NP-MRD: Showing NP-Card for (1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone (NP0247204)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 08:57:35 UTC

Updated at

2022-09-07 08:57:35 UTC

NP-MRD ID

NP0247204

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone

Description

Physalin L belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed). (1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone is found in Physalis lagascae and Physalis minima. (1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone was first documented in 2010 (PMID: 21046739). Based on a literature review a small amount of articles have been published on Physalin L (PMID: 29096922) (PMID: 22197662) (PMID: 28273367).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072210572D          

 38 44  0  0  1  0            999 V2000
    0.0885    0.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068    0.1607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6433   -0.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3640    0.1363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6114   -1.1192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1445   -1.5281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5231   -0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731   -0.2305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2520    0.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6299   -0.6266    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4690   -1.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9713   -1.8016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2498   -0.4229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5931    0.0764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4543   -1.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6423   -1.6939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8611   -2.0415    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1547   -2.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9776   -2.8897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -3.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015   -3.8496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2163   -2.3797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6016   -3.1092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0753   -2.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851   -1.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7111   -1.0375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1387   -0.4435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3669    0.3493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7944    0.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676    0.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7401   -0.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408    0.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1132   -0.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8850   -1.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0843   -1.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8561   -2.2256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5118   -0.8388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2836   -1.6316    0.0000 C   0  0  0  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
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 16 15  1  6  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 16 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
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 13  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 31 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END

     RDKit          3D

 70 76  0  0  0  0  0  0  0  0999 V2000
   -4.5603    2.0296   -1.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7070    0.8316   -0.8388 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6015   -0.3666   -1.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5968   -0.3404   -1.8042 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3236   -1.5493   -0.3424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5649   -1.3734    0.8650 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9750   -0.0682    1.4455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2918    1.0053    0.5807 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8365    2.3369    1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8644    0.9413    0.8876 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9980    1.6508   -0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3197    2.4298   -1.0104 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2489    1.0133    0.2606 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3115    1.5108    1.5544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2535   -0.2626    0.0498 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2263   -0.4012    0.9855 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1293   -1.5241    0.5279 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8765   -1.8699   -0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6429   -2.6312    1.2864 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2100   -2.1205    2.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3738   -2.6050    3.6105 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4820   -0.8477    2.1755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7176   -0.0911    3.3275 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0069   -1.1022    2.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6192   -1.3468    0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1482   -0.3978   -0.2144 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5323    1.0165   -0.3079 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7355    1.5676   -1.6992 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6013    1.4053   -2.4940 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9443    1.0095   -2.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8250    0.2146   -1.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9883   -0.2794   -2.5410 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5756   -1.4491   -2.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0045   -2.2811   -1.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4580   -1.4081   -0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7465   -1.7402    1.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6313   -0.2278   -0.3664 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1889    0.9468    0.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6105    1.8915   -0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1201    2.9820   -0.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5877    1.9973   -2.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8732    0.7873   -1.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9546   -2.1791    1.5489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0675    0.0236    1.4179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5410    0.0373    2.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1336    3.1153    0.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049    2.2637    2.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8782    2.4996    0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603    1.5303    1.8218 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0052    2.1865    1.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8385   -2.1176   -1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3393   -1.0534   -1.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2235   -2.7706   -1.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0789   -0.0764    3.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1160   -2.0848    2.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6400   -0.4831    2.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9766   -2.1774    0.2662 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5261   -2.0213    0.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8112   -0.7997   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2618    1.6213    0.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8847    2.6638   -1.6145 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9146    1.0365   -3.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1238    1.2986   -3.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4189    0.3099   -3.3402 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4331   -1.8166   -2.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8234   -2.9247   -0.8167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2278   -2.9553   -1.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7872    0.9857    1.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1986    1.8907   -0.1165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2905    0.7135    0.5924 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  1
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  1
 13 15  1  0
 16 15  1  6
 16 17  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  1  0
 35 36  2  0
 35 37  1  0
 37 38  1  1
  8  2  1  0
 16 10  1  0
 22 16  1  0
 37 26  1  0
 17  6  1  0
 37 31  1  0
 27 13  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  6
  6 43  1  1
  7 44  1  0
  7 45  1  0
  9 46  1  0
  9 47  1  0
  9 48  1  0
 10 49  1  1
 14 50  1  0
 18 51  1  0
 18 52  1  0
 18 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  6
 27 60  1  1
 28 61  1  1
 29 62  1  0
 30 63  1  0
 32 64  1  0
 33 65  1  0
 34 66  1  0
 34 67  1  0
 38 68  1  0
 38 69  1  0
 38 70  1  0
M  END


  Mrv1652309072210572D          

 38 44  0  0  1  0            999 V2000
    0.0885    0.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068    0.1607    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6433   -0.2653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3640    0.1363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6114   -1.1192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1445   -1.5281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5231   -0.8576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8731   -0.2305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2520    0.5024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6299   -0.6266    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4690   -1.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9713   -1.8016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2498   -0.4229    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5931    0.0764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4543   -1.0638    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6423   -1.6939    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8611   -2.0415    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1547   -2.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9776   -2.8897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -3.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015   -3.8496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2163   -2.3797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6016   -3.1092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0753   -2.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6851   -1.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7111   -1.0375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1387   -0.4435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3669    0.3493    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7944    0.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1676    0.5481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7401   -0.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5408    0.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1132   -0.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8850   -1.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0843   -1.4328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8561   -2.2256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5118   -0.8388    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2836   -1.6316    0.0000 C   0  0  0  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
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 16 15  1  6  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 16 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
 26 25  1  1  0  0  0
 26 27  1  0  0  0  0
 27 13  1  6  0  0  0
 27 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 31 37  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0247204

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C(=O)O[C@@H]2C[C@@]1(C)[C@@H]1C(=O)[C@@]3(O)O[C@]11[C@@]2(C)OC(=O)[C@@]1(O)CC[C@H]1[C@H]3[C@H](O)C=C2C=CCC(=O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H32O10/c1-12-21(32)36-17-11-23(12,2)19-20(31)27(35)18-14(24(3)13(10-15(18)29)6-5-7-16(24)30)8-9-26(34)22(33)37-25(17,4)28(19,26)38-27/h5-6,10,12,14-15,17-19,29,34-35H,7-9,11H2,1-4H3/t12-,14+,15-,17-,18+,19+,23-,24+,25+,26+,27+,28+/m1/s1

> <INCHI_KEY>
CUSXWWXXAPEFHY-AWZDPXLZSA-N

> <FORMULA>
C28H32O10

> <MOLECULAR_WEIGHT>
528.554

> <EXACT_MASS>
528.19954723

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.85007059205597

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,3R,5S,6S,7R,14R,15S,18R,21S,22R,25S)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1^{2,5}.0^{3,18}.0^{3,21}.0^{6,15}.0^{9,14}]heptacosa-8,10-diene-13,19,24,27-tetrone

> <JCHEM_LOGP>
1.3745110146666661

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.728745100624009

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.635092385797014

> <JCHEM_PKA_STRONGEST_BASIC>
-3.081795036922199

> <JCHEM_POLAR_SURFACE_AREA>
156.66000000000003

> <JCHEM_REFRACTIVITY>
128.615

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,3R,5S,6S,7R,14R,15S,18R,21S,22R,25S)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1^{2,5}.0^{3,18}.0^{3,21}.0^{6,15}.0^{9,14}]heptacosa-8,10-diene-13,19,24,27-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       0.165   1.840   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.199   0.300   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.201  -0.495   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.546   0.255   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.141  -2.089   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.270  -2.852   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.976  -1.601   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.630  -0.430   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.337   0.938   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.042  -1.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.609  -2.141   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.546  -3.363   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.200  -0.789   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.974   0.143   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.715  -1.986   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.066  -3.162   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.607  -3.811   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.289  -4.606   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.825  -5.394   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.334  -5.763   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.923  -7.186   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.137  -4.442   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.856  -5.804   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.740  -4.527   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.879  -3.470   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.927  -1.937   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.859  -0.828   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.285   0.652   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.216   1.761   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.780   1.023   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.848  -0.086   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.343   0.285   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.411  -0.824   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.985  -2.304   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       9.491  -2.675   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.065  -4.154   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.422  -1.566   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       7.996  -3.046   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    2    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   27                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10   17   22                                             
CONECT   17   16    6   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   16   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   37                                                  
CONECT   27   26   13   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   31   26   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂O₁₀

Average Mass

528.5540 Da

Monoisotopic Mass

528.19955 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1C(=O)O[C@@H]2C[C@@]1(C)[C@@H]1C(=O)[C@@]3(O)O[C@]11[C@@]2(C)OC(=O)[C@@]1(O)CC[C@H]1[C@H]3[C@H](O)C=C2C=CCC(=O)[C@]12C

InChI Identifier

InChI=1S/C28H32O10/c1-12-21(32)36-17-11-23(12,2)19-20(31)27(35)18-14(24(3)13(10-15(18)29)6-5-7-16(24)30)8-9-26(34)22(33)37-25(17,4)28(19,26)38-27/h5-6,10,12,14-15,17-19,29,34-35H,7-9,11H2,1-4H3/t12-,14+,15-,17-,18+,19+,23-,24+,25+,26+,27+,28+/m1/s1

InChI Key

CUSXWWXXAPEFHY-AWZDPXLZSA-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
Physalis lagascae	LOTUS Database	35616633
Physalis minima	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Physalins and derivatives

Direct Parent

Physalins and derivatives

Alternative Parents

Substituents

Physalin skeleton
Cyclohexenone
Delta_valerolactone
Delta valerolactone
Oxane
Gamma butyrolactone
3-furanone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00056862

Chemspider ID

84393739

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101637227

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kranjc E, Albreht A, Vovk I, Glavnik V: High performance thin-layer chromatography-mass spectrometry enables reliable analysis of physalins in different plant parts of Physalis alkekengi L. J Chromatogr A. 2017 Dec 1;1526:137-150. doi: 10.1016/j.chroma.2017.09.070. Epub 2017 Sep 29. [PubMed:29096922 ]
Ji L, Yuan Y, Luo L, Chen Z, Ma X, Ma Z, Cheng L: Physalins with anti-inflammatory activity are present in Physalis alkekengi var. franchetii and can function as Michael reaction acceptors. Steroids. 2012 Apr;77(5):441-7. doi: 10.1016/j.steroids.2011.11.016. Epub 2011 Dec 9. [PubMed:22197662 ]
Cheng X, Zhang C, Chou G, Wang Z: [Investigation on quality standard of Franchet groundcherry]. Zhongguo Zhong Yao Za Zhi. 2010 Aug;35(16):2103-5. [PubMed:21046739 ]
Guo Y, Liu H, Ding L, Oppong M, Pan G, Qiu F: LC-MS/MS method for simultaneous determination of flavonoids and physalins in rat plasma: Application to pharmacokinetic study after oral administration of Physalis alkekengi var. franchetii (Chinese lantern) extract. Biomed Chromatogr. 2017 Oct;31(10). doi: 10.1002/bmc.3970. Epub 2017 May 2. [PubMed:28273367 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone (NP0247204)

MOL for NP0247204 ((1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone)

3D MOL for NP0247204 ((1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone)

3D SDF for NP0247204 ((1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone)

3D-SDF for NP0247204 ((1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone)

PDB for NP0247204 ((1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone)

3D PDB for NP0247204 ((1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone)

SMILES for NP0247204 ((1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone)

INCHI for NP0247204 ((1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone)

Structure for NP0247204 ((1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone)

3D Structure for NP0247204 ((1s,2s,3r,5s,6s,7r,14r,15s,18r,21s,22r,25s)-5,7,18-trihydroxy-1,14,21,25-tetramethyl-4,20,23-trioxaheptacyclo[20.3.1.1²,⁵.0³,¹⁸.0³,²¹.0⁶,¹⁵.0⁹,¹⁴]heptacosa-8,10-diene-13,19,24,27-tetrone)