NP-MRD: Showing NP-Card for Xestobergsterol B (NP0083232)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-29 04:16:35 UTC

Updated at

2022-04-29 04:16:35 UTC

NP-MRD ID

NP0083232

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xestobergsterol B

Description

(1R,2R,4S,5R,7R,8S,9R,12S,13R,14S,15R,16S,18S,19R,20R)-5,14,15,16,19,20-hexahydroxy-7,9,13-trimethyl-5-(2-methylpropyl)pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosan-3-one belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton. Xestobergsterol B is found in Haliclona sp. Based on a literature review very few articles have been published on (1R,2R,4S,5R,7R,8S,9R,12S,13R,14S,15R,16S,18S,19R,20R)-5,14,15,16,19,20-hexahydroxy-7,9,13-trimethyl-5-(2-methylpropyl)pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosan-3-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206162D          

 34 38  0  0  1  0            999 V2000
    2.6857   -0.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3544    0.2308    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8431    0.8955    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6631    0.8046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9944    0.0491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5057   -0.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8154    0.1307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9914    0.9367    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2793    1.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1977    2.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8124    1.0183    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1437    0.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275   -0.2858    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6091   -1.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8257    1.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5467    2.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5600    3.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2544    1.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5248    1.4342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4029   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118    1.6510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6918    1.7419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2031    1.0772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5345    0.3216    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0458   -0.3431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2258   -0.2522    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1055    0.5034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3832    1.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9255    0.5942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629   -0.9169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3771   -1.0986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8658   -0.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3605    2.4974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    2.3157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  4  9  1  1  0  0  0
  9 10  2  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
 11 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 11 19  1  6  0  0  0
  5 20  1  6  0  0  0
  3 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
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  6  0  0  0
 27 29  1  1  0  0  0
 26 30  1  6  0  0  0
 25 31  1  6  0  0  0
 24 32  1  6  0  0  0
 22 33  1  1  0  0  0
 21 34  1  6  0  0  0
M  END

     RDKit          3D

 78 82  0  0  0  0  0  0  0  0999 V2000
   -6.3657    2.7804   -1.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6946    1.8471   -0.1557 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.6653    0.7953    0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3529    1.4178   -0.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6558    0.5234    0.3186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5397    1.2249    1.5442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2617   -0.8165    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0451   -1.7392    0.8013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4628   -3.1545    0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0682   -1.2338   -0.2397 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2136    0.2457   -0.1628 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2364    0.5783    0.9422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3735    1.5864    1.5974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2104   -0.4879    1.0174 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1988   -0.0722    0.9512 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9060   -0.2732   -0.3629 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5935   -1.5933   -1.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1004   -1.6215   -1.2314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6331   -1.5679    0.0724 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5250   -2.9345    0.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4049   -0.1629   -0.0502 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7995   -1.0979    1.0685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2246   -0.5329   -1.2585 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3923   -1.9231   -1.3218 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5189    0.1698   -1.3873 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4580   -0.7524   -1.9045 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0889    0.7402   -0.1463 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.0014    1.7540   -0.5237 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1091    1.3600    0.7859 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6617    1.2750    0.2780 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7782    1.8637    1.3045 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6966    3.2485    1.0651 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841    1.3399    1.3700 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9603    1.4394    2.7156 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8943    2.1823   -1.9389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5763    3.4377   -1.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0934    3.4231   -0.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5920    2.5258    0.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7167    0.6642    1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6393   -0.1396   -0.3219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7086    1.2141    0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4523    0.9469   -1.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7404    2.3502   -0.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6075    2.1872    1.3325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0229   -0.9396    1.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5834   -1.1824   -0.5219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7151   -1.6041    1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5862   -3.2238    0.5715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2331   -3.3858   -0.5604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0670   -3.8951    1.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3757   -1.6306   -1.2248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0089    0.7817   -1.0875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693   -0.9425    2.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8089   -0.6883    1.6897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6794    0.5282   -1.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0560   -1.5760   -2.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9689   -2.4715   -0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1363   -2.5970   -1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1897   -0.8364   -1.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9383   -2.9048    1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660   -3.1539    0.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9498   -3.7253    0.0954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2022   -2.0312    1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124   -0.5968    2.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8641   -1.4422    0.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6075   -0.2649   -2.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3263   -2.1874   -1.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4827    0.9862   -2.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1315   -1.1406   -2.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7122    0.0131    0.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4956    2.3638   -1.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2806    2.4628    0.9467 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1704    0.9211    1.8140 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6503    1.8434   -0.6755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2641    1.7669    2.2981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4622    3.3939    0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7173    1.9833    0.7639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9643    2.3582    3.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  1
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 33  1  0
 33 34  1  0
 33 31  1  0
 31 32  1  0
 31 30  1  0
 30 29  1  0
 29 27  1  0
 27 28  1  0
 27 25  1  0
 25 26  1  0
 25 23  1  0
 23 24  1  0
 23 21  1  0
 21 22  1  1
 21 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
 11  5  1  0
 19 14  1  0
 19 10  1  0
 16 15  1  0
 21 30  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  2 38  1  1
  3 39  1  0
  3 40  1  0
  3 41  1  0
  4 42  1  0
  4 43  1  0
  6 44  1  0
  7 45  1  0
  7 46  1  0
  8 47  1  1
  9 48  1  0
  9 49  1  0
  9 50  1  0
 10 51  1  6
 11 52  1  6
 14 53  1  1
 15 54  1  1
 33 77  1  6
 34 78  1  0
 31 75  1  1
 32 76  1  0
 30 74  1  6
 29 72  1  0
 29 73  1  0
 27 70  1  1
 28 71  1  0
 25 68  1  6
 26 69  1  0
 23 66  1  6
 24 67  1  0
 22 63  1  0
 22 64  1  0
 22 65  1  0
 16 55  1  6
 17 56  1  0
 17 57  1  0
 18 58  1  0
 18 59  1  0
 20 60  1  0
 20 61  1  0
 20 62  1  0
M  END


  Mrv1652304292206162D          

 34 38  0  0  1  0            999 V2000
    2.6857   -0.5248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3544    0.2308    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8431    0.8955    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6631    0.8046    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9944    0.0491    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5057   -0.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8154    0.1307    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9914    0.9367    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2793    1.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1977    2.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8124    1.0183    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1437    0.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275   -0.2858    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6091   -1.1068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8257    1.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5467    2.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5600    3.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2544    1.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5248    1.4342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4029   -0.6677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5118    1.6510    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6918    1.7419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2031    1.0772    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5345    0.3216    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0458   -0.3431    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2258   -0.2522    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1055    0.5034    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3832    1.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9255    0.5942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629   -0.9169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3771   -1.0986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8658   -0.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3605    2.4974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0005    2.3157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  7  5  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  4  9  1  1  0  0  0
  9 10  2  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
 11 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 11 19  1  6  0  0  0
  5 20  1  6  0  0  0
  3 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
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 28  1  6  0  0  0
 27 29  1  1  0  0  0
 26 30  1  6  0  0  0
 25 31  1  6  0  0  0
 24 32  1  6  0  0  0
 22 33  1  1  0  0  0
 21 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0083232

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C[C@@]1(O)C[C@@H](C)[C@H]2[C@@H]1C(=O)[C@@H]1[C@@H]3[C@@H](O)[C@H](O)[C@H]4C[C@H](O)[C@@H](O)[C@@H](O)[C@]4(C)[C@H]3CC[C@]21C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O7/c1-11(2)9-27(34)10-12(3)17-19(27)23(32)18-16-13(6-7-25(17,18)4)26(5)14(20(29)22(16)31)8-15(28)21(30)24(26)33/h11-22,24,28-31,33-34H,6-10H2,1-5H3/t12-,13+,14-,15+,16-,17+,18+,19-,20-,21-,22-,24-,25-,26-,27-/m1/s1

> <INCHI_KEY>
DGXRPSIAVFYMOL-GXUOCEDMSA-N

> <FORMULA>
C27H44O7

> <MOLECULAR_WEIGHT>
480.642

> <EXACT_MASS>
480.308703757

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.71217704601677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,5R,7R,8S,9R,12S,13R,14S,15R,16S,18S,19R,20R)-5,14,15,16,19,20-hexahydroxy-7,9,13-trimethyl-5-(2-methylpropyl)pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan-3-one

> <ALOGPS_LOGP>
0.65

> <JCHEM_LOGP>
0.6134459176666661

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.585208550785662

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.92896056994772

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0860750311068363

> <JCHEM_POLAR_SURFACE_AREA>
138.45000000000002

> <JCHEM_REFRACTIVITY>
125.52679999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5R,7R,8S,9R,12S,13R,14S,15R,16S,18S,19R,20R)-5,14,15,16,19,20-hexahydroxy-7,9,13-trimethyl-5-(2-methylpropyl)pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       5.013  -0.980   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.395   0.431   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.307   1.672   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.838   1.502   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.456   0.092   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.544  -1.149   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.989   0.244   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.317   1.748   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.988   2.526   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.836   4.058   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.850   1.901   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.468   0.490   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.318  -0.534   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.470  -2.066   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.875   3.441   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.220   4.189   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.245   5.729   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.542   3.398   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.180   2.677   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.219  -1.246   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.689   3.082   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.158   3.252   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.246   2.011   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.864   0.600   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.952  -0.640   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.421  -0.471   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.197   0.940   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.715   2.180   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.728   1.109   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.491  -1.712   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.571  -2.051   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.483  -0.810   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.540   4.662   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       5.601   4.323   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   24                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7   20                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   13                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12   15   19                                             
CONECT   12   11   13                                                       
CONECT   13   12    7   14                                                  
CONECT   14   13                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   11                                                            
CONECT   20    5                                                            
CONECT   21    3   22   34                                                  
CONECT   22   21   23   33                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23    2   25   32                                             
CONECT   25   24   26   31                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27                                                            
CONECT   30   26                                                            
CONECT   31   25                                                            
CONECT   32   24                                                            
CONECT   33   22                                                            
CONECT   34   21                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O₇

Average Mass

480.6420 Da

Monoisotopic Mass

480.30870 Da

IUPAC Name

(1R,2R,4S,5R,7R,8S,9R,12S,13R,14S,15R,16S,18S,19R,20R)-5,14,15,16,19,20-hexahydroxy-7,9,13-trimethyl-5-(2-methylpropyl)pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan-3-one

Traditional Name

(1R,2R,4S,5R,7R,8S,9R,12S,13R,14S,15R,16S,18S,19R,20R)-5,14,15,16,19,20-hexahydroxy-7,9,13-trimethyl-5-(2-methylpropyl)pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosan-3-one

CAS Registry Number

Not Available

SMILES

CC(C)C[C@@]1(O)C[C@@H](C)[C@H]2[C@@H]1C(=O)[C@@H]1[C@@H]3[C@@H](O)[C@H](O)[C@H]4C[C@H](O)[C@@H](O)[C@@H](O)[C@]4(C)[C@H]3CC[C@]21C

InChI Identifier

InChI=1S/C27H44O7/c1-11(2)9-27(34)10-12(3)17-19(27)23(32)18-16-13(6-7-25(17,18)4)26(5)14(20(29)22(16)31)8-15(28)21(30)24(26)33/h11-22,24,28-31,33-34H,6-10H2,1-5H3/t12-,13+,14-,15+,16-,17+,18+,19-,20-,21-,22-,24-,25-,26-,27-/m1/s1

InChI Key

DGXRPSIAVFYMOL-GXUOCEDMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Haliclona sp.	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxosteroids. These are steroid derivatives carrying a C=O group attached to steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Oxosteroids

Direct Parent

Oxosteroids

Alternative Parents

Substituents

23-hydroxysteroid
1-hydroxysteroid
7-hydroxysteroid
3-alpha-hydroxysteroid
Oxosteroid
15-oxosteroid
Hydroxysteroid
6-hydroxysteroid
2-hydroxysteroid
3-hydroxysteroid
Cyclitol or derivatives
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	0.65	ALOGPS
logP	0.61	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.93	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	138.45 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	125.53 m³·mol⁻¹	ChemAxon
Polarizability	53.71 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

24716570

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15167968

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Xestobergsterol B (NP0083232)

MOL for NP0083232 (Xestobergsterol B)

3D MOL for NP0083232 (Xestobergsterol B)

3D SDF for NP0083232 (Xestobergsterol B)

3D-SDF for NP0083232 (Xestobergsterol B)

PDB for NP0083232 (Xestobergsterol B)

3D PDB for NP0083232 (Xestobergsterol B)

SMILES for NP0083232 (Xestobergsterol B)

INCHI for NP0083232 (Xestobergsterol B)

Structure for NP0083232 (Xestobergsterol B)

3D Structure for NP0083232 (Xestobergsterol B)