NP-MRD: Showing NP-Card for (1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol (NP0294155)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 02:33:54 UTC

Updated at

2022-09-10 02:33:54 UTC

NP-MRD ID

NP0294155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol

Description

Campest-22E-en-3beta,4beta,5alpha,6alpha,8beta,14alpha,15alpha,25,28-nonol, also known as campest-22E-en-3β,4β,5α,6α,8β,14α,15α,25,28-nonol, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, campest-22E-en-3beta,4beta,5alpha,6alpha,8beta,14alpha,15alpha,25,28-nonol is considered to be a sterol. (1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol is found in Archaster typicus. Based on a literature review very few articles have been published on campest-22E-en-3beta,4beta,5alpha,6alpha,8beta,14alpha,15alpha,25,28-nonol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309102204332D          

 37 40  0  0  1  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.1509    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3056   -1.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5116   -1.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3962   -3.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5412   -2.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -3.3086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5486   -0.4095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6744   -0.8310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8898   -0.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7019   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   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  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12  2  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 12 36  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END

     RDKit          3D

 85 88  0  0  0  0  0  0  0  0999 V2000
    2.7384   -0.1580    2.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6084   -0.9482    1.7134 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0058   -1.0789    1.2060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4692   -0.6728    0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9139   -0.8723   -0.3470 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0479   -1.8147   -1.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4083   -1.4124   -2.6466 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4948    0.4857   -0.5920 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9544    0.4190   -0.9944 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7332    1.3197   -1.5655 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4763    1.1599    0.6517 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7547   -0.3358    0.6854 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7241   -1.3171   -0.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2880   -1.9154   -0.3882 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0614   -2.5550   -1.5756 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4047   -0.6017   -0.2063 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0027    0.2158   -1.2803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8642   -0.5871   -0.1194 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3189   -1.6723    0.5922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200   -0.7828   -1.5423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9379   -0.7591   -1.5132 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3258   -0.6489   -2.8729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4426    0.5020   -0.8542 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9703    1.5466   -1.6859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9286    0.5494   -0.8658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5318   -0.4151   -0.1009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4001    1.9353   -0.4933 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4669    1.7893    0.4121 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3403    2.7506    0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4539    1.9495    1.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8524    0.7274    0.5380 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3075   -0.4530    1.4087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3683    0.7538    0.3291 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5761    1.4117    1.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    1.3656    1.0452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3398   -0.0787    1.0234 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0793   -0.7151    2.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8004   -0.0748    3.3135 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2553   -0.7149    3.8274 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3582    0.8545    2.9584 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2734   -1.9727    1.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7769   -1.5640    1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8420   -0.1649   -0.6677 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4622   -1.3176    0.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1296   -1.8988   -1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7212   -2.8187   -1.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0172   -1.2094   -3.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4932   -0.3452   -0.4294 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0313    0.3031   -2.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4025    1.4036   -0.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4421    1.7580   -2.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9255    0.8059   -2.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2551    2.2151   -1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6441    0.8811    1.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2408    0.5997    0.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8304   -0.8340   -1.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4014   -2.1495   -0.4067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2112   -2.6014    0.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2859   -3.4719   -1.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0105   -0.3113   -2.1178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2963   -2.4741    0.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0100   -0.0456   -2.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1245   -1.7986   -1.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3866   -1.6836   -1.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1847   -1.1132   -3.0291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5112    1.5225   -2.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2514    0.3849   -1.9212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4496   -0.5708   -0.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7927    2.4980   -1.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2084    1.2748    0.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7527    3.3979   -0.5183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8802    3.4940    0.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7595    2.6964    1.5385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1423    1.7208    1.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5920   -0.6376    2.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5984   -1.3279    0.8356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2572   -0.1502    1.9493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271    1.4226   -0.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7750    1.0877    2.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7617    2.5277    1.3703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4219    1.9937    1.7635 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0067    1.7923    0.0276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1720   -0.8866    2.4071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1263    0.0481    3.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4139   -1.6320    2.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  6
 16 36  1  0
 36 37  1  1
 36 35  1  0
 35 34  1  0
 34 33  1  0
 33 31  1  0
 31 32  1  1
 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  6
 23 21  1  0
 21 22  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  1
 36 12  1  0
 18 33  1  0
 18 16  1  0
 23 31  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  2 41  1  1
  3 42  1  0
  4 43  1  0
  5 44  1  1
  6 45  1  0
  6 46  1  0
  7 47  1  0
  9 48  1  0
  9 49  1  0
  9 50  1  0
 10 51  1  0
 10 52  1  0
 10 53  1  0
 11 54  1  0
 12 55  1  6
 13 56  1  0
 13 57  1  0
 14 58  1  1
 15 59  1  0
 17 60  1  0
 37 83  1  0
 37 84  1  0
 37 85  1  0
 35 81  1  0
 35 82  1  0
 34 79  1  0
 34 80  1  0
 33 78  1  6
 32 75  1  0
 32 76  1  0
 32 77  1  0
 30 73  1  0
 30 74  1  0
 29 71  1  0
 29 72  1  0
 27 69  1  6
 28 70  1  0
 25 67  1  6
 26 68  1  0
 24 66  1  0
 21 64  1  1
 22 65  1  0
 20 62  1  0
 20 63  1  0
 19 61  1  0
M  END

  Mrv1652309102204332D          

 37 40  0  0  1  0            999 V2000
    2.8728   -3.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4338   -2.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -2.1509    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3056   -1.3868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5116   -1.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102   -2.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3962   -3.4536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5412   -2.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615   -3.3086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5486   -0.4095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3708   -0.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6744   -0.8310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8898   -0.5288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7019   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   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  2  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 12  2  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 12 36  1  0  0  0  0
 16 36  1  0  0  0  0
 36 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0294155

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C28H48O9/c1-15(6-7-16(14-29)23(2,3)34)17-12-20(31)28(37)24(17,4)11-9-19-25(5)10-8-18(30)22(33)27(25,36)21(32)13-26(19,28)35/h6-7,15-22,29-37H,8-14H2,1-5H3/b7-6+/t15-,16+,17-,18+,19-,20+,21+,22+,24-,25-,26+,27-,28+/m1/s1

> <INCHI_KEY>
HLYVWVNIGBGPKS-ALUWKOBPSA-N

> <FORMULA>
C28H48O9

> <MOLECULAR_WEIGHT>
528.683

> <EXACT_MASS>
528.329833126

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
58.28161937173692

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,6S,7R,8S,10S,11R,12S,14R,15R)-14-[(2R,3E,5S)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,6,7,8,10,11,12-heptol

> <JCHEM_LOGP>
-1.5744449049999991

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.672106783892907

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.102832715867349

> <JCHEM_PKA_STRONGEST_BASIC>
-2.826101237397319

> <JCHEM_POLAR_SURFACE_AREA>
182.07

> <JCHEM_REFRACTIVITY>
137.1069

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,6S,7R,8S,10S,11R,12S,14R,15R)-14-[(2R,3E,5S)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,6,7,8,10,11,12-heptol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.571  -2.589   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.955  -2.378   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.206  -5.231   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.740  -6.447   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.010  -4.286   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.421  -6.176   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.624  -0.764   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.725  -1.551   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      12.861  -0.987   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.377  -0.716   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    2   13   36                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   36                                             
CONECT   17   16                                                            
CONECT   18   16   19   20   33                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   31                                             
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   23   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   18   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   12   16   37                                             
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
Campest-22E-en-3b,4b,5a,6a,8b,14a,15a,25,28-nonol	Generator
Campest-22E-en-3β,4β,5α,6α,8β,14α,15α,25,28-nonol	Generator

Chemical Formula

C₂₈H₄₈O₉

Average Mass

528.6830 Da

Monoisotopic Mass

528.32983 Da

IUPAC Name

(1R,2R,5S,6S,7R,8S,10S,11R,12S,14R,15R)-14-[(2R,3E,5S)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,6,7,8,10,11,12-heptol

Traditional Name

(1R,2R,5S,6S,7R,8S,10S,11R,12S,14R,15R)-14-[(2R,3E,5S)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane-5,6,7,8,10,11,12-heptol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H48O9/c1-15(6-7-16(14-29)23(2,3)34)17-12-20(31)28(37)24(17,4)11-9-19-25(5)10-8-18(30)22(33)27(25,36)21(32)13-26(19,28)35/h6-7,15-22,29-37H,8-14H2,1-5H3/b7-6+/t15-,16+,17-,18+,19-,20+,21+,22+,24-,25-,26+,27-,28+/m1/s1

InChI Key

HLYVWVNIGBGPKS-ALUWKOBPSA-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
Archaster typicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Ergostane steroids

Direct Parent

Ergosterols and derivatives

Alternative Parents

Substituents

Ergosterol-skeleton
25-hydroxysteroid
3-hydroxysteroid
4-hydroxysteroid
3-beta-hydroxysteroid
14-hydroxysteroid
6-hydroxysteroid
15-hydroxysteroid
5-hydroxysteroid
Hydroxysteroid
Fatty alcohol
Fatty acyl
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Primary alcohol
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Ergosterols and C24-methyl derivatives (LMST01031079 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-1.6	ChemAxon
pKa (Strongest Acidic)	12.1	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	182.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.11 m³·mol⁻¹	ChemAxon
Polarizability	58.28 Å³	ChemAxon
Number of Rings	4	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

29216605

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14354217

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol (NP0294155)

MOL for NP0294155 ((1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol)

3D MOL for NP0294155 ((1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol)

3D SDF for NP0294155 ((1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol)

3D-SDF for NP0294155 ((1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol)

PDB for NP0294155 ((1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol)

3D PDB for NP0294155 ((1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol)

SMILES for NP0294155 ((1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol)

INCHI for NP0294155 ((1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol)

Structure for NP0294155 ((1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol)

3D Structure for NP0294155 ((1r,3s,3ar,3bs,5s,5ar,6s,7s,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5-(hydroxymethyl)-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydrocyclopenta[a]phenanthrene-3,3a,3b,5,5a,6,7-heptol)