NP-MRD: Showing NP-Card for (1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate (NP0141856)

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Record Information

Version

2.0

Created at

2022-09-01 20:15:48 UTC

Updated at

2022-09-01 20:15:48 UTC

NP-MRD ID

NP0141856

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

Description

Florosenine, also known as acetylotosenine or acetylfukinotoxin, belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. Florosenine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate is found in Jacobaea adonidifolia, Packera glabella, Packera aurea, Senecio flaccidus, Senecio inaequidens, Senecio leptolobus and Senecio sarracenicus. (1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate was first documented in 1985 (PMID: 4005849). Based on a literature review a small amount of articles have been published on florosenine (PMID: 17913058) (PMID: 3394160) (PMID: 8646334).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309012222152D          

 30 32  0  0  1  0            999 V2000
    5.1491   -1.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311   -0.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4520   -0.5935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2766    0.2763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5657    0.8463    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6345   -0.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7471    0.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6085    1.9193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486    0.2920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4301    0.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1100    1.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3144    0.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5976    1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3795    2.1415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4465    2.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7880    2.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5836    3.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885    2.5732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7870    3.2306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6056    3.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1320    3.8091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9256    2.3671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7441    2.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0642    1.5037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9057    1.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226    1.5486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1652    2.0471    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2951    1.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6085    1.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2353    1.2327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
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 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
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  5 24  1  0  0  0  0
 24 25  1  1  0  0  0
 22 26  1  1  0  0  0
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 27 28  1  1  0  0  0
 18 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END

     RDKit          3D

 59 61  0  0  0  0  0  0  0  0999 V2000
   -6.0027   -2.6179    0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5019   -2.4713    0.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7589   -3.4852    0.0516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9295   -1.2344    0.1540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5094   -0.9915    0.1607 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0072   -1.6090    1.4690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8635   -1.6525   -1.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5814   -2.0240   -0.9553 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6597   -1.5364   -1.2185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5605   -1.1817   -0.0968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002   -2.1464   -0.1531 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9570   -2.3088    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5447   -1.0552    0.5590 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9763   -1.1819    0.6723 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1258    0.0916   -0.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600    1.1306    0.7335 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0821    1.3496    0.5343 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8434    1.7946   -0.7651 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5665    2.1199   -1.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5174    2.4606   -2.4691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650    2.0943   -0.4786 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7260    1.1415   -0.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3679    0.4914    0.2108 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7161    1.2054    0.4208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7292    2.5758    0.8202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2092    3.4691   -0.1035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3370    4.6566   -0.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4260   -0.0202    0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7435    0.0438    1.8031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2388   -3.6168    0.5010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4273   -1.8811    0.8330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4377   -2.3945   -0.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8788   -0.7774    2.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7427   -2.3476    1.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7200   -0.6617   -1.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1384   -2.3484   -1.8759 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4881   -2.6566   -0.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4055   -0.1386    0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4393   -1.7498   -0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2179   -1.6494    1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5023   -0.1257   -1.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0904    0.4955   -0.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0662    2.1183    0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8104    0.9120    1.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7214    2.0521    1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4646    1.7863   -1.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819    0.4243   -1.7286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8103    0.7598    1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0926    1.5835   -0.5696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4623    0.5142    0.8475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6317    2.0726    1.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2861    3.6573   -0.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5186    5.4087    0.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273    5.1002   -1.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7079    4.3016   -0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
 28 27  1  0
 27 26  1  0
 22 26  1  1
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 24  5  1  0
  5  6  1  0
  5  4  1  6
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  7  9  1  0
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 13 14  1  0
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 12 39  1  0
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 15 43  1  0
 15 44  1  0
 16 45  1  0
 16 46  1  0
 17 47  1  0
 17 48  1  0
 18 49  1  1
M  END


  Mrv1652309012222152D          

 30 32  0  0  1  0            999 V2000
    5.1491   -1.1804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6311   -0.5109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4520   -0.5935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2766    0.2763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5657    0.8463    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6345   -0.0639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7471    0.9494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6085    1.9193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2486    0.2920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4301    0.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1100    1.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3144    0.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5976    1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3795    2.1415    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4465    2.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7880    2.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5836    3.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2885    2.5732    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7870    3.2306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6056    3.1275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1320    3.8091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9256    2.3671    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7441    2.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0642    1.5037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9057    1.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226    1.5486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1652    2.0471    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2951    1.8678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6085    1.8128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2353    1.2327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  5 24  1  0  0  0  0
 24 25  1  1  0  0  0
 22 26  1  1  0  0  0
 26 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  1  0  0  0
 18 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0141856

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@]11C[C@@H](C)[C@@](C)(OC(C)=O)C(=O)OC\C2=C\CN(C)CC[C@@H](OC1=O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H29NO8/c1-12-10-21(13(2)29-21)19(26)28-16-7-9-22(5)8-6-15(17(16)24)11-27-18(25)20(12,4)30-14(3)23/h6,12-13,16H,7-11H2,1-5H3/b15-6-/t12-,13+,16-,20-,21+/m1/s1

> <INCHI_KEY>
RNNVXCSFOWGBQP-DIOQTCHZSA-N

> <FORMULA>
C21H29NO8

> <MOLECULAR_WEIGHT>
423.462

> <EXACT_MASS>
423.189316898

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
42.689684318823126

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3'S,4S,6R,7R,11Z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

> <ALOGPS_LOGP>
1.23

> <JCHEM_LOGP>
1.3555689673333327

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.594389675725534

> <JCHEM_PKA_STRONGEST_BASIC>
6.930394422805697

> <JCHEM_POLAR_SURFACE_AREA>
111.74000000000001

> <JCHEM_REFRACTIVITY>
104.7343

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3'S,4S,6R,7R,11Z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-SEP-22         0                                  
HETATM    1  C   UNK     0       9.612  -2.203   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.511  -0.954   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.044  -1.108   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.850   0.516   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.523   1.580   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.651  -0.119   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.995   1.772   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.736   3.583   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       6.064   0.545   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.536   0.737   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.939   2.157   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.454   1.750   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.115   2.512   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.708   3.997   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -0.833   4.366   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.471   5.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.956   5.743   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.272   4.803   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.202   6.030   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.730   5.838   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.713   7.110   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.328   4.419   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.856   4.226   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.453   2.807   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.024   3.122   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.135   2.891   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.908   3.821   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.284   3.487   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.869   3.384   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.039   2.301   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   24                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   26   27                                             
CONECT   23   22   24                                                       
CONECT   24   23    5   25                                                  
CONECT   25   24                                                            
CONECT   26   22   27                                                       
CONECT   27   26   22   28                                                  
CONECT   28   27                                                            
CONECT   29   18   11   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
Acetylfukinotoxin	ChEBI
Acetylotosenine	ChEBI
O-Acetylotosenine	ChEBI
Otosenine 12-acetate	ChEBI
Otosenine 12-acetic acid	Generator

Chemical Formula

C₂₁H₂₉NO₈

Average Mass

423.4620 Da

Monoisotopic Mass

423.18932 Da

IUPAC Name

(1R,3'S,4S,6R,7R,11Z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

Traditional Name

(1R,3'S,4S,6R,7R,11Z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@]11C[C@@H](C)[C@@](C)(OC(C)=O)C(=O)OC\C2=C\CN(C)CC[C@@H](OC1=O)C2=O

InChI Identifier

InChI=1S/C21H29NO8/c1-12-10-21(13(2)29-21)19(26)28-16-7-9-22(5)8-6-15(17(16)24)11-27-18(25)20(12,4)30-14(3)23/h6,12-13,16H,7-11H2,1-5H3/b15-6-/t12-,13+,16-,20-,21+/m1/s1

InChI Key

RNNVXCSFOWGBQP-DIOQTCHZSA-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
Jacobaea adonidifolia	LOTUS Database	35616633
Packera glabella	LOTUS Database	35616633
Senecio aureus	LOTUS Database	35616633
Senecio flaccidus	LOTUS Database	35616633
Senecio inaequidens	LOTUS Database	35616633
Senecio leptolobus	LOTUS Database	35616633
Senecio sarracenicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Azaspirodecane
Tricarboxylic acid or derivatives
Alpha-acyloxy ketone
Tertiary aliphatic amine
Tertiary amine
Lactone
Ketone
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Azacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.23	ALOGPS
logP	1.36	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	16.59	ChemAxon
pKa (Strongest Basic)	6.93	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	111.74 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.73 m³·mol⁻¹	ChemAxon
Polarizability	42.69 Å³	ChemAxon
Number of Rings	3	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

C00026194

Chemspider ID

76962859

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122362136

PDB ID

Not Available

ChEBI ID

136490

Good Scents ID

Not Available

References

General References

Mori H, Sugie S, Yoshimi N, Asada Y, Furuya T, Williams GM: Genotoxicity of a variety of pyrrolizidine alkaloids in the hepatocyte primary culture-DNA repair test using rat, mouse, and hamster hepatocytes. Cancer Res. 1985 Jul;45(7):3125-9. [PubMed:4005849 ]
Tundis R, Loizzo MR, Statti GA, Passalacqua NG, Peruzzi L, Menichini F: Pyrrolizidine alkaloid profiles of the Senecio cineraria group (Asteraceae). Z Naturforsch C J Biosci. 2007 Jul-Aug;62(7-8):467-72. doi: 10.1515/znc-2007-7-802. [PubMed:17913058 ]
Habermehl GG, Martz W, Tokarnia CH, Dobereiner J, Mendez MC: Livestock poisoning in South America by species of the Senecio plant. Toxicon. 1988;26(3):275-86. doi: 10.1016/0041-0101(88)90218-8. [PubMed:3394160 ]
Copper RA, Bowers RJ, Beckham CJ, uxtable RJ: Preparative separation of pyrrolizidine alkaloids by high-speed counter-current chromatography. J Chromatogr A. 1996 Apr 26;732(1):43-50. doi: 10.1016/0021-9673(95)01241-9. [PubMed:8646334 ]
LOTUS database [Link]

Showing NP-Card for (1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate (NP0141856)

MOL for NP0141856 ((1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate)

3D MOL for NP0141856 ((1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate)

3D SDF for NP0141856 ((1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate)

3D-SDF for NP0141856 ((1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate)

PDB for NP0141856 ((1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate)

3D PDB for NP0141856 ((1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate)

SMILES for NP0141856 ((1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate)

INCHI for NP0141856 ((1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate)

Structure for NP0141856 ((1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate)

3D Structure for NP0141856 ((1r,3's,4s,6r,7r,11z)-3',6,7,14-tetramethyl-3,8,17-trioxo-2,9-dioxa-14-azaspiro[bicyclo[9.5.1]heptadecane-4,2'-oxiran]-11-en-7-yl acetate)