NP-MRD: Showing NP-Card for Integristerone B (NP0081835)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-29 02:54:25 UTC

Updated at

2022-04-29 02:54:25 UTC

NP-MRD ID

NP0081835

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Integristerone B

Description

(1S,2S,3S,4R,5R,7S,11S,14S,15R)-3,4,5,7,11-pentahydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-8-one belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group. Integristerone B is found in Rhaponticum carthamoides and Rhaponticum integrifolium. Based on a literature review very few articles have been published on (1S,2S,3S,4R,5R,7S,11S,14S,15R)-3,4,5,7,11-pentahydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-9-en-8-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204542D          

 36 39  0  0  1  0            999 V2000
   -0.3323   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -1.6450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5838   -2.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7889   -3.9728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404   -2.5662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7601   -1.7902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2920   -1.1595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1041   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3844   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8526   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1965   -2.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6359   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3207   -3.3421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959   -2.1305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.3814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7301   -2.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -2.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.7301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3558   -0.2237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5135   -0.0787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2026    0.6855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3307   -0.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8371    0.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6543    0.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4716    0.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7672    1.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5415   -0.4703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6585   -1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1983   -2.9315    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  6  0  0  0
 10 14  1  6  0  0  0
  9 15  1  6  0  0  0
  8 16  1  6  0  0  0
  7 17  1  6  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 20  1  0  0  0  0
 19 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
 22 25  1  6  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
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 25 35  1  1  0  0  0
 18 36  1  1  0  0  0
M  END

     RDKit          3D

 80 83  0  0  0  0  0  0  0  0999 V2000
    7.3712   -0.7724    0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7288   -1.3439   -0.4461 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.2891   -0.6304   -1.6505 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0233   -2.7044   -0.5138 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2198   -1.1255   -0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9347    0.3374   -0.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4692    0.6694   -0.4167 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9276    0.1465   -1.5901 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7082    0.2744    0.7795 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5713    0.6430    2.0263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6425   -1.1159    0.8640 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    0.8248    1.0413 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2536    2.3107    1.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2599    2.5753    1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165    1.1974    1.0300 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8125    0.6064    2.2788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1089    1.0259    0.3415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8070    2.0565   -0.0839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0596    1.8247   -0.7494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9493    2.6991   -0.8998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3068    0.4663   -1.2883 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5160    0.2358   -2.4304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7263    0.3615   -1.7179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7119    0.0811   -0.6299 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.4267   -1.1207   -0.8526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1043    0.1183    0.7287 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.0443   -0.4873    1.6001 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8291   -0.6092    0.9127 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0419   -1.9478    1.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8913   -0.5927   -0.2801 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1021   -1.9197   -0.9815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5150   -0.3971    0.2068 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4612   -1.1990   -0.5206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0767   -0.9081   -0.0148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2436    0.5176    0.1392 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2488    1.2424   -1.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4216   -1.1488    0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4459    0.3367    0.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8962   -1.1396    1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6030    0.3863   -1.3345 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1527   -1.2184   -2.0526 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5085   -0.6246   -2.4335 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3689   -3.1857   -1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8634   -1.5035   -1.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7314   -1.7440    0.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4058    0.7704   -1.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4774    0.8619    0.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4513    1.7912   -0.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3952    0.5236   -2.3615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4928    0.0596    2.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6858    1.7243    2.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9518    0.3064    2.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6748   -1.4578    1.7737 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0733    0.4121    2.0546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966    2.5978    2.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7427    2.9144    0.4480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047    3.0751    2.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4691    3.1702    0.1712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5127    1.0518    2.8157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4819    3.0761    0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9564   -0.4588   -3.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9879    1.3667   -2.1705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8773   -0.3370   -2.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5332    0.8612   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7206   -1.5335   -0.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0623    1.1765    1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9178   -0.1242    2.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3098   -0.1441    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1648   -1.9949    2.3149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9412   -1.9072   -1.7064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3117   -2.7475   -0.2725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2111   -2.2317   -1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4669   -0.7993    1.2671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5034   -1.0678   -1.6209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6441   -2.2749   -0.2620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6354   -1.3801   -0.7234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0863   -1.4209    0.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7230    1.7627   -1.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0063    2.0508   -1.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2748    0.5370   -2.0436 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  6
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  6
  9 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  1
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  6
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  6
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  6
 35 12  1  0
 35 15  1  0
 32 17  1  0
 30 21  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  0
  3 41  1  0
  3 42  1  0
  4 43  1  0
  5 44  1  0
  5 45  1  0
  6 46  1  0
  6 47  1  0
  7 48  1  6
  8 49  1  0
 10 50  1  0
 10 51  1  0
 10 52  1  0
 11 53  1  0
 12 54  1  1
 13 55  1  0
 13 56  1  0
 14 57  1  0
 14 58  1  0
 16 59  1  0
 18 60  1  0
 22 61  1  0
 23 62  1  0
 23 63  1  0
 24 64  1  1
 25 65  1  0
 26 66  1  1
 27 67  1  0
 28 68  1  1
 29 69  1  0
 31 70  1  0
 31 71  1  0
 31 72  1  0
 32 73  1  1
 33 74  1  0
 33 75  1  0
 34 76  1  0
 34 77  1  0
 36 78  1  0
 36 79  1  0
 36 80  1  0
M  END


  Mrv1652304292204542D          

 36 39  0  0  1  0            999 V2000
   -0.3323   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -1.6450    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5838   -2.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035   -3.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7889   -3.9728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404   -2.5662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7601   -1.7902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2920   -1.1595    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1041   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3844   -2.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8526   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1965   -2.2259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6359   -0.6740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4798   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3207   -3.3421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959   -2.1305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5008   -1.3814    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7301   -2.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -2.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.7301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3558   -0.2237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5135   -0.0787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2026    0.6855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3307   -0.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8371    0.4598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6543    0.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4716    0.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7672    1.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5415   -0.4703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6585   -1.2364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1983   -2.9315    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  6  0  0  0
 10 14  1  6  0  0  0
  9 15  1  6  0  0  0
  8 16  1  6  0  0  0
  7 17  1  6  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  1 20  1  0  0  0  0
 19 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 18 24  1  0  0  0  0
 22 25  1  6  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
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 25 35  1  1  0  0  0
 18 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0081835

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)CC[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@]4(O)C[C@@H](O)[C@@H](O)[C@@H](O)[C@]4(C)[C@H]3CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C27H44O9/c1-22(2,33)9-8-18(29)25(5,34)17-7-11-26(35)15-12-19(30)27(36)13-16(28)20(31)21(32)24(27,4)14(15)6-10-23(17,26)3/h12,14,16-18,20-21,28-29,31-36H,6-11,13H2,1-5H3/t14-,16+,17-,18+,20+,21+,23+,24-,25+,26+,27+/m0/s1

> <INCHI_KEY>
NVWOXHIJJRKUQA-RUFJGOCRSA-N

> <FORMULA>
C27H44O9

> <MOLECULAR_WEIGHT>
512.64

> <EXACT_MASS>
512.298532997

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.19764795170779

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3S,4R,5R,7S,11S,14S,15R)-3,4,5,7,11-pentahydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

> <ALOGPS_LOGP>
0.46

> <JCHEM_LOGP>
-1.1293530713333344

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.990430054787861

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.336263731681324

> <JCHEM_PKA_STRONGEST_BASIC>
-3.230233666698555

> <JCHEM_POLAR_SURFACE_AREA>
178.91

> <JCHEM_REFRACTIVITY>
131.4397

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3S,4R,5R,7S,11S,14S,15R)-3,4,5,7,11-pentahydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-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      -0.620  -1.622   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.097  -3.071   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.090  -4.248   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.567  -5.696   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.949  -5.967   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.473  -7.416   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.942  -4.790   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.419  -3.342   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.412  -2.164   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.928  -2.436   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.451  -3.884   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.458  -5.061   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.967  -4.155   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.920  -1.258   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.888  -0.716   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.896  -1.893   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.465  -6.239   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.606  -3.977   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.129  -2.529   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.136  -1.351   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.801  -1.143   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.668  -2.579   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.096  -4.058   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.822  -4.922   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.613  -1.363   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.398  -0.418   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.559  -0.147   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.978   1.280   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -8.084  -0.358   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -9.029   0.858   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -10.555   0.648   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -12.080   0.437   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.765   2.173   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -10.344  -0.878   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -6.829  -2.308   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.237  -5.472   0.000  0.00  0.00           O+0
CONECT    1    2   20                                                       
CONECT    2    1    3    8                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12   17                                             
CONECT    8    7    2    9   16                                             
CONECT    9    8   10   15                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11                                                            
CONECT   14   10                                                            
CONECT   15    9                                                            
CONECT   16    8                                                            
CONECT   17    7                                                            
CONECT   18    3   19   24   36                                             
CONECT   19   18   20   21   22                                             
CONECT   20   19    1                                                       
CONECT   21   19                                                            
CONECT   22   19   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23   18                                                       
CONECT   25   22   26   27   35                                             
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31                                                            
CONECT   35   25                                                            
CONECT   36   18                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₄O₉

Average Mass

512.6400 Da

Monoisotopic Mass

512.29853 Da

IUPAC Name

(1S,2S,3S,4R,5R,7S,11S,14S,15R)-3,4,5,7,11-pentahydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

Traditional Name

(1S,2S,3S,4R,5R,7S,11S,14S,15R)-3,4,5,7,11-pentahydroxy-2,15-dimethyl-14-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-8-one

CAS Registry Number

Not Available

SMILES

CC(C)(O)CC[C@@H](O)[C@](C)(O)[C@H]1CC[C@@]2(O)C3=CC(=O)[C@]4(O)C[C@@H](O)[C@@H](O)[C@@H](O)[C@]4(C)[C@H]3CC[C@]12C

InChI Identifier

InChI=1S/C27H44O9/c1-22(2,33)9-8-18(29)25(5,34)17-7-11-26(35)15-12-19(30)27(36)13-16(28)20(31)21(32)24(27,4)14(15)6-10-23(17,26)3/h12,14,16-18,20-21,28-29,31-36H,6-11,13H2,1-5H3/t14-,16+,17-,18+,20+,21+,23+,24-,25+,26+,27+/m0/s1

InChI Key

NVWOXHIJJRKUQA-RUFJGOCRSA-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
Rhaponticum carthamoides	Plant	KNApSAcK
Rhaponticum integrifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or derivatives bearing at least hydroxyl group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Hydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

Hexahydroxy bile acid, alcohol, or derivatives
Cholesterol-skeleton
Cholesterol
Cholestane-skeleton
25-hydroxysteroid
Hydroxy bile acid, alcohol, or derivatives
22-hydroxysteroid
20-hydroxysteroid
1-hydroxysteroid
6-oxosteroid
3-beta-hydroxysteroid
3-hydroxysteroid
Oxosteroid
3-hydroxy-delta-7-steroid
Hydroxysteroid
5-hydroxysteroid
14-hydroxysteroid
2-hydroxysteroid
Delta-7-steroid
Cyclohexenone
Cyclitol or derivatives
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
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	0.46	ALOGPS
logP	-1.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.34	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	178.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	131.44 m³·mol⁻¹	ChemAxon
Polarizability	55.2 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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

152743375

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Integristerone B (NP0081835)

MOL for NP0081835 (Integristerone B)

3D MOL for NP0081835 (Integristerone B)

3D SDF for NP0081835 (Integristerone B)

3D-SDF for NP0081835 (Integristerone B)

PDB for NP0081835 (Integristerone B)

3D PDB for NP0081835 (Integristerone B)

SMILES for NP0081835 (Integristerone B)

INCHI for NP0081835 (Integristerone B)

Structure for NP0081835 (Integristerone B)

3D Structure for NP0081835 (Integristerone B)