NP-MRD: Showing NP-Card for Guanacastepene (NP0003289)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2020-12-09 00:32:45 UTC

Updated at

2021-07-15 16:46:02 UTC

NP-MRD ID

NP0003289

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Guanacastepene

Provided By

NPAtlas

Description

(1R,2R,6S,8aR,10aR)-5-formyl-6-hydroxy-8a,10a-dimethyl-3-oxo-1-(propan-2-yl)-1H,2H,3H,6H,7H,8H,8aH,9H,10H,10aH-cyclohexa[f]azulen-2-yl acetate belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom). Guanacastepene is found in Unknown-fungus sp. CR115. It was first documented in 2000 (PMID: 10819296). Based on a literature review very few articles have been published on (1R,2R,6S,8aR,10aR)-5-formyl-6-hydroxy-8a,10a-dimethyl-3-oxo-1-(propan-2-yl)-1H,2H,3H,6H,7H,8H,8aH,9H,10H,10aH-cyclohexa[f]azulen-2-yl acetate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117463D          

 57 59  0  0  0  0            999 V2000
   -5.4557    3.2735    0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1135    2.8288    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5284    3.4432   -0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311    1.7578    0.6347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    1.3852    0.1863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1016    1.5150    1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0884    2.1639    2.2201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0090    0.7177    0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    0.9254    0.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4585    0.2073    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949    0.1979    1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173    0.8439    2.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1751    0.8252    3.3899 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7271   -0.4537    1.0639 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8225   -1.6098    1.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0132   -0.7086   -0.3950 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8322   -1.2736   -1.1091 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6061   -0.4406   -0.9560 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5802    0.6171   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3801   -1.3566   -1.1315 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1223   -0.5886   -1.3432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6777   -0.4189   -0.0658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5386   -1.6168    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0569    0.0003   -0.3643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1354   -0.9343    0.1296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4702   -0.3651   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9975   -2.2917   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0702    2.4350    0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0034    3.8067   -0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3045    3.9745    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910    2.0930   -0.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954    1.8336    1.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537    1.3458    2.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4872    0.2601    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7775   -1.8221    1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8228   -1.4899   -0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4543    0.1757   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -1.3095   -2.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6305   -2.2946   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115    0.7533   -2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9677    0.2931   -2.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564    1.5735   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -1.9540   -2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978   -2.0507   -0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3223    0.4457   -1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -1.0653   -2.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -2.5818    0.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3283   -1.7122    1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4201   -1.5470    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372    0.0726   -1.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1881   -0.9662    1.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431    0.2766   -1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0477    0.0976    0.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1385   -1.1977   -0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2596   -2.3619   -1.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9659   -2.6377   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8139   -3.0901    0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 24  5  1  0  0  0  0
 22  8  1  0  0  0  0
 18 10  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  5 31  1  6  0  0  0
  9 32  1  0  0  0  0
 12 33  1  0  0  0  0
 14 34  1  1  0  0  0
 15 35  1  0  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
 19 40  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 23 47  1  0  0  0  0
 23 48  1  0  0  0  0
 23 49  1  0  0  0  0
 24 50  1  6  0  0  0
 25 51  1  1  0  0  0
 26 52  1  0  0  0  0
 26 53  1  0  0  0  0
 26 54  1  0  0  0  0
 27 55  1  0  0  0  0
 27 56  1  0  0  0  0
 27 57  1  0  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -5.4557    3.2735    0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1135    2.8288    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5284    3.4432   -0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311    1.7578    0.6347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    1.3852    0.1863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1016    1.5150    1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0884    2.1639    2.2201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0090    0.7177    0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    0.9254    0.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4585    0.2073    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949    0.1979    1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173    0.8439    2.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1751    0.8252    3.3899 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7271   -0.4537    1.0639 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8225   -1.6098    1.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0132   -0.7086   -0.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322   -1.2736   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6061   -0.4406   -0.9560 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5802    0.6171   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3801   -1.3566   -1.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223   -0.5886   -1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777   -0.4189   -0.0658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5386   -1.6168    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0569    0.0003   -0.3643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1354   -0.9343    0.1296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4702   -0.3651   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9975   -2.2917   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0702    2.4350    0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0034    3.8067   -0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3045    3.9745    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910    2.0930   -0.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954    1.8336    1.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537    1.3458    2.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4872    0.2601    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7775   -1.8221    1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8228   -1.4899   -0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4543    0.1757   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -1.3095   -2.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6305   -2.2946   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115    0.7533   -2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9677    0.2931   -2.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564    1.5735   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -1.9540   -2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978   -2.0507   -0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3223    0.4457   -1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -1.0653   -2.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -2.5818    0.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3283   -1.7122    1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4201   -1.5470    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372    0.0726   -1.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1881   -0.9662    1.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431    0.2766   -1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0477    0.0976    0.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1385   -1.1977   -0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2596   -2.3619   -1.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9659   -2.6377   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8139   -3.0901    0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 24  5  1  0
 22  8  1  0
 18 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  6
  9 32  1  0
 12 33  1  0
 14 34  1  1
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  6
 25 51  1  1
 26 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
M  END


  Mrv1652306242117463D          

 57 59  0  0  0  0            999 V2000
   -5.4557    3.2735    0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1135    2.8288    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5284    3.4432   -0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311    1.7578    0.6347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    1.3852    0.1863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1016    1.5150    1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0884    2.1639    2.2201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0090    0.7177    0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    0.9254    0.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4585    0.2073    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949    0.1979    1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173    0.8439    2.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1751    0.8252    3.3899 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7271   -0.4537    1.0639 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8225   -1.6098    1.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0132   -0.7086   -0.3950 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8322   -1.2736   -1.1091 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6061   -0.4406   -0.9560 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5802    0.6171   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3801   -1.3566   -1.1315 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1223   -0.5886   -1.3432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6777   -0.4189   -0.0658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5386   -1.6168    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0569    0.0003   -0.3643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1354   -0.9343    0.1296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4702   -0.3651   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9975   -2.2917   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0702    2.4350    0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0034    3.8067   -0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3045    3.9745    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910    2.0930   -0.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954    1.8336    1.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537    1.3458    2.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4872    0.2601    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7775   -1.8221    1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8228   -1.4899   -0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4543    0.1757   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -1.3095   -2.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6305   -2.2946   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115    0.7533   -2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9677    0.2931   -2.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564    1.5735   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -1.9540   -2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978   -2.0507   -0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3223    0.4457   -1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -1.0653   -2.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -2.5818    0.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3283   -1.7122    1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4201   -1.5470    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372    0.0726   -1.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1881   -0.9662    1.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431    0.2766   -1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0477    0.0976    0.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1385   -1.1977   -0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2596   -2.3619   -1.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9659   -2.6377   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8139   -3.0901    0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 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
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 24  5  1  0  0  0  0
 22  8  1  0  0  0  0
 18 10  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  5 31  1  6  0  0  0
  9 32  1  0  0  0  0
 12 33  1  0  0  0  0
 14 34  1  1  0  0  0
 15 35  1  0  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
 19 40  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 20 43  1  0  0  0  0
 20 44  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 23 47  1  0  0  0  0
 23 48  1  0  0  0  0
 23 49  1  0  0  0  0
 24 50  1  6  0  0  0
 25 51  1  1  0  0  0
 26 52  1  0  0  0  0
 26 53  1  0  0  0  0
 26 54  1  0  0  0  0
 27 55  1  0  0  0  0
 27 56  1  0  0  0  0
 27 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003289

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C(C([H])=O)=C2C([H])=C3C(=O)[C@]([H])(OC(=O)C([H])([H])[H])[C@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O5/c1-12(2)18-20(27-13(3)24)19(26)16-10-15-14(11-23)17(25)6-7-21(15,4)8-9-22(16,18)5/h10-12,17-18,20,25H,6-9H2,1-5H3/t17-,18-,20+,21-,22-/m0/s1

> <INCHI_KEY>
KCPNSIPCHJTGHJ-MYHSIESUSA-N

> <FORMULA>
C22H30O5

> <MOLECULAR_WEIGHT>
374.477

> <EXACT_MASS>
374.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.600887063556485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,6S,8aR,10aR)-5-formyl-6-hydroxy-8a,10a-dimethyl-3-oxo-1-(propan-2-yl)-1H,2H,3H,6H,7H,8H,8aH,9H,10H,10aH-cyclohexa[f]azulen-2-yl acetate

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
2.500209774666666

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.42670567750604

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.397050901149825

> <JCHEM_PKA_STRONGEST_BASIC>
-3.062350366064135

> <JCHEM_POLAR_SURFACE_AREA>
80.67

> <JCHEM_REFRACTIVITY>
102.79759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
guanacastepene A

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
   -5.4557    3.2735    0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1135    2.8288    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5284    3.4432   -0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311    1.7578    0.6347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    1.3852    0.1863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1016    1.5150    1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0884    2.1639    2.2201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0090    0.7177    0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    0.9254    0.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4585    0.2073    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949    0.1979    1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173    0.8439    2.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1751    0.8252    3.3899 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7271   -0.4537    1.0639 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8225   -1.6098    1.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0132   -0.7086   -0.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322   -1.2736   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6061   -0.4406   -0.9560 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5802    0.6171   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3801   -1.3566   -1.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223   -0.5886   -1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777   -0.4189   -0.0658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5386   -1.6168    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0569    0.0003   -0.3643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1354   -0.9343    0.1296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4702   -0.3651   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9975   -2.2917   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0702    2.4350    0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0034    3.8067   -0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3045    3.9745    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910    2.0930   -0.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954    1.8336    1.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537    1.3458    2.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4872    0.2601    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7775   -1.8221    1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8228   -1.4899   -0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4543    0.1757   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -1.3095   -2.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6305   -2.2946   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115    0.7533   -2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9677    0.2931   -2.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564    1.5735   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -1.9540   -2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978   -2.0507   -0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3223    0.4457   -1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -1.0653   -2.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -2.5818    0.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3283   -1.7122    1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4201   -1.5470    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372    0.0726   -1.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1881   -0.9662    1.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431    0.2766   -1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0477    0.0976    0.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1385   -1.1977   -0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2596   -2.3619   -1.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9659   -2.6377   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8139   -3.0901    0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 24  5  1  0
 22  8  1  0
 18 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  6
  9 32  1  0
 12 33  1  0
 14 34  1  1
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  6
 25 51  1  1
 26 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.456   3.273   0.548  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.114   2.829   0.101  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.528   3.443  -0.823  0.00  0.00           O+0
HETATM    4  O   UNK     0      -3.431   1.758   0.635  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.190   1.385   0.186  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.102   1.515   1.170  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.088   2.164   2.220  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.009   0.718   0.665  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.277   0.925   0.813  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.458   0.207   0.357  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.395   0.198   1.254  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.217   0.844   2.545  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.175   0.825   3.390  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.727  -0.454   1.064  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.822  -1.610   1.826  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.013  -0.709  -0.395  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.832  -1.274  -1.109  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.606  -0.441  -0.956  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.580   0.617  -2.077  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.380  -1.357  -1.131  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.122  -0.589  -1.343  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.678  -0.419  -0.066  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.539  -1.617   0.828  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.057   0.000  -0.364  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.135  -0.934   0.130  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.470  -0.365  -0.314  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.998  -2.292  -0.491  0.00  0.00           C+0
HETATM   28  H   UNK     0      -6.070   2.435   0.931  0.00  0.00           H+0
HETATM   29  H   UNK     0      -6.003   3.807  -0.228  0.00  0.00           H+0
HETATM   30  H   UNK     0      -5.305   3.974   1.398  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.891   2.093  -0.651  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.495   1.834   1.408  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.354   1.346   2.882  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.487   0.260   1.440  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.777  -1.822   1.968  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.823  -1.490  -0.421  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.454   0.176  -0.900  0.00  0.00           H+0
HETATM   38  H   UNK     0       4.096  -1.310  -2.206  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.631  -2.295  -0.727  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.611   0.753  -2.417  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.968   0.293  -2.924  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.256   1.573  -1.617  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.617  -1.954  -2.052  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.398  -2.051  -0.297  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.322   0.446  -1.709  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.458  -1.065  -2.156  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.473  -2.582   0.285  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.328  -1.712   1.575  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.420  -1.547   1.412  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.237   0.073  -1.468  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.188  -0.966   1.238  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.343   0.277  -1.231  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.048   0.098   0.485  0.00  0.00           H+0
HETATM   54  H   UNK     0      -5.138  -1.198  -0.696  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.260  -2.362  -1.308  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.966  -2.638  -0.965  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.814  -3.090   0.289  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   24   31                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   22                                                  
CONECT    9    8   10   32                                                  
CONECT   10    9   11   18                                                  
CONECT   11   10   12   14                                                  
CONECT   12   11   13   33                                                  
CONECT   13   12                                                            
CONECT   14   11   15   16   34                                             
CONECT   15   14   35                                                       
CONECT   16   14   17   36   37                                             
CONECT   17   16   18   38   39                                             
CONECT   18   17   19   20   10                                             
CONECT   19   18   40   41   42                                             
CONECT   20   18   21   43   44                                             
CONECT   21   20   22   45   46                                             
CONECT   22   21   23   24    8                                             
CONECT   23   22   47   48   49                                             
CONECT   24   22   25    5   50                                             
CONECT   25   24   26   27   51                                             
CONECT   26   25   52   53   54                                             
CONECT   27   25   55   56   57                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    5                                                            
CONECT   32    9                                                            
CONECT   33   12                                                            
CONECT   34   14                                                            
CONECT   35   15                                                            
CONECT   36   16                                                            
CONECT   37   16                                                            
CONECT   38   17                                                            
CONECT   39   17                                                            
CONECT   40   19                                                            
CONECT   41   19                                                            
CONECT   42   19                                                            
CONECT   43   20                                                            
CONECT   44   20                                                            
CONECT   45   21                                                            
CONECT   46   21                                                            
CONECT   47   23                                                            
CONECT   48   23                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
CONECT   52   26                                                            
CONECT   53   26                                                            
CONECT   54   26                                                            
CONECT   55   27                                                            
CONECT   56   27                                                            
CONECT   57   27                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  118    0
END

RDKit          3D

57 59  0  0  0  0  0  0  0  0999 V2000
   -5.4557    3.2735    0.5477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1135    2.8288    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5284    3.4432   -0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311    1.7578    0.6347 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1899    1.3852    0.1863 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1016    1.5150    1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0884    2.1639    2.2201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0090    0.7177    0.6654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769    0.9254    0.8129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4585    0.2073    0.3574 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3949    0.1979    1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2173    0.8439    2.5449 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1751    0.8252    3.3899 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7271   -0.4537    1.0639 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8225   -1.6098    1.8264 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0132   -0.7086   -0.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322   -1.2736   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6061   -0.4406   -0.9560 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5802    0.6171   -2.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3801   -1.3566   -1.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1223   -0.5886   -1.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777   -0.4189   -0.0658 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5386   -1.6168    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0569    0.0003   -0.3643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1354   -0.9343    0.1296 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4702   -0.3651   -0.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9975   -2.2917   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0702    2.4350    0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0034    3.8067   -0.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3045    3.9745    1.3983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910    2.0930   -0.6505 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954    1.8336    1.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537    1.3458    2.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4872    0.2601    1.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7775   -1.8221    1.9677 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8228   -1.4899   -0.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4543    0.1757   -0.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0958   -1.3095   -2.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6305   -2.2946   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115    0.7533   -2.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9677    0.2931   -2.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564    1.5735   -1.6175 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -1.9540   -2.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978   -2.0507   -0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3223    0.4457   -1.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582   -1.0653   -2.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4727   -2.5818    0.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3283   -1.7122    1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4201   -1.5470    1.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372    0.0726   -1.4684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1881   -0.9662    1.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431    0.2766   -1.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0477    0.0976    0.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1385   -1.1977   -0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2596   -2.3619   -1.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9659   -2.6377   -0.9653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8139   -3.0901    0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 24  5  1  0
 22  8  1  0
 18 10  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  5 31  1  6
  9 32  1  0
 12 33  1  0
 14 34  1  1
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 19 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  6
 25 51  1  1
 26 52  1  0
 26 53  1  0
 26 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(1R,2R,6S,8AR,10ar)-5-formyl-6-hydroxy-8a,10a-dimethyl-3-oxo-1-(propan-2-yl)-1H,2H,3H,6H,7H,8H,8ah,9H,10H,10ah-cyclohexa[F]azulen-2-yl acetic acid	Generator

Chemical Formula

C₂₂H₃₀O₅

Average Mass

374.4770 Da

Monoisotopic Mass

374.20932 Da

IUPAC Name

(1R,2R,6S,8aR,10aR)-5-formyl-6-hydroxy-8a,10a-dimethyl-3-oxo-1-(propan-2-yl)-1H,2H,3H,6H,7H,8H,8aH,9H,10H,10aH-cyclohexa[f]azulen-2-yl acetate

Traditional Name

guanacastepene A

CAS Registry Number

Not Available

SMILES

CC(C)[C@H]1[C@@H](OC(C)=O)C(=O)C2=CC3=C(C=O)[C@@H](O)CC[C@@]3(C)CC[C@]12C

InChI Identifier

InChI=1S/C22H30O5/c1-12(2)18-20(27-13(3)24)19(26)16-10-15-14(11-23)17(25)6-7-21(15,4)8-9-22(16,18)5/h10-12,17-18,20,25H,6-9H2,1-5H3/t17-,18-,20+,21-,22-/m0/s1

InChI Key

KCPNSIPCHJTGHJ-MYHSIESUSA-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
Unknown-fungus sp. CR115	NPAtlas	10819296

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha-acyloxy ketones. These are ketones that have an acyloxy substituent alpha to the carbonyl group. They have the general structure R4C(=O)OC(R2)(R3)C(R1)=O (R1=organyl, R4=H or organyl; R2,R3 = any atom).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alpha-acyloxy ketones

Alternative Parents

Substituents

Alpha-acyloxy ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Aldehyde
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.08	ALOGPS
logP	2.5	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	14.4	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.8 m³·mol⁻¹	ChemAxon
Polarizability	41.6 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA005593

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8560244

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Singh MP, Janso JE, Luckman SW, Brady SF, Clardy J, Greenstein M, Maiese WM: Biological activity of guanacastepene, a novel diterpenoid antibiotic produced by an unidentified fungus CR115. J Antibiot (Tokyo). 2000 Mar;53(3):256-61. doi: 10.7164/antibiotics.53.256. [PubMed:10819296 ]

Showing NP-Card for Guanacastepene (NP0003289)

MOL for NP0003289 (Guanacastepene)

3D MOL for NP0003289 (Guanacastepene)

3D SDF for NP0003289 (Guanacastepene)

3D-SDF for NP0003289 (Guanacastepene)

PDB for NP0003289 (Guanacastepene)

3D PDB for NP0003289 (Guanacastepene)

SMILES for NP0003289 (Guanacastepene)

INCHI for NP0003289 (Guanacastepene)

Structure for NP0003289 (Guanacastepene)

3D Structure for NP0003289 (Guanacastepene)