure for NP0038634 (secuamamine F)