NP-MRD: Showing NP-Card for (1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol (NP0201974)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 21:06:10 UTC

Updated at

2022-09-04 21:06:10 UTC

NP-MRD ID

NP0201974

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol

Description

(1S,3S,6R,7S,9R,10S,12R,15R,16R,18S,20R,21S)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]Tetracos-4-ene-9,10-diol belongs to the class of organic compounds known as 12-beta-hydroxysteroids. These are hydroxysteroids carrying a beta-hydroxyl group at the 12-position. (1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol is found in Phlomoides hamosa. Based on a literature review very few articles have been published on (1S,3S,6R,7S,9R,10S,12R,15R,16R,18S,20R,21S)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]Tetracos-4-ene-9,10-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042223062D          

 36 41  0  0  1  0            999 V2000
    1.0518    3.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688    3.0363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2984    2.4038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1462    2.5501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6709    1.8442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5067    1.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0185    1.2913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3237    2.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7173    0.5232    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2319   -0.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0476    0.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3488    0.7697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1645    0.8929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8634    0.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6791    0.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4949    0.3713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0095   -0.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7960    1.1393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6118    1.2626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2814    1.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0058    2.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0261    3.0037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0184    2.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5641    3.1849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4657    1.6610    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9511    2.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1353    2.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8342    1.4145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7969    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984    0.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3378    1.0222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7125    0.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9170    0.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0037    1.5906    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1993    1.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    1.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 12 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  1  0  0  0
  9 30  1  0  0  0  0
 30 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 31 36  1  1  0  0  0
M  END

     RDKit          3D

 84 89  0  0  0  0  0  0  0  0999 V2000
    6.4696    2.8567    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5173    1.8637    1.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3011    1.2543    0.0737 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9986    1.4371   -0.3843 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0604    0.8031    0.4666 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7132    1.0641   -0.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7297   -0.0517    0.1247 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4419   -0.0917    1.5890 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983   -1.3456   -0.2861 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4321   -2.4217   -0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8868   -2.2946   -0.5478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4581   -0.9740   -0.2584 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9202   -0.8204   -0.6076 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2472   -1.2314   -2.0049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6087   -1.7902    0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0659   -1.6246    0.3168 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.5482   -2.4073    1.4165 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6365   -0.2647    0.3832 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.9508    0.0003    1.7397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7923    0.8335   -0.1830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0207    2.0574    0.6865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3746    2.3922    0.6444 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3364    1.1874   -1.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6702    2.1853   -2.2037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3366    0.5552   -0.2212 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5441    1.5349   -1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0849    1.4832   -0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5331    0.0871   -0.7176 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1848   -0.1445   -2.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4459   -1.6458    0.7297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4862   -0.5819    0.6696 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3306   -0.7148    1.9458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7613   -0.6568    1.5323 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7071   -0.2083    0.0906 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9530   -0.4903   -0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5000   -0.9853   -0.4115 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1530    3.6470    0.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4326    2.4598    0.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6758    3.2841    2.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9551    1.7386   -0.6767 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1857    1.3551    1.4469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2715    1.9574    0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7685    1.4072   -1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3725    0.5933    1.9005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2189   -1.0719    2.0093 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514    0.2758    2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9642   -1.2085   -1.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439   -3.4104   -0.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5282   -3.1635   -0.7610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4582   -0.9099    0.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5389   -2.0450   -2.3183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2621   -0.4495   -2.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2463   -1.7079   -2.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1458   -1.7698    1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3868   -2.8169   -0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4937   -2.2105   -0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1769   -3.3324    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6304   -0.2780   -0.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7762   -0.5066    1.9724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8190    1.7125    1.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3627    2.8954    0.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8624    2.1351    1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3958    1.5737   -1.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4713    0.3151   -2.2155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2377    2.5470   -2.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9168    0.6957    0.8272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5077    1.3226   -2.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8651    2.5859   -0.8621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0609    1.8683    0.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5218    2.1802   -1.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3320   -1.1889   -2.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7528    0.5749   -2.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8777    0.0782   -2.4027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0854   -1.8302    1.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9322   -2.6174    0.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1307    0.1709    2.6100 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0592   -1.5976    2.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3759    0.0467    2.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2437   -1.6553    1.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9978   -1.5896   -0.8570 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9635    0.0399   -1.6177 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8366   -0.2620   -0.0211 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6425   -2.0709   -0.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1103   -0.6180   -1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 30  1  0
 31 30  1  1
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  6
 34 36  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 23 24  1  0
 20 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  6
 34  3  1  0
 28 12  1  0
 31  5  1  0
 36 31  1  0
 25 13  1  0
 28  7  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
  3 40  1  6
  5 41  1  1
  6 42  1  0
  6 43  1  0
  8 44  1  0
  8 45  1  0
  8 46  1  0
  9 47  1  6
 30 74  1  0
 30 75  1  0
 32 76  1  0
 32 77  1  0
 33 78  1  0
 33 79  1  0
 35 80  1  0
 35 81  1  0
 35 82  1  0
 36 83  1  0
 36 84  1  0
 10 48  1  0
 11 49  1  0
 12 50  1  1
 14 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  6
 17 57  1  0
 18 58  1  6
 19 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 23 63  1  0
 23 64  1  0
 24 65  1  0
 25 66  1  1
 26 67  1  0
 26 68  1  0
 27 69  1  0
 27 70  1  0
 29 71  1  0
 29 72  1  0
 29 73  1  0
M  END


  Mrv1652309042223062D          

 36 41  0  0  1  0            999 V2000
    1.0518    3.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688    3.0363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2984    2.4038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1462    2.5501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6709    1.8442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5067    1.9468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0185    1.2913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3237    2.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7173    0.5232    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2319   -0.1216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0476    0.0016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3488    0.7697    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1645    0.8929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8634    0.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6791    0.2480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4949    0.3713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0095   -0.2736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7960    1.1393    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6118    1.2626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2814    1.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0058    2.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0261    3.0037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0184    2.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5641    3.1849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4657    1.6610    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9511    2.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1353    2.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8342    1.4145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7969    2.2387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984    0.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3378    1.0222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7125    0.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9170    0.7318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0037    1.5906    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1993    1.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7062    1.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 20 25  1  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 12 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  1  0  0  0
  9 30  1  0  0  0  0
 30 31  1  0  0  0  0
  5 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 31 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0201974

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1O[C@H]2C[C@]3(C)[C@@H](C[C@]22CC[C@@]1(C)C2)C=C[C@@H]1[C@@]2(C)C[C@@H](O)[C@@H](O)C(CO)(CO)[C@@H]2CC[C@@]31C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O6/c1-25-10-11-29(15-25)12-18-6-7-20-26(2)13-19(33)23(34)30(16-31,17-32)21(26)8-9-27(20,3)28(18,4)14-22(29)36-24(25)35-5/h6-7,18-24,31-34H,8-17H2,1-5H3/t18-,19-,20-,21-,22+,23-,24-,25+,26-,27-,28-,29+/m1/s1

> <INCHI_KEY>
FDDBJIJIYCDAKQ-XNNMAGMHSA-N

> <FORMULA>
C30H48O6

> <MOLECULAR_WEIGHT>
504.708

> <EXACT_MASS>
504.345089266

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
84

> <JCHEM_AVERAGE_POLARIZABILITY>
58.36866060616808

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3S,6R,7S,9R,10S,12R,15R,16R,18S,20R,21S)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0^{1,18}.0^{3,16}.0^{6,15}.0^{7,12}]tetracos-4-ene-9,10-diol

> <JCHEM_LOGP>
2.4523575529999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.596131952148156

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.476849909651474

> <JCHEM_PKA_STRONGEST_BASIC>
-2.821945363810209

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
138.09740000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,6R,7S,9R,10S,12R,15R,16R,18S,20R,21S)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0^{1,18}.0^{3,16}.0^{6,15}.0^{7,12}]tetracos-4-ene-9,10-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.963   7.114   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.435   5.668   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.424   4.487   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.006   4.760   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.986   3.442   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.546   3.634   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.501   2.410   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.071   3.841   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.939   0.977   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.900  -0.227   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.422   0.003   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.984   1.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.507   1.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.945   0.233   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.468   0.463   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.990   0.693   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      14.951  -0.511   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      14.553   2.127   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.075   2.357   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      13.592   3.330   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.944   4.067   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      14.982   5.607   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      13.101   4.790   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      14.120   5.945   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.069   3.100   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.109   4.304   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.586   4.074   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.024   2.640   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.954   4.179   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.410   0.731   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.364   1.908   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.197   0.711   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.712   1.366   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.874   2.969   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.372   3.311   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.185   2.530   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   28                                             
CONECT    8    7                                                            
CONECT    9    7   10   30                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   28                                                  
CONECT   13   12   14   15   25                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   23   25                                             
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23                                                            
CONECT   25   20   13   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   12    7   29                                             
CONECT   29   28                                                            
CONECT   30    9   31                                                       
CONECT   31   30    5   32   36                                             
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    3   35   36                                             
CONECT   35   34                                                            
CONECT   36   34   31                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₆

Average Mass

504.7080 Da

Monoisotopic Mass

504.34509 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@@H]1O[C@H]2C[C@]3(C)[C@@H](C[C@]22CC[C@@]1(C)C2)C=C[C@@H]1[C@@]2(C)C[C@@H](O)[C@@H](O)C(CO)(CO)[C@@H]2CC[C@@]31C

InChI Identifier

InChI=1S/C30H48O6/c1-25-10-11-29(15-25)12-18-6-7-20-26(2)13-19(33)23(34)30(16-31,17-32)21(26)8-9-27(20,3)28(18,4)14-22(29)36-24(25)35-5/h6-7,18-24,31-34H,8-17H2,1-5H3/t18-,19-,20-,21-,22+,23-,24-,25+,26-,27-,28-,29+/m1/s1

InChI Key

FDDBJIJIYCDAKQ-XNNMAGMHSA-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
Phlomoides hamosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 12-beta-hydroxysteroids. These are hydroxysteroids carrying a beta-hydroxyl group at the 12-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

12-beta-hydroxysteroids

Alternative Parents

Substituents

12-beta-hydroxysteroid
Naphthopyran
Naphthalene
Oxepane
Pyran
Oxane
Cyclic alcohol
Secondary alcohol
Organoheterocyclic compound
Acetal
Oxacycle
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organic oxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source

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

162957886

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol (NP0201974)

MOL for NP0201974 ((1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol)

3D MOL for NP0201974 ((1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol)

3D SDF for NP0201974 ((1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol)

3D-SDF for NP0201974 ((1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol)

PDB for NP0201974 ((1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol)

3D PDB for NP0201974 ((1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol)

SMILES for NP0201974 ((1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol)

INCHI for NP0201974 ((1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol)

Structure for NP0201974 ((1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol)

3D Structure for NP0201974 ((1s,3s,6r,7s,9r,10s,12r,15r,16r,18s,20r,21s)-11,11-bis(hydroxymethyl)-20-methoxy-7,15,16,21-tetramethyl-19-oxahexacyclo[19.2.1.0¹,¹⁸.0³,¹⁶.0⁶,¹⁵.0⁷,¹²]tetracos-4-ene-9,10-diol)