NP-MRD: Showing NP-Card for (1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,3e,5r)-5-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol (NP0208835)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 06:00:14 UTC

Updated at

2022-09-05 06:00:14 UTC

NP-MRD ID

NP0208835

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(24R)-5alpha-Cholesta-22-ene-3beta,4beta,6alpha,8beta,15beta,24-hexol, also known as (24R)-5α-cholesta-22-ene-3β,4β,6α,8β,15β,24-hexol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. (1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,3e,5r)-5-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol is found in Aster tataricus and Asteropsis carinifera. Based on a literature review very few articles have been published on (24R)-5alpha-Cholesta-22-ene-3beta,4beta,6alpha,8beta,15beta,24-hexol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052208002D          

 33 36  0  0  1  0            999 V2000
   -0.5116   -1.2739    0.0000 C   0  0  0  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
    0.8120   -0.7354    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
    0.1102   -2.8023    0.0000 O   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
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   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  1  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
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4534   -0.9645    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
    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  8  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 18  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 14 32  1  0  0  0  0
 10 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END

     RDKit          3D

 79 82  0  0  0  0  0  0  0  0999 V2000
    7.6999   -1.1319    0.2338 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5920    0.3094    0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4452    0.4104    2.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4383    1.0049   -0.0581 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5737    0.9587   -1.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1828    0.2796    0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2510    0.0034   -0.5159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0120   -0.7115   -0.1023 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0943   -1.1055    1.3257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8255    0.1792   -0.3598 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7689    0.5106   -1.8675 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3060    0.4947   -2.2498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0775   -0.7115   -2.8258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3649    0.6345   -0.9302 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8092    0.4041   -0.8894 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2609   -0.5126   -1.8359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4813    1.7261   -1.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9841    1.4344   -1.4035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5926    2.6497   -1.7123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5186    0.9775   -0.0867 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9977    0.7729   -0.1889 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2850    0.0031   -1.3152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5842    0.1486    1.0490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2162   -1.0746    0.7824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6340    0.0806    2.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2742   -0.3948    1.9049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7865   -0.2077    0.5020 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0029   -1.4822   -0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3157    0.1510    0.4928 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4546   -0.7854    1.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0577   -0.1654    1.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4835   -0.3391   -0.0880 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2988   -1.7536   -0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4035   -1.2917   -0.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7060   -1.5243   -0.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9782   -1.7471    1.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5197    0.8482    0.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4869    0.3453    2.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9054   -0.4543    2.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9648    1.3554    2.4255 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3590    2.0340    0.3261 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4736    0.0337   -1.7458 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1559    0.0531    1.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4011    0.3064   -1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9149   -1.6717   -0.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3445   -1.9078    1.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1171   -1.5226    1.5948 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9190   -0.2744    2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9647    1.1864    0.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3269   -0.2883   -2.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2120    1.4903   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0615    1.3092   -2.9646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2865   -0.6164   -3.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0824    1.6506   -0.5262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3969   -0.1187   -2.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1508    2.0085   -2.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3014    2.4669   -0.5451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2034    0.7295   -2.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4659    3.2331   -0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3634    1.8180    0.6460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4388    1.7891   -0.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3292    0.5441   -2.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4282    0.8295    1.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0460   -1.3525   -0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0918   -0.5849    2.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6118    1.0969    2.6895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5592    0.1764    2.5682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1244   -1.4682    2.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3756   -1.3401   -1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0601   -2.1054   -0.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7493   -2.1601    0.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2593    1.1449    1.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7875   -0.7993    2.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4417   -1.8107    0.9283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2089    0.9368    1.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5504   -0.6144    2.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0290   -2.0935   -1.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3981   -2.4187    0.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -1.9792   -0.9650 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 32  1  0
 32 33  1  6
 32 31  1  0
 31 30  1  0
 30 29  1  0
 29 27  1  0
 27 28  1  6
 27 26  1  0
 26 25  1  0
 25 23  1  0
 23 24  1  0
 23 21  1  0
 21 22  1  0
 21 20  1  0
 20 18  1  0
 18 19  1  0
 18 17  1  0
 17 15  1  0
 15 16  1  6
 32 10  1  0
 15 29  1  0
 15 14  1  0
 20 27  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
  4 41  1  1
  5 42  1  0
  6 43  1  0
  7 44  1  0
  8 45  1  6
  9 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  1
 11 50  1  0
 11 51  1  0
 12 52  1  6
 13 53  1  0
 14 54  1  1
 33 77  1  0
 33 78  1  0
 33 79  1  0
 31 75  1  0
 31 76  1  0
 30 73  1  0
 30 74  1  0
 29 72  1  1
 28 69  1  0
 28 70  1  0
 28 71  1  0
 26 67  1  0
 26 68  1  0
 25 65  1  0
 25 66  1  0
 23 63  1  1
 24 64  1  0
 21 61  1  6
 22 62  1  0
 20 60  1  1
 18 58  1  6
 19 59  1  0
 17 56  1  0
 17 57  1  0
 16 55  1  0
M  END


  Mrv1652309052208002D          

 33 36  0  0  1  0            999 V2000
   -0.5116   -1.2739    0.0000 C   0  0  0  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
    0.8120   -0.7354    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
    0.1102   -2.8023    0.0000 O   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
    1.7447   -3.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8728   -3.9050    0.0000 C   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  1  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
    4.9853   -1.5952    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4534   -0.9645    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
    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
 10  8  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 18  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 14 32  1  0  0  0  0
 10 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0208835

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C27H46O6/c1-14(2)17(28)7-6-15(3)16-12-19(30)24-25(16,4)11-9-21-26(5)10-8-18(29)23(32)22(26)20(31)13-27(21,24)33/h6-7,14-24,28-33H,8-13H2,1-5H3/b7-6+/t15-,16-,17+,18+,19-,20+,21-,22+,23+,24-,25-,26-,27+/m1/s1

> <INCHI_KEY>
PWLXQPZULYSLCI-UEOSXYPKSA-N

> <FORMULA>
C27H46O6

> <MOLECULAR_WEIGHT>
466.659

> <EXACT_MASS>
466.329439201

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
54.432700533149216

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
1.0843222703333324

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.11231930009884

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.519185844648131

> <JCHEM_PKA_STRONGEST_BASIC>
-1.486736088230534

> <JCHEM_POLAR_SURFACE_AREA>
121.38000000000001

> <JCHEM_REFRACTIVITY>
128.23200000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.955  -2.378   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.571  -2.589   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.516  -1.373   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.151  -4.015   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.206  -5.231   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.676  -4.226   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.624  -0.764   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.313  -1.800   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.377  -0.716   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   32                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   32                                                  
CONECT   15   14   16   17   29                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   27                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   20   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   15   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   14   10   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
(24R)-5a-Cholesta-22-ene-3b,4b,6a,8b,15b,24-hexol	Generator
(24R)-5Α-cholesta-22-ene-3β,4β,6α,8β,15β,24-hexol	Generator

Chemical Formula

C₂₇H₄₆O₆

Average Mass

466.6590 Da

Monoisotopic Mass

466.32944 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C27H46O6/c1-14(2)17(28)7-6-15(3)16-12-19(30)24-25(16,4)11-9-21-26(5)10-8-18(29)23(32)22(26)20(31)13-27(21,24)33/h6-7,14-24,28-33H,8-13H2,1-5H3/b7-6+/t15-,16-,17+,18+,19-,20+,21-,22+,23+,24-,25-,26-,27+/m1/s1

InChI Key

PWLXQPZULYSLCI-UEOSXYPKSA-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
Aster tataricus	LOTUS Database	35616633
Asteropsis carinifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols and derivatives

Alternative Parents

Substituents

Cholesterol-skeleton
24-hydroxysteroid
3-hydroxysteroid
3-beta-hydroxysteroid
4-hydroxysteroid
6-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Polyol
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	1.08	ChemAxon
pKa (Strongest Acidic)	13.52	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	121.38 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	128.23 m³·mol⁻¹	ChemAxon
Polarizability	54.43 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	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

10258019

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21629555

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,3e,5r)-5-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol (NP0208835)

MOL for NP0208835 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,3e,5r)-5-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D MOL for NP0208835 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,3e,5r)-5-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D SDF for NP0208835 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,3e,5r)-5-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D-SDF for NP0208835 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,3e,5r)-5-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

PDB for NP0208835 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,3e,5r)-5-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D PDB for NP0208835 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,3e,5r)-5-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

SMILES for NP0208835 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,3e,5r)-5-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

INCHI for NP0208835 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,3e,5r)-5-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

Structure for NP0208835 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,3e,5r)-5-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)

3D Structure for NP0208835 ((1r,3r,3as,3bs,5s,5as,6r,7s,9as,9br,11ar)-1-[(2r,3e,5r)-5-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-3,3b,5,6,7-pentol)