NP-MRD: Showing NP-Card for (2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid (NP0288982)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-09 18:56:59 UTC

Updated at

2022-09-09 18:56:59 UTC

NP-MRD ID

NP0288982

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid

Description

Calbistrin D belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid is found in Penicillium restrictum. Based on a literature review very few articles have been published on Calbistrin D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092220572D          

 39 40  0  0  1  0            999 V2000
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3895   -1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3289   -1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3322   -0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625   -1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3928   -2.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0501   -1.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5198   -1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7073   -1.2548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  1  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 26 33  1  0  0  0  0
 33 20  1  1  0  0  0
 15 33  1  0  0  0  0
  2 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
M  END

     RDKit          3D

 81 82  0  0  0  0  0  0  0  0999 V2000
    6.3061   -2.4039    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8054   -1.8521    1.7315 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9305   -0.7578    1.7738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3026   -0.3368    0.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4386    0.6907    0.5432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7601    0.8155   -0.7348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -0.2034   -1.7136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8118    1.7159   -1.1425 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1714    2.2846   -2.4036 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9282    2.6376   -0.3878 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6214    2.2026    1.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4368    2.3013   -1.1821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7708    3.1730   -1.9631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0212    1.1431   -0.9381 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0623    0.4343   -1.4868 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3270   -0.9834   -1.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9819   -1.2560   -0.1695 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2385   -1.9913    0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1886   -1.5998    0.5608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2840   -0.9615    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5583   -1.2633    0.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6902   -0.6964    0.5392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6798    0.2791   -0.5989 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8119   -0.5461   -1.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7987    1.1106   -0.5350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3642    1.0372   -0.5336 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2052    1.4502    0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3890    2.2572   -1.3355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7619    2.4169   -2.4030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1960    3.4273   -0.9341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0699    4.5328   -2.0079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8163    5.6304   -1.6402 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3075    0.0296   -0.8680 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3949   -2.4145    2.8752 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2098   -3.4262    2.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5150   -3.7856    4.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3743   -4.8562    4.5968 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6448   -5.2343    5.7381 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9855   -5.5911    3.5385 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6609   -1.5601   -0.2651 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5416   -2.9514   -0.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2756   -2.9621    0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6570   -0.1713    2.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7085   -0.9649   -0.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2835    1.7578    0.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6771   -0.1445   -2.6646 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2818   -1.2206   -1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3105    0.0568   -2.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008    0.9124   -1.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1410    2.5357   -2.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1560    3.6616   -0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421    2.4955    1.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2461    2.8272    1.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660    1.1624    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360    0.8362   -2.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0523   -1.6806   -2.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4115   -0.8591   -2.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7738   -0.1644    0.2749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2414   -3.0842    0.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0973   -1.6241   -0.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6460   -1.7194    1.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1904   -2.3160    1.3484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5730   -1.9736    1.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6277   -0.9263    1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9198   -0.5332   -2.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3284   -0.1362   -2.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5994   -1.6090   -1.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4567    0.8560   -1.2407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6616    2.4411    0.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5466    0.7723    1.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1882    1.6535    1.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2838    3.1873   -0.9453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8699    3.9024    0.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0143    4.8311   -2.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4688    4.1501   -2.9870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6116    5.4234   -1.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7934   -0.6274   -1.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9303   -1.8394    3.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8768   -4.2939    2.5467 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0260   -3.1498    4.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4061   -6.3615    3.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  6  1  0
  6  7  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
  2 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 39  1  0
 37 38  2  0
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  1  1
 23 26  1  0
 26 27  1  0
 26 33  1  0
 26 28  1  6
 28 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 33 15  1  0
 33 20  1  0
 11 52  1  0
 11 53  1  0
 11 54  1  0
 10 51  1  1
  8 49  1  6
  9 50  1  0
  7 46  1  0
  7 47  1  0
  7 48  1  0
  5 45  1  0
  4 44  1  0
  3 43  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
 34 78  1  0
 35 79  1  0
 36 80  1  0
 39 81  1  0
 15 55  1  6
 16 56  1  0
 16 57  1  0
 17 58  1  1
 18 59  1  0
 18 60  1  0
 18 61  1  0
 19 62  1  0
 21 63  1  0
 22 64  1  0
 24 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 33 77  1  6
 30 72  1  0
 30 73  1  0
 31 74  1  0
 31 75  1  0
 32 76  1  0
M  END


  Mrv1652309092220572D          

 39 40  0  0  1  0            999 V2000
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.3895   -1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3289   -1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3322   -0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8625   -1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3928   -2.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0501   -1.7435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5198   -1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7073   -1.2548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  1  0  0  0
 23 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  6  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 26 33  1  0  0  0  0
 33 20  1  1  0  0  0
 15 33  1  0  0  0  0
  2 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288982

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C(O)C(\C)=C\C=C\C(\C)=C\C=C\C(O)=O)C(=O)O[C@H]1C[C@H](C)C=C2C=C[C@@](C)(O)[C@@](C)([C@@H]12)C(=O)CCO

> <INCHI_IDENTIFIER>
InChI=1S/C31H42O8/c1-19(10-8-12-26(34)35)9-7-11-21(3)28(36)22(4)29(37)39-24-18-20(2)17-23-13-15-30(5,38)31(6,27(23)24)25(33)14-16-32/h7-13,15,17,20,22,24,27-28,32,36,38H,14,16,18H2,1-6H3,(H,34,35)/b9-7+,12-8+,19-10+,21-11+/t20-,22?,24+,27-,28?,30-,31-/m1/s1

> <INCHI_KEY>
VBTJSQZQYFMROV-MQYQVPAESA-N

> <FORMULA>
C31H42O8

> <MOLECULAR_WEIGHT>
542.669

> <EXACT_MASS>
542.287968312

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
59.8966981390156

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E,4E,6E,8E)-12-{[(1S,3S,7R,8R,8aS)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid

> <JCHEM_LOGP>
3.3008380726666653

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.727094591684615

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.686167045791492

> <JCHEM_PKA_STRONGEST_BASIC>
-2.441169869882337

> <JCHEM_POLAR_SURFACE_AREA>
141.36

> <JCHEM_REFRACTIVITY>
154.69990000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,6E,8E)-12-{[(1S,3S,7R,8R,8aS)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.670   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.004   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.004  -1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      15.660  -3.490   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.681  -3.490   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.820  -1.273   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.810  -2.987   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      13.800  -4.167   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.293  -3.255   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.304  -2.075   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       8.787  -2.342   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -6.668   0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   33                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27   28   33                                             
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   26   20   15                                                  
CONECT   34    2   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₄₂O₈

Average Mass

542.6690 Da

Monoisotopic Mass

542.28797 Da

IUPAC Name

(2E,4E,6E,8E)-12-{[(1S,3S,7R,8R,8aS)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid

Traditional Name

(2E,4E,6E,8E)-12-{[(1S,3S,7R,8R,8aS)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid

CAS Registry Number

Not Available

SMILES

CC(C(O)C(\C)=C\C=C\C(\C)=C\C=C\C(O)=O)C(=O)O[C@H]1C[C@H](C)C=C2C=C[C@@](C)(O)[C@@](C)([C@@H]12)C(=O)CCO

InChI Identifier

InChI=1S/C31H42O8/c1-19(10-8-12-26(34)35)9-7-11-21(3)28(36)22(4)29(37)39-24-18-20(2)17-23-13-15-30(5,38)31(6,27(23)24)25(33)14-16-32/h7-13,15,17,20,22,24,27-28,32,36,38H,14,16,18H2,1-6H3,(H,34,35)/b9-7+,12-8+,19-10+,21-11+/t20-,22?,24+,27-,28?,30-,31-/m1/s1

InChI Key

VBTJSQZQYFMROV-MQYQVPAESA-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
Penicillium restrictum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Medium-chain hydroxy acid
Medium-chain fatty acid
Beta-hydroxy acid
Branched fatty acid
Fatty acid ester
Hydroxy fatty acid
Beta-hydroxy ketone
Fatty acyl
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Hydroxy acid
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Ketone
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Primary alcohol
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.3	ChemAxon
pKa (Strongest Acidic)	4.69	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	154.7 m³·mol⁻¹	ChemAxon
Polarizability	59.9 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

8251559

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10076021

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid (NP0288982)

MOL for NP0288982 ((2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid)

3D MOL for NP0288982 ((2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid)

3D SDF for NP0288982 ((2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid)

3D-SDF for NP0288982 ((2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid)

PDB for NP0288982 ((2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid)

3D PDB for NP0288982 ((2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid)

SMILES for NP0288982 ((2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid)

INCHI for NP0288982 ((2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid)

Structure for NP0288982 ((2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid)

3D Structure for NP0288982 ((2e,4e,6e,8e)-12-{[(1s,3s,7r,8r,8as)-7-hydroxy-8-(3-hydroxypropanoyl)-3,7,8-trimethyl-1,2,3,8a-tetrahydronaphthalen-1-yl]oxy}-10-hydroxy-5,9,11-trimethyl-12-oxododeca-2,4,6,8-tetraenoic acid)