NP-MRD: Showing NP-Card for Andrographolide (NP0026860)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-19 18:38:38 UTC

Updated at

2021-08-20 00:00:10 UTC

NP-MRD ID

NP0026860

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Andrographolide

Provided By

JEOL Database JEOL Logo

Description

Andrographolide is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Andrographolide is found in Eupatorium adenophorum , Cymbopogon schoenanthus, Ginkgo biloba and human urine. Andrographolide was first documented in 2006 (PMID: 15894448). Based on a literature review a small amount of articles have been published on Andrographolide (PMID: 18464090) (PMID: 19110075) (PMID: 22026410) (PMID: 22512591).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120383D          

 55 57  0  0  0  0            999 V2000
    1.3171    0.6407    1.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -0.2073    0.9846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9561   -1.5837    0.5921 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8230   -1.7982   -0.9162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6119   -1.5011   -1.4124 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0719   -0.0335   -1.0236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2128    1.0854   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414    0.1527   -1.4862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7860   -0.2240   -2.9434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3755   -1.6603   -3.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6355   -1.9243   -4.6247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8895   -1.9703   -2.8925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7270   -3.5185   -2.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852   -1.3574   -3.9330 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0604   -1.9453   -5.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    0.0847    0.5636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5885    1.3819    1.1579 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8346    1.2904    2.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0383    1.1628    3.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028    1.0995    4.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424    1.3109    5.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5048    0.8032    4.9615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1647    0.4038    3.7538 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3799    1.0242    2.6158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8957    2.3053    2.2680 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344    0.3478    1.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417    1.6522    1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3611   -2.3333    1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -1.7494    0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5539   -1.1734   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0988   -2.8368   -1.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -2.1573   -0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726    2.0654   -1.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3699    1.1809   -2.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8588    0.9425   -1.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.1945   -1.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028   -0.4541   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8534   -0.1011   -3.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    0.4694   -3.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -2.3319   -2.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5948   -1.8219   -4.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220   -3.8214   -2.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033   -3.9210   -3.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824   -4.0180   -2.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685   -0.2889   -4.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1275   -1.5085   -3.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0279   -1.9943   -5.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735   -0.7375    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533    2.2534    0.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5408    1.6051    0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546    1.3578    3.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2006    0.7549    3.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1553   -0.6912    3.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    0.3901    1.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7787    2.9030    3.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0  0  0  0
  9 10  1  0  0  0  0
  6  7  1  6  0  0  0
  9  8  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 14  1  6  0  0  0
 12  5  1  0  0  0  0
 12 13  1  0  0  0  0
  6  8  1  0  0  0  0
 17 18  1  0  0  0  0
  6 16  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
  2 16  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 19  1  0  0  0  0
  6  5  1  0  0  0  0
 24 25  1  0  0  0  0
  2  1  2  3  0  0  0
 20 21  2  0  0  0  0
 14 15  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
 10 40  1  1  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
  5 32  1  1  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
 16 48  1  1  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 17 49  1  0  0  0  0
 17 50  1  0  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
 11 41  1  0  0  0  0
 14 45  1  0  0  0  0
 14 46  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
 18 51  1  0  0  0  0
 23 52  1  0  0  0  0
 23 53  1  0  0  0  0
 24 54  1  6  0  0  0
 25 55  1  0  0  0  0
 15 47  1  0  0  0  0
M  END

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
    1.3171    0.6407    1.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -0.2073    0.9846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9561   -1.5837    0.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230   -1.7982   -0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6119   -1.5011   -1.4124 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0719   -0.0335   -1.0236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2128    1.0854   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414    0.1527   -1.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860   -0.2240   -2.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3755   -1.6603   -3.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6355   -1.9243   -4.6247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8895   -1.9703   -2.8925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7270   -3.5185   -2.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852   -1.3574   -3.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0604   -1.9453   -5.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    0.0847    0.5636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5885    1.3819    1.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346    1.2904    2.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0383    1.1628    3.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028    1.0995    4.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424    1.3109    5.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5048    0.8032    4.9615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1647    0.4038    3.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3799    1.0242    2.6158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8957    2.3053    2.2680 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344    0.3478    1.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417    1.6522    1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3611   -2.3333    1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -1.7494    0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5539   -1.1734   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0988   -2.8368   -1.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -2.1573   -0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726    2.0654   -1.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3699    1.1809   -2.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8588    0.9425   -1.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.1945   -1.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028   -0.4541   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8534   -0.1011   -3.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    0.4694   -3.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -2.3319   -2.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5948   -1.8219   -4.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220   -3.8214   -2.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033   -3.9210   -3.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824   -4.0180   -2.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685   -0.2889   -4.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1275   -1.5085   -3.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0279   -1.9943   -5.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735   -0.7375    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533    2.2534    0.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5408    1.6051    0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546    1.3578    3.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2006    0.7549    3.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1553   -0.6912    3.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    0.3901    1.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7787    2.9030    3.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
  9 10  1  0
  6  7  1  6
  9  8  1  0
 10 11  1  0
 10 12  1  0
 12 14  1  6
 12  5  1  0
 12 13  1  0
  6  8  1  0
 17 18  1  0
  6 16  1  0
 18 19  2  0
 19 20  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2 16  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 19  1  0
  6  5  1  0
 24 25  1  0
  2  1  2  3
 20 21  2  0
 14 15  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  1
  8 36  1  0
  8 37  1  0
  5 32  1  1
  4 30  1  0
  4 31  1  0
  3 28  1  0
  3 29  1  0
 16 48  1  1
  1 26  1  0
  1 27  1  0
 17 49  1  0
 17 50  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
 11 41  1  0
 14 45  1  0
 14 46  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 18 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  6
 25 55  1  0
 15 47  1  0
M  END


  Mrv1652306192120383D          

 55 57  0  0  0  0            999 V2000
    1.3171    0.6407    1.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -0.2073    0.9846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9561   -1.5837    0.5921 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8230   -1.7982   -0.9162 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6119   -1.5011   -1.4124 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0719   -0.0335   -1.0236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2128    1.0854   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414    0.1527   -1.4862 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7860   -0.2240   -2.9434 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3755   -1.6603   -3.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6355   -1.9243   -4.6247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8895   -1.9703   -2.8925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7270   -3.5185   -2.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852   -1.3574   -3.9330 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0604   -1.9453   -5.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    0.0847    0.5636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5885    1.3819    1.1579 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8346    1.2904    2.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0383    1.1628    3.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028    1.0995    4.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424    1.3109    5.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5048    0.8032    4.9615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1647    0.4038    3.7538 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3799    1.0242    2.6158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8957    2.3053    2.2680 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344    0.3478    1.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417    1.6522    1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3611   -2.3333    1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -1.7494    0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5539   -1.1734   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0988   -2.8368   -1.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -2.1573   -0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726    2.0654   -1.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3699    1.1809   -2.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8588    0.9425   -1.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.1945   -1.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028   -0.4541   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8534   -0.1011   -3.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    0.4694   -3.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -2.3319   -2.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5948   -1.8219   -4.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220   -3.8214   -2.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033   -3.9210   -3.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824   -4.0180   -2.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685   -0.2889   -4.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1275   -1.5085   -3.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0279   -1.9943   -5.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735   -0.7375    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533    2.2534    0.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5408    1.6051    0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546    1.3578    3.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2006    0.7549    3.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1553   -0.6912    3.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    0.3901    1.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7787    2.9030    3.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0  0  0  0
  9 10  1  0  0  0  0
  6  7  1  6  0  0  0
  9  8  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 14  1  6  0  0  0
 12  5  1  0  0  0  0
 12 13  1  0  0  0  0
  6  8  1  0  0  0  0
 17 18  1  0  0  0  0
  6 16  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
  2 16  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 19  1  0  0  0  0
  6  5  1  0  0  0  0
 24 25  1  0  0  0  0
  2  1  2  3  0  0  0
 20 21  2  0  0  0  0
 14 15  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
 10 40  1  1  0  0  0
  8 36  1  0  0  0  0
  8 37  1  0  0  0  0
  5 32  1  1  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
 16 48  1  1  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 17 49  1  0  0  0  0
 17 50  1  0  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
 11 41  1  0  0  0  0
 14 45  1  0  0  0  0
 14 46  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
 18 51  1  0  0  0  0
 23 52  1  0  0  0  0
 23 53  1  0  0  0  0
 24 54  1  6  0  0  0
 25 55  1  0  0  0  0
 15 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0026860

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]1(C([H])([H])[H])[C@]([H])(O[H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@@]([H])(C(=C([H])[H])C([H])([H])C([H])([H])[C@]12[H])C([H])([H])C(\[H])=C1\C(=O)OC([H])([H])[C@@]1([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1

> <INCHI_KEY>
BOJKULTULYSRAS-OTESTREVSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.455

> <EXACT_MASS>
350.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.171310948030055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one

> <ALOGPS_LOGP>
1.57

> <JCHEM_LOGP>
1.6623216726666663

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.523095966386343

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.477875995202613

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7854554977528654

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
94.93049999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
    1.3171    0.6407    1.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -0.2073    0.9846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9561   -1.5837    0.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230   -1.7982   -0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6119   -1.5011   -1.4124 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0719   -0.0335   -1.0236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2128    1.0854   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414    0.1527   -1.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860   -0.2240   -2.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3755   -1.6603   -3.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6355   -1.9243   -4.6247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8895   -1.9703   -2.8925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7270   -3.5185   -2.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852   -1.3574   -3.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0604   -1.9453   -5.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    0.0847    0.5636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5885    1.3819    1.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346    1.2904    2.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0383    1.1628    3.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028    1.0995    4.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424    1.3109    5.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5048    0.8032    4.9615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1647    0.4038    3.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3799    1.0242    2.6158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8957    2.3053    2.2680 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344    0.3478    1.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417    1.6522    1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3611   -2.3333    1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -1.7494    0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5539   -1.1734   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0988   -2.8368   -1.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -2.1573   -0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726    2.0654   -1.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3699    1.1809   -2.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8588    0.9425   -1.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.1945   -1.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028   -0.4541   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8534   -0.1011   -3.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    0.4694   -3.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -2.3319   -2.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5948   -1.8219   -4.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220   -3.8214   -2.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033   -3.9210   -3.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824   -4.0180   -2.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685   -0.2889   -4.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1275   -1.5085   -3.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0279   -1.9943   -5.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735   -0.7375    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533    2.2534    0.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5408    1.6051    0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546    1.3578    3.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2006    0.7549    3.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1553   -0.6912    3.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    0.3901    1.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7787    2.9030    3.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
  9 10  1  0
  6  7  1  6
  9  8  1  0
 10 11  1  0
 10 12  1  0
 12 14  1  6
 12  5  1  0
 12 13  1  0
  6  8  1  0
 17 18  1  0
  6 16  1  0
 18 19  2  0
 19 20  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2 16  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 19  1  0
  6  5  1  0
 24 25  1  0
  2  1  2  3
 20 21  2  0
 14 15  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  1
  8 36  1  0
  8 37  1  0
  5 32  1  1
  4 30  1  0
  4 31  1  0
  3 28  1  0
  3 29  1  0
 16 48  1  1
  1 26  1  0
  1 27  1  0
 17 49  1  0
 17 50  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
 11 41  1  0
 14 45  1  0
 14 46  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 18 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  6
 25 55  1  0
 15 47  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       1.317   0.641   1.605  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.479  -0.207   0.985  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.956  -1.584   0.592  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.823  -1.798  -0.916  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.612  -1.501  -1.412  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.072  -0.034  -1.024  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.213   1.085  -1.664  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.541   0.153  -1.486  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.786  -0.224  -2.943  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.376  -1.660  -3.243  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.636  -1.924  -4.625  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.890  -1.970  -2.893  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.727  -3.519  -2.974  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.085  -1.357  -3.933  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.060  -1.945  -5.225  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.968   0.085   0.564  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.589   1.382   1.158  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.835   1.290   2.646  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.038   1.163   3.226  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.203   1.099   4.696  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.342   1.311   5.529  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.505   0.803   4.962  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.165   0.404   3.754  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.380   1.024   2.616  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.896   2.305   2.268  0.00  0.00           O+0
HETATM   26  H   UNK     0       2.334   0.348   1.853  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.042   1.652   1.881  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.361  -2.333   1.129  0.00  0.00           H+0
HETATM   29  H   UNK     0       2.000  -1.749   0.885  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.554  -1.173  -1.441  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.099  -2.837  -1.123  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.259  -2.157  -0.805  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.473   2.065  -1.249  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.370   1.181  -2.737  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.859   0.943  -1.503  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.858   1.194  -1.362  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.203  -0.454  -0.854  0.00  0.00           H+0
HETATM   38  H   UNK     0      -3.853  -0.101  -3.169  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.278   0.469  -3.623  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.025  -2.332  -2.665  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.595  -1.822  -4.765  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.322  -3.821  -2.896  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.103  -3.921  -3.921  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.282  -4.018  -2.172  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.069  -0.289  -4.069  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.127  -1.508  -3.639  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.028  -1.994  -5.387  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.573  -0.738   0.977  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.953   2.253   0.964  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.541   1.605   0.671  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.955   1.358   3.285  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.201   0.755   3.788  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.155  -0.691   3.714  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.405   0.390   1.725  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.779   2.903   3.029  0.00  0.00           H+0
CONECT    1    2   26   27                                                  
CONECT    2    3   16    1                                                  
CONECT    3    4    2   28   29                                             
CONECT    4    5    3   30   31                                             
CONECT    5   12    4    6   32                                             
CONECT    6    7    8   16    5                                             
CONECT    7    6   33   34   35                                             
CONECT    8    9    6   36   37                                             
CONECT    9   10    8   38   39                                             
CONECT   10    9   11   12   40                                             
CONECT   11   10   41                                                       
CONECT   12   10   14    5   13                                             
CONECT   13   12   42   43   44                                             
CONECT   14   12   15   45   46                                             
CONECT   15   14   47                                                       
CONECT   16   17    6    2   48                                             
CONECT   17   16   18   49   50                                             
CONECT   18   17   19   51                                                  
CONECT   19   18   20   24                                                  
CONECT   20   19   22   21                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   52   53                                             
CONECT   24   23   19   25   54                                             
CONECT   25   24   55                                                       
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    7                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36    8                                                            
CONECT   37    8                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   14                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   17                                                            
CONECT   50   17                                                            
CONECT   51   18                                                            
CONECT   52   23                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
    1.3171    0.6407    1.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -0.2073    0.9846 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9561   -1.5837    0.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8230   -1.7982   -0.9162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6119   -1.5011   -1.4124 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0719   -0.0335   -1.0236 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2128    1.0854   -1.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5414    0.1527   -1.4862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7860   -0.2240   -2.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3755   -1.6603   -3.2426 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6355   -1.9243   -4.6247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8895   -1.9703   -2.8925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7270   -3.5185   -2.9741 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0852   -1.3574   -3.9330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0604   -1.9453   -5.2248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9676    0.0847    0.5636 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5885    1.3819    1.1579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346    1.2904    2.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0383    1.1628    3.2263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028    1.0995    4.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424    1.3109    5.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5048    0.8032    4.9615 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1647    0.4038    3.7538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3799    1.0242    2.6158 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8957    2.3053    2.2680 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344    0.3478    1.8526 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0417    1.6522    1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3611   -2.3333    1.1287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000   -1.7494    0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5539   -1.1734   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0988   -2.8368   -1.1232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2590   -2.1573   -0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4726    2.0654   -1.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3699    1.1809   -2.7374 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8588    0.9425   -1.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.1945   -1.3618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2028   -0.4541   -0.8538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8534   -0.1011   -3.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781    0.4694   -3.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0246   -2.3319   -2.6649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5948   -1.8219   -4.7646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3220   -3.8214   -2.8959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1033   -3.9210   -3.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2824   -4.0180   -2.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685   -0.2889   -4.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1275   -1.5085   -3.6391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0279   -1.9943   -5.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5735   -0.7375    0.9772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9533    2.2534    0.9638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5408    1.6051    0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9546    1.3578    3.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2006    0.7549    3.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1553   -0.6912    3.7138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4054    0.3901    1.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7787    2.9030    3.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
  9 10  1  0
  6  7  1  6
  9  8  1  0
 10 11  1  0
 10 12  1  0
 12 14  1  6
 12  5  1  0
 12 13  1  0
  6  8  1  0
 17 18  1  0
  6 16  1  0
 18 19  2  0
 19 20  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2 16  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 19  1  0
  6  5  1  0
 24 25  1  0
  2  1  2  3
 20 21  2  0
 14 15  1  0
  9 38  1  0
  9 39  1  0
 10 40  1  1
  8 36  1  0
  8 37  1  0
  5 32  1  1
  4 30  1  0
  4 31  1  0
  3 28  1  0
  3 29  1  0
 16 48  1  1
  1 26  1  0
  1 27  1  0
 17 49  1  0
 17 50  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
 11 41  1  0
 14 45  1  0
 14 46  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 18 51  1  0
 23 52  1  0
 23 53  1  0
 24 54  1  6
 25 55  1  0
 15 47  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1R-(1-alpha(e(S)),4Abeta,5alpha,6alpha,8aalpha))-3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-2(3H)-furanone	ChEBI
3-(2-(Decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl)ethylidene)dihydro-4-hydroxyfuran-2(3H)-one	ChEBI
3alpha,14,15,18-Tetrahydroxy-5b,9BH,10a-labda-8(20),12-dien-16-Oic acid gamma-lactone	ChEBI
(1R-(1-a(e(S)),4Abeta,5a,6a,8aalpha))-3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-2(3H)-furanone	Generator
(1R-(1-Α(e(S)),4abeta,5α,6α,8aalpha))-3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-2(3H)-furanone	Generator
3a,14,15,18-Tetrahydroxy-5b,9BH,10a-labda-8(20),12-dien-16-Oate g-lactone	Generator
3a,14,15,18-Tetrahydroxy-5b,9BH,10a-labda-8(20),12-dien-16-Oic acid g-lactone	Generator
3alpha,14,15,18-Tetrahydroxy-5b,9BH,10a-labda-8(20),12-dien-16-Oate gamma-lactone	Generator
3Α,14,15,18-tetrahydroxy-5b,9BH,10a-labda-8(20),12-dien-16-Oate γ-lactone	Generator
3Α,14,15,18-tetrahydroxy-5b,9BH,10a-labda-8(20),12-dien-16-Oic acid γ-lactone	Generator
Isoandrographolide	MeSH
17-hydro-9-dehydro-Andrographolide	MeSH
Andrographis	PhytoBank
Andrographiside aglycon	PhytoBank
Andrographolid	PhytoBank

Chemical Formula

C₂₀H₃₀O₅

Average Mass

350.4550 Da

Monoisotopic Mass

350.20932 Da

IUPAC Name

(3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-decahydronaphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one

Traditional Name

(3E,4S)-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidene-hexahydro-1H-naphthalen-1-yl]ethylidene}-4-hydroxyoxolan-2-one

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@]1(C([H])([H])[H])[C@]([H])(O[H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])[C@@]([H])(C(=C([H])[H])C([H])([H])C([H])([H])[C@]12[H])C([H])([H])C(\[H])=C1\C(=O)OC([H])([H])[C@@]1([H])O[H]

InChI Identifier

InChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1

InChI Key

BOJKULTULYSRAS-OTESTREVSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ageratina adenophora	Plant	KNApSAcK
Andrographis paniculata	KNApSAcK Database	22123792
Cymbopogon schoenanthus	LOTUS Database	35616633
Ginkgo biloba	LOTUS Database	35616633
human urine	JEOL database	Cui, L., et al, Chem. Pharm. Bull. 52, 772 (2004)
Nicotiana tabacum	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as gamma butyrolactones. These are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Primary alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:65408 )
primary alcohol (CHEBI:65408 )
gamma-lactone (CHEBI:65408 )
carbobicyclic compound (CHEBI:65408 )
labdane diterpenoid (CHEBI:65408 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	225.00 to 226.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	557.32 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	146.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.424 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	1.57	ALOGPS
logP	1.66	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	13.48	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.93 m³·mol⁻¹	ChemAxon
Polarizability	38.17 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

HMDB ID

Not Available

DrugBank ID

DB05767

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023362

Chemspider ID

4477067

KEGG Compound ID

C20214

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Andrographolide

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

65408

Good Scents ID

rw1220141

References

General References

Yanfang Z, Xingping L, Zongde Z, Liren C, Yongmin L: Simultaneous determination of andrographolide and dehydroandrographolide in Andrographis paniculata and Chinese medicinal preparations by microemulsion electrokinetic chromatography. J Pharm Biomed Anal. 2006 Jan 23;40(1):157-61. doi: 10.1016/j.jpba.2005.04.003. [PubMed:15894448 ]
Zhao F, He EQ, Wang L, Liu K: Anti-tumor activities of andrographolide, a diterpene from Andrographis paniculata, by inducing apoptosis and inhibiting VEGF level. J Asian Nat Prod Res. 2008 May-Jun;10(5-6):467-73. doi: 10.1080/10286020801948334. [PubMed:18464090 ]
Abu-Ghefreh AA, Canatan H, Ezeamuzie CI: In vitro and in vivo anti-inflammatory effects of andrographolide. Int Immunopharmacol. 2009 Mar;9(3):313-8. doi: 10.1016/j.intimp.2008.12.002. Epub 2008 Dec 25. [PubMed:19110075 ]
Chen HW, Lin AH, Chu HC, Li CC, Tsai CW, Chao CY, Wang CJ, Lii CK, Liu KL: Inhibition of TNF-alpha-Induced Inflammation by andrographolide via down-regulation of the PI3K/Akt signaling pathway. J Nat Prod. 2011 Nov 28;74(11):2408-13. doi: 10.1021/np200631v. Epub 2011 Oct 25. [PubMed:22026410 ]
Zhou B, Zhang D, Wu X: Biological Activities and Corresponding Sar Analysis of Andrographolide and its Derivatives. Mini Rev Med Chem. 2012 Apr 17. pii: MRMC-EPUB-20120417-019. [PubMed:22512591 ]
Cui, L., et al. (2004). Cui, L., et al, Chem. Pharm. Bull. 52, 772 (2004). Chem. Pharm. Bull..

Showing NP-Card for Andrographolide (NP0026860)

MOL for NP0026860 (Andrographolide)

3D MOL for NP0026860 (Andrographolide)

3D SDF for NP0026860 (Andrographolide)

3D-SDF for NP0026860 (Andrographolide)

PDB for NP0026860 (Andrographolide)

3D PDB for NP0026860 (Andrographolide)

SMILES for NP0026860 (Andrographolide)

INCHI for NP0026860 (Andrographolide)

Structure for NP0026860 (Andrographolide)

3D Structure for NP0026860 (Andrographolide)