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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:34:17 UTC

Update Date

2022-03-07 02:53:52 UTC

HMDB ID

HMDB0033805

Secondary Accession Numbers

HMDB33805

Metabolite Identification

Common Name

Azaspiracid

Description

Azaspiracid 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. Azaspiracid is a very strong basic compound (based on its pKa). Outside of the human body, azaspiracid has been detected, but not quantified in, mollusks. This could make azaspiracid a potential biomarker for the consumption of these foods. Digestive glands were shown to contain ~1 μg/g AZAtotal with three AZA analogues present (in μg/g digestive gland): AZA1 (0.5), AZA2 (0.06), and AZA3 (0.44). Similar to DSP toxins, human consumption of AZA-contaminated shellfish can result in severe acute symptoms that include nausea, vomiting, diarrhea, and stomach cramps. Azaspiracid was first identified in the 1990s following an outbreak of human illness in the Netherlands that was associated with ingestion of contaminated shellfish originating from Killary Harbour, Ireland.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241217562D          

 60 68  0  0  0  0            999 V2000
    0.4708    2.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4708    1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845    1.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8967    1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8967    2.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845    2.9787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3870    3.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4199    3.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8352    2.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2853    2.2308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3150    3.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1372    3.4365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4782    2.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9984    2.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1789    2.0933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    1.4884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1630    2.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6804    2.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3393    1.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1643    1.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5767    0.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4017    0.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8142   -0.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6392   -0.1671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4017   -0.8820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879    2.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4017    1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4017    2.8714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879    0.7280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4017    0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2267    0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6392    0.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2267    1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6392    2.1552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6392   -0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879   -0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4017   -1.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1630   -0.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7518   -1.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9269   -1.4168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5144   -2.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9269   -2.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7518   -2.8467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1630   -2.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1689   -0.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9314   -1.5489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3439   -0.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7899   -0.2206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0337   -0.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1202   -1.3838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0337    0.2660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811    0.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3962    0.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3962   -0.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811   -0.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1630   -3.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811   -1.7963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1111    0.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6043    1.2298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2440    1.3302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1 10  1  0  0  0  0
  2  3  1  0  0  0  0
  2 60  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 16  1  0  0  0  0
  5  6  1  0  0  0  0
  5 18  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 26  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 33  1  0  0  0  0
 27 59  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 36  1  0  0  0  0
 31 32  1  0  0  0  0
 31 35  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 44  1  0  0  0  0
 39 45  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 46  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 56  1  0  0  0  0
 45 47  1  0  0  0  0
 46 47  1  0  0  0  0
 46 50  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 49 55  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 58  1  0  0  0  0
 54 55  1  0  0  0  0
 55 57  1  0  0  0  0
M  END

HMDB0033805
     RDKit          3D
Azaspiracid
131139  0  0  0  0  0  0  0  0999 V2000
   -2.2022   -2.2519   -0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8722   -1.4399    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2146   -1.8505    0.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3884   -0.9888    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4123   -0.8348   -1.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0797    0.3704   -1.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3229    0.9789   -2.8329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3773    1.4441   -0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3855    0.9839    0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3313    0.1491    1.0908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6762    0.2999    1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6791    0.8087    0.3235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6268   -0.2042    0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7979   -1.4797    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6444   -1.1653    1.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4981   -1.7905    0.7030 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4007   -0.2828    1.4073 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6023   -1.0642    1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5122   -0.5002    0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8075   -0.0007    0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8026    0.6037   -0.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4612    0.0743   -1.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6534   -1.1573   -1.8816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0966   -0.2541    0.7791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7562   -0.5986    0.7347 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1263    0.4654    0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1421    1.2940    1.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4817   -0.1627    1.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3511   -0.9311    2.2501 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983    0.7752    1.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8355   -0.0264    1.6389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9447    0.7243    0.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3799   -0.0445   -0.1349 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6150    0.4809   -0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0895   -0.2160   -1.7661 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1966   -1.1228   -1.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2999   -0.8466    0.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7673   -2.0293    0.9147 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8304   -3.0038    1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1138   -2.8153    1.0018 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5071   -1.5601    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8440   -1.0614    0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9548   -1.4866    0.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3275   -1.0760    0.5498 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3821   -0.0639    1.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7165    1.1998    1.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2337    1.3887    0.0703 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5793    2.2638    2.1139 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6086   -0.5473    0.5370 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5341    0.2467    0.4463 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3996    1.9656   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2034    2.5213   -1.8866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9297    2.3190   -0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2473    1.9712    0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9123    1.6243    0.2679 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0126    1.2558   -0.4046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5579    0.4875   -1.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3823    1.6804   -0.6567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4457    1.0509    0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8265    2.0667    1.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2173   -2.0111   -0.8263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -3.1313   -0.8668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1993   -1.9443    1.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3892   -2.9207    0.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656   -0.8687   -1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8696   -1.7785   -1.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0740    0.0532   -2.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8600    0.1603   -3.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4917    1.5973   -2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9796    1.6258   -3.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6101    2.2562   -0.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3510    1.9510   -0.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2896    1.8834    1.4223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9755    0.6204    2.1887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3562   -2.3737    0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5031   -1.5646   -0.9792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9969   -1.6060    1.9935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8244   -0.7175    2.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3851   -2.1195    1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1364   -1.0565    2.2133 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8098   -1.2694   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0692   -0.7381    1.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.6202    0.0267    0.0659 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6740    0.9682    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5716    1.4009    0.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3608    0.9934   -1.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0305    0.8634   -1.6734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9283   -1.1697   -2.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7172   -2.0887   -1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6688   -1.0386   -2.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3074   -0.2033    1.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5286    0.8170    2.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6722   -0.8885    0.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4004   -0.2665    3.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4177    1.4250    2.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9970   -0.0875    2.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241217562D          

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M  END
> <DATABASE_ID>
HMDB0033805

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CNC2(CC3OC4(CC(=C)C5OC(O)(C(O)C6CC7OC8(CCC9(CC=CC(O9)\C=C\CCC(O)=O)O8)C(C)CC7O6)C(C)CC5C)CC(C)CC(O4)C3O2)C(C)C1

> <INCHI_IDENTIFIER>
InChI=1S/C47H71NO12/c1-26-18-36-41-38(24-45(58-41)30(5)17-27(2)25-48-45)56-44(22-26,55-36)23-29(4)40-28(3)19-32(7)47(52,59-40)42(51)37-21-35-34(53-37)20-31(6)46(57-35)16-15-43(60-46)14-10-12-33(54-43)11-8-9-13-39(49)50/h8,10-12,26-28,30-38,40-42,48,51-52H,4,9,13-25H2,1-3,5-7H3,(H,49,50)/b11-8+

> <INCHI_KEY>
BVZWTQCTAVYACS-DHZHZOJOSA-N

> <FORMULA>
C47H71NO12

> <MOLECULAR_WEIGHT>
842.0661

> <EXACT_MASS>
841.497626741

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
94.20855505247148

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4E)-5-(2-{hydroxy[2-hydroxy-3,5-dimethyl-6-(3-{3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0²,⁶]dodecane]-8'-yl}prop-1-en-2-yl)oxan-2-yl]methyl}-6-methyl-2,3,3'',3a,6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl)pent-4-enoic acid

> <ALOGPS_LOGP>
3.71

> <JCHEM_LOGP>
4.724207758980684

> <ALOGPS_LOGS>
-5.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.868226798339737

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9547511647299527

> <JCHEM_PKA_STRONGEST_BASIC>
9.319417479833277

> <JCHEM_POLAR_SURFACE_AREA>
163.63

> <JCHEM_REFRACTIVITY>
221.91650000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.86e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4E)-5-(2-{hydroxy[2-hydroxy-3,5-dimethyl-6-(3-{3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0²,⁶]dodecane]-8'-yl}prop-1-en-2-yl)oxan-2-yl]methyl}-6-methyl-2,3,3'',3a,6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl)pent-4-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033805
     RDKit          3D
Azaspiracid
131139  0  0  0  0  0  0  0  0999 V2000
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   -2.8722   -1.4399    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2146   -1.8505    0.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3884   -0.9888    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4123   -0.8348   -1.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0797    0.3704   -1.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3229    0.9789   -2.8329 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.3313    0.1491    1.0908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6762    0.2999    1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6791    0.8087    0.3235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6268   -0.2042    0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.879   4.793   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.879   3.253   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.211   2.483   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.541   3.253   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.541   4.793   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.211   5.560   0.000  0.00  0.00           O+0
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HETATM   45  O   UNK     0       4.049  -1.556   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       1.739  -2.891   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.509  -1.556   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.474  -0.412   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.063  -1.043   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       0.224  -2.583   0.000  0.00  0.00           O+0
HETATM   51  N   UNK     0       0.063   0.497   0.000  0.00  0.00           N+0
HETATM   52  C   UNK     0      -1.271   1.266   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -2.606   0.497   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -2.606  -1.043   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -1.271  -1.813   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       5.904  -6.649   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      -1.271  -3.353   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -3.941   1.266   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       6.728   2.296   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -0.455   2.483   0.000  0.00  0.00           C+0
CONECT    1    2    6    7   10                                             
CONECT    2    1    3   60                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6   18                                                  
CONECT    6    1    5                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   15                                             
CONECT   10    1    9                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15    9   14                                                       
CONECT   16    4   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18    5   17                                                       
CONECT   19   14   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   17   27   28                                                  
CONECT   27   26   29   33   59                                             
CONECT   28   26                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31   36                                                  
CONECT   31   30   32   35                                                  
CONECT   32   31   33                                                       
CONECT   33   27   32   34                                                  
CONECT   34   33                                                            
CONECT   35   31                                                            
CONECT   36   30   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   44   45                                             
CONECT   40   39   41                                                       
CONECT   41   40   42   46                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   56                                                  
CONECT   44   39   43                                                       
CONECT   45   39   47                                                       
CONECT   46   41   47   50                                                  
CONECT   47   45   46   48                                                  
CONECT   48   47   49                                                       
CONECT   49   48   50   51   55                                             
CONECT   50   46   49                                                       
CONECT   51   49   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54   58                                                  
CONECT   54   53   55                                                       
CONECT   55   49   54   57                                                  
CONECT   56   43                                                            
CONECT   57   55                                                            
CONECT   58   53                                                            
CONECT   59   27                                                            
CONECT   60    2                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  136    0
END

COMPND    HMDB0033805
HETATM    1  C1  UNL     1      -2.202  -2.252  -0.515  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.872  -1.440   0.347  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.215  -1.851   0.716  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.388  -0.989   0.351  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.412  -0.835  -1.140  1.00  0.00           C  
HETATM    6  C6  UNL     1      -6.080   0.370  -1.661  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.323   0.979  -2.833  1.00  0.00           C  
HETATM    8  C8  UNL     1      -6.377   1.444  -0.664  1.00  0.00           C  
HETATM    9  C9  UNL     1      -6.386   0.984   0.756  1.00  0.00           C  
HETATM   10  O1  UNL     1      -5.331   0.149   1.091  1.00  0.00           O  
HETATM   11  C10 UNL     1      -7.676   0.300   1.146  1.00  0.00           C  
HETATM   12  O2  UNL     1      -8.679   0.809   0.323  1.00  0.00           O  
HETATM   13  C11 UNL     1      -9.627  -0.204   0.201  1.00  0.00           C  
HETATM   14  C12 UNL     1      -8.798  -1.480   0.068  1.00  0.00           C  
HETATM   15  C13 UNL     1      -7.644  -1.165   1.006  1.00  0.00           C  
HETATM   16  O3  UNL     1      -6.498  -1.790   0.703  1.00  0.00           O  
HETATM   17  N1  UNL     1     -10.401  -0.283   1.407  1.00  0.00           N  
HETATM   18  C14 UNL     1     -11.602  -1.064   1.246  1.00  0.00           C  
HETATM   19  C15 UNL     1     -12.512  -0.500   0.184  1.00  0.00           C  
HETATM   20  C16 UNL     1     -13.808  -0.001   0.813  1.00  0.00           C  
HETATM   21  C17 UNL     1     -11.803   0.604  -0.529  1.00  0.00           C  
HETATM   22  C18 UNL     1     -10.461   0.074  -1.017  1.00  0.00           C  
HETATM   23  C19 UNL     1     -10.653  -1.157  -1.882  1.00  0.00           C  
HETATM   24  C20 UNL     1      -2.097  -0.254   0.779  1.00  0.00           C  
HETATM   25  O4  UNL     1      -0.756  -0.599   0.735  1.00  0.00           O  
HETATM   26  C21 UNL     1       0.126   0.465   0.857  1.00  0.00           C  
HETATM   27  O5  UNL     1      -0.142   1.294   1.942  1.00  0.00           O  
HETATM   28  C22 UNL     1       1.482  -0.163   1.068  1.00  0.00           C  
HETATM   29  O6  UNL     1       1.351  -0.931   2.250  1.00  0.00           O  
HETATM   30  C23 UNL     1       2.598   0.775   1.289  1.00  0.00           C  
HETATM   31  C24 UNL     1       3.835  -0.026   1.639  1.00  0.00           C  
HETATM   32  C25 UNL     1       4.945   0.724   0.943  1.00  0.00           C  
HETATM   33  O7  UNL     1       5.380  -0.045  -0.135  1.00  0.00           O  
HETATM   34  C26 UNL     1       6.615   0.481  -0.538  1.00  0.00           C  
HETATM   35  C27 UNL     1       7.090  -0.216  -1.766  1.00  0.00           C  
HETATM   36  C28 UNL     1       8.197  -1.123  -1.318  1.00  0.00           C  
HETATM   37  C29 UNL     1       8.300  -0.847   0.145  1.00  0.00           C  
HETATM   38  C30 UNL     1       7.767  -2.029   0.915  1.00  0.00           C  
HETATM   39  C31 UNL     1       8.830  -3.004   1.270  1.00  0.00           C  
HETATM   40  C32 UNL     1      10.114  -2.815   1.002  1.00  0.00           C  
HETATM   41  C33 UNL     1      10.507  -1.560   0.309  1.00  0.00           C  
HETATM   42  C34 UNL     1      11.844  -1.061   0.773  1.00  0.00           C  
HETATM   43  C35 UNL     1      12.955  -1.487   0.194  1.00  0.00           C  
HETATM   44  C36 UNL     1      14.328  -1.076   0.550  1.00  0.00           C  
HETATM   45  C37 UNL     1      14.382  -0.064   1.637  1.00  0.00           C  
HETATM   46  C38 UNL     1      13.717   1.200   1.234  1.00  0.00           C  
HETATM   47  O8  UNL     1      13.234   1.389   0.070  1.00  0.00           O  
HETATM   48  O9  UNL     1      13.579   2.264   2.114  1.00  0.00           O  
HETATM   49  O10 UNL     1       9.609  -0.547   0.537  1.00  0.00           O  
HETATM   50  O11 UNL     1       7.534   0.247   0.446  1.00  0.00           O  
HETATM   51  C39 UNL     1       6.400   1.966  -0.754  1.00  0.00           C  
HETATM   52  C40 UNL     1       7.203   2.521  -1.887  1.00  0.00           C  
HETATM   53  C41 UNL     1       4.930   2.319  -0.882  1.00  0.00           C  
HETATM   54  C42 UNL     1       4.247   1.971   0.420  1.00  0.00           C  
HETATM   55  O12 UNL     1       2.912   1.624   0.268  1.00  0.00           O  
HETATM   56  C43 UNL     1       0.013   1.256  -0.405  1.00  0.00           C  
HETATM   57  C44 UNL     1       0.558   0.487  -1.607  1.00  0.00           C  
HETATM   58  C45 UNL     1      -1.382   1.680  -0.657  1.00  0.00           C  
HETATM   59  C46 UNL     1      -2.446   1.051   0.220  1.00  0.00           C  
HETATM   60  C47 UNL     1      -2.826   2.067   1.310  1.00  0.00           C  
HETATM   61  H1  UNL     1      -1.217  -2.011  -0.826  1.00  0.00           H  
HETATM   62  H2  UNL     1      -2.690  -3.131  -0.867  1.00  0.00           H  
HETATM   63  H3  UNL     1      -4.199  -1.944   1.861  1.00  0.00           H  
HETATM   64  H4  UNL     1      -4.389  -2.921   0.416  1.00  0.00           H  
HETATM   65  H5  UNL     1      -4.366  -0.869  -1.568  1.00  0.00           H  
HETATM   66  H6  UNL     1      -5.870  -1.778  -1.554  1.00  0.00           H  
HETATM   67  H7  UNL     1      -7.074   0.053  -2.097  1.00  0.00           H  
HETATM   68  H8  UNL     1      -4.860   0.160  -3.412  1.00  0.00           H  
HETATM   69  H9  UNL     1      -4.492   1.597  -2.438  1.00  0.00           H  
HETATM   70  H10 UNL     1      -5.980   1.626  -3.447  1.00  0.00           H  
HETATM   71  H11 UNL     1      -5.610   2.256  -0.743  1.00  0.00           H  
HETATM   72  H12 UNL     1      -7.351   1.951  -0.854  1.00  0.00           H  
HETATM   73  H13 UNL     1      -6.290   1.883   1.422  1.00  0.00           H  
HETATM   74  H14 UNL     1      -7.976   0.620   2.189  1.00  0.00           H  
HETATM   75  H15 UNL     1      -9.356  -2.374   0.349  1.00  0.00           H  
HETATM   76  H16 UNL     1      -8.503  -1.565  -0.979  1.00  0.00           H  
HETATM   77  H17 UNL     1      -7.997  -1.606   1.994  1.00  0.00           H  
HETATM   78  H18 UNL     1      -9.824  -0.718   2.148  1.00  0.00           H  
HETATM   79  H19 UNL     1     -11.385  -2.120   1.011  1.00  0.00           H  
HETATM   80  H20 UNL     1     -12.136  -1.057   2.213  1.00  0.00           H  
HETATM   81  H21 UNL     1     -12.810  -1.269  -0.557  1.00  0.00           H  
HETATM   82  H22 UNL     1     -14.069  -0.738   1.599  1.00  0.00           H  
HETATM   83  H23 UNL     1     -14.620   0.027   0.066  1.00  0.00           H  
HETATM   84  H24 UNL     1     -13.674   0.968   1.313  1.00  0.00           H  
HETATM   85  H25 UNL     1     -11.572   1.401   0.209  1.00  0.00           H  
HETATM   86  H26 UNL     1     -12.361   0.993  -1.403  1.00  0.00           H  
HETATM   87  H27 UNL     1     -10.030   0.863  -1.673  1.00  0.00           H  
HETATM   88  H28 UNL     1      -9.928  -1.170  -2.698  1.00  0.00           H  
HETATM   89  H29 UNL     1     -10.717  -2.089  -1.294  1.00  0.00           H  
HETATM   90  H30 UNL     1     -11.669  -1.039  -2.356  1.00  0.00           H  
HETATM   91  H31 UNL     1      -2.307  -0.203   1.911  1.00  0.00           H  
HETATM   92  H32 UNL     1      -0.529   0.817   2.706  1.00  0.00           H  
HETATM   93  H33 UNL     1       1.672  -0.888   0.258  1.00  0.00           H  
HETATM   94  H34 UNL     1       1.400  -0.267   3.007  1.00  0.00           H  
HETATM   95  H35 UNL     1       2.418   1.425   2.197  1.00  0.00           H  
HETATM   96  H36 UNL     1       3.720  -1.044   1.215  1.00  0.00           H  
HETATM   97  H37 UNL     1       3.997  -0.087   2.738  1.00  0.00           H  
HETATM   98  H38 UNL     1       5.741   0.957   1.655  1.00  0.00           H  
HETATM   99  H39 UNL     1       6.256  -0.823  -2.229  1.00  0.00           H  
HETATM  100  H40 UNL     1       7.509   0.457  -2.545  1.00  0.00           H  
HETATM  101  H41 UNL     1       9.164  -0.899  -1.842  1.00  0.00           H  
HETATM  102  H42 UNL     1       7.936  -2.171  -1.561  1.00  0.00           H  
HETATM  103  H43 UNL     1       7.328  -1.671   1.867  1.00  0.00           H  
HETATM  104  H44 UNL     1       6.980  -2.540   0.326  1.00  0.00           H  
HETATM  105  H45 UNL     1       8.543  -3.909   1.770  1.00  0.00           H  
HETATM  106  H46 UNL     1      10.883  -3.544   1.270  1.00  0.00           H  
HETATM  107  H47 UNL     1      10.626  -1.821  -0.763  1.00  0.00           H  
HETATM  108  H48 UNL     1      11.883  -0.362   1.596  1.00  0.00           H  
HETATM  109  H49 UNL     1      12.810  -2.211  -0.624  1.00  0.00           H  
HETATM  110  H50 UNL     1      14.782  -0.629  -0.359  1.00  0.00           H  
HETATM  111  H51 UNL     1      14.893  -2.008   0.816  1.00  0.00           H  
HETATM  112  H52 UNL     1      15.456   0.157   1.843  1.00  0.00           H  
HETATM  113  H53 UNL     1      13.886  -0.411   2.573  1.00  0.00           H  
HETATM  114  H54 UNL     1      12.816   2.928   2.066  1.00  0.00           H  
HETATM  115  H55 UNL     1       6.759   2.464   0.180  1.00  0.00           H  
HETATM  116  H56 UNL     1       8.255   2.193  -1.783  1.00  0.00           H  
HETATM  117  H57 UNL     1       6.771   2.325  -2.888  1.00  0.00           H  
HETATM  118  H58 UNL     1       7.175   3.644  -1.770  1.00  0.00           H  
HETATM  119  H59 UNL     1       4.892   3.424  -0.999  1.00  0.00           H  
HETATM  120  H60 UNL     1       4.453   1.877  -1.761  1.00  0.00           H  
HETATM  121  H61 UNL     1       4.366   2.780   1.147  1.00  0.00           H  
HETATM  122  H62 UNL     1       0.649   2.192  -0.374  1.00  0.00           H  
HETATM  123  H63 UNL     1       0.603  -0.588  -1.447  1.00  0.00           H  
HETATM  124  H64 UNL     1      -0.161   0.640  -2.467  1.00  0.00           H  
HETATM  125  H65 UNL     1       1.520   0.862  -1.967  1.00  0.00           H  
HETATM  126  H66 UNL     1      -1.507   2.792  -0.554  1.00  0.00           H  
HETATM  127  H67 UNL     1      -1.609   1.509  -1.751  1.00  0.00           H  
HETATM  128  H68 UNL     1      -3.329   0.965  -0.436  1.00  0.00           H  
HETATM  129  H69 UNL     1      -2.835   1.614   2.314  1.00  0.00           H  
HETATM  130  H70 UNL     1      -3.858   2.455   1.156  1.00  0.00           H  
HETATM  131  H71 UNL     1      -2.174   2.959   1.217  1.00  0.00           H  
CONECT    1    2    2   61   62
CONECT    2    3   24
CONECT    3    4   63   64
CONECT    4    5   10   16
CONECT    5    6   65   66
CONECT    6    7    8   67
CONECT    7   68   69   70
CONECT    8    9   71   72
CONECT    9   10   11   73
CONECT   11   12   15   74
CONECT   12   13
CONECT   13   14   17   22
CONECT   14   15   75   76
CONECT   15   16   77
CONECT   17   18   78
CONECT   18   19   79   80
CONECT   19   20   21   81
CONECT   20   82   83   84
CONECT   21   22   85   86
CONECT   22   23   87
CONECT   23   88   89   90
CONECT   24   25   59   91
CONECT   25   26
CONECT   26   27   28   56
CONECT   27   92
CONECT   28   29   30   93
CONECT   29   94
CONECT   30   31   55   95
CONECT   31   32   96   97
CONECT   32   33   54   98
CONECT   33   34
CONECT   34   35   50   51
CONECT   35   36   99  100
CONECT   36   37  101  102
CONECT   37   38   49   50
CONECT   38   39  103  104
CONECT   39   40   40  105
CONECT   40   41  106
CONECT   41   42   49  107
CONECT   42   43   43  108
CONECT   43   44  109
CONECT   44   45  110  111
CONECT   45   46  112  113
CONECT   46   47   47   48
CONECT   48  114
CONECT   51   52   53  115
CONECT   52  116  117  118
CONECT   53   54  119  120
CONECT   54   55  121
CONECT   56   57   58  122
CONECT   57  123  124  125
CONECT   58   59  126  127
CONECT   59   60  128
CONECT   60  129  130  131
END

HMDB0033805
     RDKit          3D
Azaspiracid
131139  0  0  0  0  0  0  0  0999 V2000
   -2.2022   -2.2519   -0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8722   -1.4399    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2146   -1.8505    0.7159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3884   -0.9888    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4123   -0.8348   -1.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0797    0.3704   -1.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3229    0.9789   -2.8329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3773    1.4441   -0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3855    0.9839    0.7561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3313    0.1491    1.0908 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6762    0.2999    1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6791    0.8087    0.3235 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6268   -0.2042    0.2014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7979   -1.4797    0.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6444   -1.1653    1.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4981   -1.7905    0.7030 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4007   -0.2828    1.4073 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6023   -1.0642    1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Azaspiracid-1	HMDB
(4E)-5-(2-{hydroxy[2-hydroxy-3,5-dimethyl-6-(3-{3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0²,⁶]dodecane]-8'-yl}prop-1-en-2-yl)oxan-2-yl]methyl}-6-methyl-2,3,3'',3a,6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl)pent-4-enoate	Generator

Chemical Formula

C₄₇H₇₁NO₁₂

Average Molecular Weight

842.0661

Monoisotopic Molecular Weight

841.497626741

IUPAC Name

(4E)-5-(2-{hydroxy[2-hydroxy-3,5-dimethyl-6-(3-{3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0²,⁶]dodecane]-8'-yl}prop-1-en-2-yl)oxan-2-yl]methyl}-6-methyl-2,3,3'',3a,6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl)pent-4-enoic acid

Traditional Name

CAS Registry Number

214899-21-5

SMILES

CC1CNC2(CC3OC4(CC(=C)C5OC(O)(C(O)C6CC7OC8(CCC9(CC=CC(O9)\C=C\CCC(O)=O)O8)C(C)CC7O6)C(C)CC5C)CC(C)CC(O4)C3O2)C(C)C1

InChI Identifier

InChI=1S/C47H71NO12/c1-26-18-36-41-38(24-45(58-41)30(5)17-27(2)25-48-45)56-44(22-26,55-36)23-29(4)40-28(3)19-32(7)47(52,59-40)42(51)37-21-35-34(53-37)20-31(6)46(57-35)16-15-43(60-46)14-10-12-33(54-43)11-8-9-13-39(49)50/h8,10-12,26-28,30-38,40-42,48,51-52H,4,9,13-25H2,1-3,5-7H3,(H,49,50)/b11-8+

InChI Key

BVZWTQCTAVYACS-DHZHZOJOSA-N

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
Furopyran
Medium-chain fatty acid
Amino fatty acid
Ketal
Heterocyclic fatty acid
Hydroxy fatty acid
Meta-dioxane
Monosaccharide
Oxane
Piperidine
Pyran
Unsaturated fatty acid
Fatty acid
Fatty acyl
Tetrahydrofuran
Furan
Secondary alcohol
Amino acid or derivatives
Hemiacetal
Hemiaminal
Amino acid
Oxacycle
Azacycle
Secondary amine
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Secondary aliphatic amine
Ether
Acetal
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Amine
Organic oxygen compound
Alcohol
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Carbonyl group
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

golgi apparatus (HMDB: HMDB0033805)

Cell membrane (HMDB: HMDB0033805)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033805)

Source

Endogenous

Endogenous (HMDB: HMDB0033805)

Animal

Animal (HMDB: HMDB0033805)

Exogenous

Food

Food (HMDB: HMDB0033805)

Aquatic origin

Mollusk

Mollusks (FooDB: FOOD00868)

Process

Naturally occurring process

Biological process

Biochemical pathway

Signaling pathway

Apoptosis (HMDB: HMDB0033805)

Cellular process

Apoptosis (HMDB: HMDB0033805)
Cell signaling (HMDB: HMDB0033805)

Biochemical process

Endocytosis (HMDB: HMDB0033805)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0033805)

Nutrient

Nutrient (HMDB: HMDB0033805)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033805)

Emulsifier (HMDB: HMDB0033805)

Indirect biological role

Marine biotoxin (HMDB: HMDB0033805)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0019 g/L	ALOGPS
logP	3.71	ALOGPS
logP	4.72	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	3.95	ChemAxon
pKa (Strongest Basic)	9.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	163.63 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	221.92 m³·mol⁻¹	ChemAxon
Polarizability	94.21 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	278.7	32859911
AllCCS	[M+H-H2O]+	278.2	32859911
AllCCS	[M+NH4]+	279.2	32859911
AllCCS	[M+Na]+	279.4	32859911
AllCCS	[M-H]-	290.6	32859911
AllCCS	[M+Na-2H]-	297.9	32859911
AllCCS	[M+HCOO]-	305.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Azaspiracid	CC1CNC2(CC3OC4(CC(=C)C5OC(O)(C(O)C6CC7OC8(CCC9(CC=CC(O9)\C=C\CCC(O)=O)O8)C(C)CC7O6)C(C)CC5C)CC(C)CC(O4)C3O2)C(C)C1	5177.3	Standard polar	33892256
Azaspiracid	CC1CNC2(CC3OC4(CC(=C)C5OC(O)(C(O)C6CC7OC8(CCC9(CC=CC(O9)\C=C\CCC(O)=O)O8)C(C)CC7O6)C(C)CC5C)CC(C)CC(O4)C3O2)C(C)C1	4769.1	Standard non polar	33892256
Azaspiracid	CC1CNC2(CC3OC4(CC(=C)C5OC(O)(C(O)C6CC7OC8(CCC9(CC=CC(O9)\C=C\CCC(O)=O)O8)C(C)CC7O6)C(C)CC5C)CC(C)CC(O4)C3O2)C(C)C1	5534.6	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azaspiracid 10V, Negative-QTOF	splash10-002b-2822892050-8005cf406abf6110e930	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azaspiracid 20V, Negative-QTOF	splash10-074j-0296322350-59fbc3408ecbeb977cfc	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azaspiracid 40V, Negative-QTOF	splash10-066r-1910000000-f56c2be33379f3a85c38	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azaspiracid 10V, Negative-QTOF	splash10-0006-0002000090-d45bf0369df4637bb58c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azaspiracid 20V, Negative-QTOF	splash10-0006-1009500060-b12bb23fe395a67ac201	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azaspiracid 40V, Negative-QTOF	splash10-00di-0904001330-52022d8ec6d1694f0263	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azaspiracid 10V, Positive-QTOF	splash10-00di-1409310060-798e0b2f824d8853730a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azaspiracid 20V, Positive-QTOF	splash10-001i-6609021000-1dbcf3bdba6d54e1b8ec	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azaspiracid 40V, Positive-QTOF	splash10-00fr-4901000000-1276d3ab3d40e7e96b73	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azaspiracid 10V, Positive-QTOF	splash10-006x-0000000090-09ceb2dfdd4b844ee6b8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azaspiracid 20V, Positive-QTOF	splash10-00dl-0023200090-2795366f5d1d56c6f679	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Azaspiracid 40V, Positive-QTOF	splash10-0a4i-7490000010-51bbecbe9652f88306d1	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011968

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Azaspiracid

METLIN ID

Not Available

PubChem Compound

131751490

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

These A, Scholz J, Preiss-Weigert A: Sensitive method for the determination of lipophilic marine biotoxins in extracts of mussels and processed shellfish by high-performance liquid chromatography-tandem mass spectrometry based on enrichment by solid-phase extraction. J Chromatogr A. 2009 May 22;1216(21):4529-38. doi: 10.1016/j.chroma.2009.03.062. Epub 2009 Mar 27. [PubMed:19362722 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Azaspiracid (HMDB0033805)

MOL for HMDB0033805 (Azaspiracid)

3D MOL for HMDB0033805 (Azaspiracid)

3D SDF for HMDB0033805 (Azaspiracid)

3D-SDF for HMDB0033805 (Azaspiracid)

PDB for HMDB0033805 (Azaspiracid)

3D PDB for HMDB0033805 (Azaspiracid)

SMILES for HMDB0033805 (Azaspiracid)

INCHI for HMDB0033805 (Azaspiracid)

Structure for HMDB0033805 (Azaspiracid)

3D Structure for HMDB0033805 (Azaspiracid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra