NP-MRD: Showing NP-Card for (1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid (NP0146607)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 02:02:20 UTC

Updated at

2022-09-02 02:02:21 UTC

NP-MRD ID

NP0146607

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid

Description

Celastolide belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Celastolide 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. (1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid is found in Tripterygium hypoglaucum. Based on a literature review very few articles have been published on celastolide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022204022D          

 35 40  0  0  1  0            999 V2000
    2.6497   -1.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375   -1.0925    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1864   -1.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795   -2.1922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6619   -0.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1055   -0.0612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8854    0.7339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4639    1.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2625    1.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4826    0.3201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2813    0.1132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0611    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8598    0.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6584    0.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8785   -0.3006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4570    0.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6772   -0.5075    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2557    0.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0543   -0.1263    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1194    0.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8755   -0.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2180    0.7030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3543   -0.7194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2744   -0.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6959   -1.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8973   -1.3026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1174   -2.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3188   -1.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5202   -1.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000   -0.8888    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7215   -1.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5014   -0.6819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9229   -1.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1243   -1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9041   -0.2681    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 15 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 11 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 35 34  1  1  0  0  0
  6 35  1  0  0  0  0
 10 35  1  0  0  0  0
  2 35  1  0  0  0  0
M  END

     RDKit          3D

 81 86  0  0  0  0  0  0  0  0999 V2000
   -3.6425    2.2050   -1.9785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4753    1.7753   -0.5562 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6251    2.3353    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7013    3.4784    0.7765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6333    1.4024    0.3358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2183    0.2964   -0.3987 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7640   -0.8639    0.0982 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5782   -0.7629    1.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1041   -1.1157    1.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1763   -0.1645    0.9533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7829   -0.7343    0.9861 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7645   -2.1318    1.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8834    0.0714    1.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5628   -0.1072    1.6725 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9708    0.0459    0.2393 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5962    1.4082   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4551   -0.2393    0.1159 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1917    0.5959    1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6307    0.8529    0.7691 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4562   -0.3466    1.1957 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0784    1.9878    1.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5002    3.0663    1.2107 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0130    1.8117    3.0281 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8801    1.2754   -0.6297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7572    1.0722   -1.5781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9352   -0.1949   -1.2859 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9494   -1.3403   -1.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913   -0.2766   -2.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5498   -0.7275   -2.0221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458   -1.0330   -0.5492 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6574   -2.4142   -0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2204   -0.7375   -0.3725 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1251   -1.4607   -1.3054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3039   -0.5334   -1.5512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6794    0.2862   -0.3537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3699    1.6310   -2.5463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0328    3.2651   -1.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6690    2.2918   -2.5261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5932    2.1997   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5784    0.4183   -1.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1567   -1.5448    1.9768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8289    0.2221    1.8789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0086   -2.1529    1.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9913   -0.9529    2.8213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1648    0.7577    1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385   -2.3397    2.0539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3702   -2.1253    2.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1592   -2.9153    1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0561   -0.2881    3.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2270    1.1379    1.9916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1060    0.6401    2.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8807   -1.1019    2.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3139    1.5218   -1.2686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2634    1.8566    0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4126    2.1763   -0.0741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5703   -1.3048    0.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7311    1.5790    1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101    0.0814    2.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2297   -0.5568    0.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8228   -1.2401    1.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0311   -0.1683    2.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4811    2.3992    3.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8151    0.7433   -0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1690    2.3667   -0.7113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2192    0.8574   -2.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1130    1.9468   -1.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6856   -1.8973   -2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9719   -1.0091   -1.5850 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8877   -2.0672   -0.6485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8186    0.7005   -2.9252 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3126   -0.9421   -3.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2371   -0.0394   -2.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3057   -1.6992   -2.5566 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1250   -2.6889    0.6400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2413   -3.0888   -0.4254 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616   -2.7969   -1.0939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2401    0.3472   -0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5501   -2.4026   -0.9248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7058   -1.6877   -2.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9340    0.1989   -2.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1008   -1.1107   -2.0077 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 35  1  0
 35 34  1  6
 34 33  1  0
 33 32  1  0
 32 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
 26 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  1
 19 21  1  1
 21 23  1  0
 21 22  2  0
 35  2  1  0
 30 32  1  0
 35  6  1  0
 30 15  1  0
 11 10  1  0
 26 17  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  1
  6 40  1  6
  8 41  1  0
  8 42  1  0
  9 43  1  0
  9 44  1  0
 10 45  1  1
 34 80  1  0
 34 81  1  0
 33 78  1  0
 33 79  1  0
 32 77  1  6
 12 46  1  0
 12 47  1  0
 12 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 16 53  1  0
 16 54  1  0
 16 55  1  0
 17 56  1  1
 18 57  1  0
 18 58  1  0
 20 59  1  0
 20 60  1  0
 20 61  1  0
 24 63  1  0
 24 64  1  0
 25 65  1  0
 25 66  1  0
 27 67  1  0
 27 68  1  0
 27 69  1  0
 28 70  1  0
 28 71  1  0
 29 72  1  0
 29 73  1  0
 31 74  1  0
 31 75  1  0
 31 76  1  0
 23 62  1  0
M  END


  Mrv1652309022204022D          

 35 40  0  0  1  0            999 V2000
    2.6497   -1.5351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375   -1.0925    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1864   -1.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795   -2.1922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6619   -0.7568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1055   -0.0612    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8854    0.7339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4639    1.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2625    1.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4826    0.3201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2813    0.1132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0611    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8598    0.7014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6584    0.4945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8785   -0.3006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4570    0.2876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6772   -0.5075    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2557    0.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0543   -0.1263    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1194    0.6962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8755   -0.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2180    0.7030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3543   -0.7194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2744   -0.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6959   -1.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8973   -1.3026    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1174   -2.0977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3188   -1.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5202   -1.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000   -0.8888    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7215   -1.4770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5014   -0.6819    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9229   -1.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1243   -1.0632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9041   -0.2681    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  6  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 19 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 17 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 15 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 11 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 35 34  1  1  0  0  0
  6 35  1  0  0  0  0
 10 35  1  0  0  0  0
  2 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146607

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O5/c1-18-22(31)35-24-30(18)9-7-19-27(4,20(30)8-16-34-24)13-15-29(6)21-17-26(3,23(32)33)11-10-25(21,2)12-14-28(19,29)5/h18-21,24H,7-17H2,1-6H3,(H,32,33)/t18-,19-,20-,21+,24-,25+,26+,27+,28+,29-,30-/m0/s1

> <INCHI_KEY>
MHUNAMWYXWYEMX-PLTLGRIDSA-N

> <FORMULA>
C30H46O5

> <MOLECULAR_WEIGHT>
486.693

> <EXACT_MASS>
486.334524581

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
55.33021866439596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,8R,10R,11S,14R,15S,19S,22R,23R)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{19,23}]pentacosane-8-carboxylic acid

> <ALOGPS_LOGP>
5.68

> <JCHEM_LOGP>
6.375176283333332

> <ALOGPS_LOGS>
-6.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.773280222311161

> <JCHEM_PKA_STRONGEST_BASIC>
-4.32454488704718

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
132.48349999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.99e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,8R,10R,11S,14R,15S,19S,22R,23R)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{19,23}]pentacosane-8-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       4.946  -2.866   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.430  -2.039   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.215  -2.601   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.828  -4.092   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.236  -1.413   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.064  -0.114   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.653   1.370   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.733   2.468   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.223   2.082   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.634   0.598   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.125   0.211   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.714   1.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.205   1.309   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.696   0.923   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.107  -0.561   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.186   0.537   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.597  -0.947   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.677   0.151   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.168  -0.236   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.290   1.300   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.701  -0.089   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      15.340   1.312   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      15.595  -1.343   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      13.579  -1.720   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.499  -2.818   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.008  -2.432   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.419  -3.916   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.928  -3.530   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.438  -3.143   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.027  -1.659   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.947  -2.757   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.536  -1.273   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.456  -2.371   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.965  -1.985   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.554  -0.500   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   35                                                  
CONECT   11   10   12   13   32                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   30                                             
CONECT   16   15                                                            
CONECT   17   15   18   26                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21   24                                             
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   17   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   15   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   11   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    6   10    2                                             
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Value	Source
Celastoside	ChEBI

Chemical Formula

C₃₀H₄₆O₅

Average Mass

486.6930 Da

Monoisotopic Mass

486.33452 Da

IUPAC Name

(1S,2R,5S,8R,10R,11S,14R,15S,19S,22R,23R)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{19,23}]pentacosane-8-carboxylic acid

Traditional Name

(1S,2R,5S,8R,10R,11S,14R,15S,19S,22R,23R)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0^{2,11}.0^{5,10}.0^{15,23}.0^{19,23}]pentacosane-8-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H46O5/c1-18-22(31)35-24-30(18)9-7-19-27(4,20(30)8-16-34-24)13-15-29(6)21-17-26(3,23(32)33)11-10-25(21,2)12-14-28(19,29)5/h18-21,24H,7-17H2,1-6H3,(H,32,33)/t18-,19-,20-,21+,24-,25+,26+,27+,28+,29-,30-/m0/s1

InChI Key

MHUNAMWYXWYEMX-PLTLGRIDSA-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
Tripterygium hypoglaucum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Furopyran
Dicarboxylic acid or derivatives
Gamma butyrolactone
Pyran
Oxane
Furan
Oxolane
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid
Acetal
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
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
logP	5.68	ALOGPS
logP	6.38	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	4.77	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	132.48 m³·mol⁻¹	ChemAxon
Polarizability	55.33 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58827398

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101936042

PDB ID

Not Available

ChEBI ID

132344

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid (NP0146607)

MOL for NP0146607 ((1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid)

3D MOL for NP0146607 ((1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid)

3D SDF for NP0146607 ((1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid)

3D-SDF for NP0146607 ((1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid)

PDB for NP0146607 ((1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid)

3D PDB for NP0146607 ((1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid)

SMILES for NP0146607 ((1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid)

INCHI for NP0146607 ((1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid)

Structure for NP0146607 ((1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid)

3D Structure for NP0146607 ((1s,2r,5s,8r,10r,11s,14r,15s,19s,22r,23r)-2,5,8,11,14,22-hexamethyl-21-oxo-18,20-dioxahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁹,²³]pentacosane-8-carboxylic acid)