NP-MRD: Showing NP-Card for (2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol (NP0167497)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-03 03:05:14 UTC

Updated at

2022-09-03 03:05:14 UTC

NP-MRD ID

NP0167497

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol

Description

Aplysqualenol B belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol is found in Aplysia dactylomela. (2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol was first documented in 2009 (PMID: 23459021). Based on a literature review very few articles have been published on Aplysqualenol B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032205052D          

 40 43  0  0  1  0            999 V2000
    7.6431   -3.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6431   -4.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9286   -4.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2142   -4.3098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3576   -4.7223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0720   -4.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7865   -4.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7865   -5.5473    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9660   -5.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6070   -5.4610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9426   -6.2147    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7495   -6.3862    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5780   -7.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9211   -5.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5565   -6.5578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1085   -5.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9155   -6.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1704   -6.9008    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.9774   -7.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2324   -7.8570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0393   -8.0285    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7303   -8.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0681   -7.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7965   -6.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4962   -7.2539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2246   -6.8665    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.4674   -8.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2844   -7.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7223   -8.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7390   -8.4657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6803   -8.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8733   -8.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6184   -7.5139    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0664   -8.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8114   -7.3424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3295   -6.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6150   -6.3542    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8613   -6.6898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3576   -5.5473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6431   -5.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  1  0  0  0
 12 14  1  1  0  0  0
 15 12  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 21 30  1  6  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 15 35  1  0  0  0  0
 11 36  1  0  0  0  0
 36 37  1  0  0  0  0
  8 37  1  0  0  0  0
 37 38  1  1  0  0  0
  5 39  1  1  0  0  0
 39 40  1  0  0  0  0
M  END

     RDKit          3D

 93 96  0  0  0  0  0  0  0  0999 V2000
   -7.3256   -2.0675   -1.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9081   -1.2186   -0.2308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0242   -1.7786    0.6292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2137   -3.1298    0.3840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6297    0.2406   -0.1212 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3477    0.6503   -0.8290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1991    0.0386   -0.0595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8512    0.3444   -0.6755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7853   -0.1905   -2.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8950   -0.3300    0.0722 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6505    0.5219    1.1355 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3639    0.2336    1.8405 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5224   -1.1116    2.5208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2635    1.1760    2.8891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1305    0.3004    1.0508 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0953   -0.5022   -0.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2884   -0.6658   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4141   -0.4012    0.1477 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5308    0.1570   -0.4827 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6294   -0.2106    0.2768 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9003    0.2873   -0.3734 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8203    1.8181   -0.3517 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9762   -0.1024   -1.8284 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3829    0.0659   -2.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2700   -0.8568   -1.5054 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0795   -0.1555   -1.5911 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.8159   -1.0290   -0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0872   -0.9531    0.7780 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2941   -2.4496    0.1449 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9760   -0.0690    0.3778 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5856    0.3252    1.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2521    0.1467    2.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283    0.4434    1.3424 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1446    1.9147    1.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9327   -0.0046    1.9005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    1.9280    0.7309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4999    1.8121   -0.6234 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6181    2.1665   -1.6456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6977    0.8555   -0.8107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3902    1.6311    0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5585   -1.7640   -1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5845   -3.1413   -1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9867   -1.2757    0.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7970   -1.6455    1.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8455   -3.2199   -0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6696    0.5487    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3854    0.2219   -1.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2631    1.7631   -0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2238    0.5341    0.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3821   -1.0318    0.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4418    0.3868   -2.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1814   -1.2349   -2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7572   -0.2601   -2.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4545    0.2802    1.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5337   -1.2051    2.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3916   -1.8884    1.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8044   -1.1985    3.3495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042    2.0640    2.5062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0367    1.3725    0.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131   -0.0407   -1.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5106   -1.5314   -0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3830   -1.6881   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4346    0.0231   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7593   -1.4099    0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6060   -1.3388    0.3036 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2423    2.2359   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7658    2.1564   -0.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3211    2.2432    0.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5564   -1.1039   -2.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3343    0.6172   -2.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7150    1.0930   -2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5075   -0.1054   -3.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2923   -1.8658   -1.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8891   -1.5009    1.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8885   -1.5144    0.2536 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3933    0.0981    0.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1202   -3.1794   -0.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4243   -2.6949   -0.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0330   -2.6005    1.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9081    1.3852    1.7152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3352   -0.2368    2.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2004    0.8853    3.1853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0863   -0.8758    2.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1334    2.3276    1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9550    2.2147    0.0684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    2.3736    1.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5684    2.4686    1.3924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355    2.5480    0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3753    2.4796   -0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8851    1.7764   -2.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7423    2.4194    0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7995    1.0434    0.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2025    2.1611   -0.4473 H   0  0  0  0  0  0  0  0  0  0  0  0
 40 39  1  0
 39  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  1
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 36  1  0
 36 37  1  0
 37 38  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  1
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  6
 33 35  1  0
 20 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
  5  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
 37  8  1  0
 35 15  1  0
 30 21  1  0
 33 18  1  0
 40 91  1  0
 40 92  1  0
 40 93  1  0
  5 46  1  1
  6 47  1  0
  6 48  1  0
  7 49  1  0
  7 50  1  0
  9 51  1  0
  9 52  1  0
  9 53  1  0
 11 54  1  1
 36 87  1  0
 36 88  1  0
 37 89  1  1
 38 90  1  0
 13 55  1  0
 13 56  1  0
 13 57  1  0
 14 58  1  0
 15 59  1  6
 16 60  1  0
 16 61  1  0
 17 62  1  0
 17 63  1  0
 18 64  1  1
 20 65  1  1
 31 80  1  0
 31 81  1  0
 32 82  1  0
 32 83  1  0
 34 84  1  0
 34 85  1  0
 34 86  1  0
 22 66  1  0
 22 67  1  0
 22 68  1  0
 23 69  1  0
 23 70  1  0
 24 71  1  0
 24 72  1  0
 25 73  1  6
 28 74  1  0
 28 75  1  0
 28 76  1  0
 29 77  1  0
 29 78  1  0
 29 79  1  0
  1 41  1  0
  1 42  1  0
  3 43  1  0
  3 44  1  0
  4 45  1  0
M  END


  Mrv1652309032205052D          

 40 43  0  0  1  0            999 V2000
    7.6431   -3.4848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6431   -4.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9286   -4.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2142   -4.3098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3576   -4.7223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.0720   -4.3098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7865   -4.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7865   -5.5473    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.9660   -5.4610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6070   -5.4610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9426   -6.2147    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7495   -6.3862    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5780   -7.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9211   -5.5793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5565   -6.5578    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1085   -5.9447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9155   -6.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1704   -6.9008    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.9774   -7.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2324   -7.8570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0393   -8.0285    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7303   -8.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0681   -7.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7965   -6.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4962   -7.2539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.2246   -6.8665    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.4674   -8.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2844   -7.9635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7223   -8.8630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7390   -8.4657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6803   -8.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8733   -8.2985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6184   -7.5139    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0664   -8.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8114   -7.3424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3295   -6.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6150   -6.3542    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8613   -6.6898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3576   -5.5473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6431   -5.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  1  0  0  0
 12 14  1  1  0  0  0
 15 12  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 21 30  1  6  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 15 35  1  0  0  0  0
 11 36  1  0  0  0  0
 36 37  1  0  0  0  0
  8 37  1  0  0  0  0
 37 38  1  1  0  0  0
  5 39  1  1  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0167497

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H](CC[C@]1(C)O[C@H](C[C@H]1O)[C@](C)(O)[C@@H]1CC[C@H]2O[C@H](CC[C@]2(C)O1)[C@]1(C)CC[C@@H](Br)C(C)(C)O1)C(=C)CO

> <INCHI_IDENTIFIER>
InChI=1S/C31H53BrO8/c1-19(18-33)20(36-8)11-14-28(4)22(34)17-26(39-28)31(7,35)25-10-9-23-29(5,38-25)16-13-24(37-23)30(6)15-12-21(32)27(2,3)40-30/h20-26,33-35H,1,9-18H2,2-8H3/t20-,21-,22-,23-,24-,25+,26-,28+,29+,30+,31-/m1/s1

> <INCHI_KEY>
GEFRBFJCRDBHAZ-VKHGRQBQSA-N

> <FORMULA>
C31H53BrO8

> <MOLECULAR_WEIGHT>
633.661

> <EXACT_MASS>
632.292382

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
66.55030371500631

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,5R)-5-[(1R)-1-[(2S,4aR,6R,8aS)-6-[(2S,5R)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-octahydropyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3R)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol

> <ALOGPS_LOGP>
3.83

> <JCHEM_LOGP>
3.260314164666667

> <ALOGPS_LOGS>
-5.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.954100091455803

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.038236482753494

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7542923262130143

> <JCHEM_POLAR_SURFACE_AREA>
106.84000000000002

> <JCHEM_REFRACTIVITY>
156.32869999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,5R)-5-[(1R)-1-[(2S,4aR,6R,8aS)-6-[(2S,5R)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2H-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3R)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      14.267  -6.505   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.267  -8.045   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.933  -8.815   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      11.600  -8.045   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      15.601  -8.815   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.934  -8.045   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.268  -8.815   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.268 -10.355   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.737 -10.194   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      19.800 -10.194   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      20.426 -11.601   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.932 -11.921   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.612 -13.427   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      22.253 -10.415   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      23.439 -12.241   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.469 -11.097   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.976 -11.417   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.451 -12.882   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      27.958 -13.202   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      28.434 -14.666   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      29.940 -14.987   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      29.363 -16.414   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      29.994 -13.447   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      31.354 -12.724   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      32.660 -13.541   0.000  0.00  0.00           C+0
HETATM   26 Br   UNK     0      34.019 -12.818   0.000  0.00  0.00          Br+0
HETATM   27  C   UNK     0      32.606 -15.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      34.131 -14.865   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      33.082 -16.544   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      31.246 -15.803   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      27.403 -15.811   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      25.897 -15.491   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      25.421 -14.026   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      24.391 -15.170   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      23.915 -13.706   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      19.282 -12.631   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      17.948 -11.861   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      16.541 -12.488   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      15.601 -10.355   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      14.267 -11.125   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2    6   39                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   37                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   36                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16   35                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   33                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   31                                                  
CONECT   21   20   22   23   30                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   21                                                       
CONECT   31   20   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   18   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   15                                                       
CONECT   36   11   37                                                       
CONECT   37   36    8   38                                                  
CONECT   38   37                                                            
CONECT   39    5   40                                                       
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₅₃BrO₈

Average Mass

633.6610 Da

Monoisotopic Mass

632.29238 Da

IUPAC Name

(2S,3R,5R)-5-[(1R)-1-[(2S,4aR,6R,8aS)-6-[(2S,5R)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-octahydropyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3R)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol

Traditional Name

(2S,3R,5R)-5-[(1R)-1-[(2S,4aR,6R,8aS)-6-[(2S,5R)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2H-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3R)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol

CAS Registry Number

Not Available

SMILES

CO[C@H](CC[C@]1(C)O[C@H](C[C@H]1O)[C@](C)(O)[C@@H]1CC[C@H]2O[C@H](CC[C@]2(C)O1)[C@]1(C)CC[C@@H](Br)C(C)(C)O1)C(=C)CO

InChI Identifier

InChI=1S/C31H53BrO8/c1-19(18-33)20(36-8)11-14-28(4)22(34)17-26(39-28)31(7,35)25-10-9-23-29(5,38-25)16-13-24(37-23)30(6)15-12-21(32)27(2,3)40-30/h20-26,33-35H,1,9-18H2,2-8H3/t20-,21-,22-,23-,24-,25+,26-,28+,29+,30+,31-/m1/s1

InChI Key

GEFRBFJCRDBHAZ-VKHGRQBQSA-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
Aplysia dactylomela	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Oxane
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Alcohol
Primary alcohol
Organic oxygen compound
Organooxygen compound
Organobromide
Organohalogen compound
Alkyl halide
Alkyl bromide
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	3.83	ALOGPS
logP	3.26	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	13.04	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.84 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	156.33 m³·mol⁻¹	ChemAxon
Polarizability	66.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

29214510

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44551050

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Vera B, Rodriguez AD, Aviles E, Ishikawa Y: Aplysqualenols A and B: Squalene-Derived Polyethers with Antitumoral and Antiviral Activity from the Caribbean Sea Slug Aplysia dactylomela. European J Org Chem. 2009 Nov;2009(31):5327-5336. doi: 10.1002/ejoc.200900775. Epub 2009 Sep 16. [PubMed:23459021 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol (NP0167497)

MOL for NP0167497 ((2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol)

3D MOL for NP0167497 ((2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol)

3D SDF for NP0167497 ((2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol)

3D-SDF for NP0167497 ((2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol)

PDB for NP0167497 ((2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol)

3D PDB for NP0167497 ((2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol)

SMILES for NP0167497 ((2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol)

INCHI for NP0167497 ((2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol)

Structure for NP0167497 ((2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol)

3D Structure for NP0167497 ((2s,3r,5r)-5-[(1r)-1-[(2s,4ar,6r,8as)-6-[(2s,5r)-5-bromo-2,6,6-trimethyloxan-2-yl]-8a-methyl-hexahydro-2h-pyrano[3,2-b]pyran-2-yl]-1-hydroxyethyl]-2-[(3r)-5-hydroxy-3-methoxy-4-methylidenepentyl]-2-methyloxolan-3-ol)