NP-MRD: Showing NP-Card for (1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde (NP0229587)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 09:43:10 UTC

Updated at

2022-09-06 09:43:10 UTC

NP-MRD ID

NP0229587

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde

Description

Cyclamiretin A belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde is found in Androsace umbellata, Cyclamen balearicum and Cyclamen hederifolium. (1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde was first documented in 2005 (PMID: 15621596). Based on a literature review a significant number of articles have been published on Cyclamiretin A (PMID: 21590653) (PMID: 28173950) (PMID: 26949015) (PMID: 25521557) (PMID: 18985500) (PMID: 17665849).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062211432D          

 34 39  0  0  1  0            999 V2000
    4.3080    1.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4308    0.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2129    0.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8251   -0.2391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6499   -0.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948   -0.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5700   -0.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757   -0.1975    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7453   -0.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6060    0.5063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2117    1.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9566    0.5479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5684    1.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -0.1767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9282   -0.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1019   -0.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6520   -0.1730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0698   -0.7035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971   -0.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5710    0.6062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2701    0.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2403   -0.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5114   -1.0428    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0414   -1.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0185   -1.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7085   -2.4580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1877   -0.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1579    0.2198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1472    1.3601    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5662    2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131    1.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1152    0.5834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0664    1.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  1  0  0  0
 26 27  2  0  0  0  0
 24 28  1  0  0  0  0
 29 28  1  1  0  0  0
 21 29  1  0  0  0  0
 18 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 18 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END

     RDKit          3D

 82 87  0  0  0  0  0  0  0  0999 V2000
    5.4948   -0.9471    0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7767    0.2512    0.6921 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1208    0.3228    2.1941 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2036    1.5408    0.0434 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1545    1.3230   -0.9825 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0728    2.3973   -0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9740    1.7697   -1.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610    0.3263   -0.6888 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1850   -0.5332   -1.7848 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2872    0.1720    0.6380 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8484   -1.0273    1.4315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3603   -0.9497    1.6208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086   -0.8188    0.3243 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6746   -2.1820   -0.2924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734    0.2264   -0.5933 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4811    0.2050   -1.9254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9877    0.3750   -1.7450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5961   -0.4443   -0.6441 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6794   -1.7987   -1.0594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7928   -2.3687   -0.4894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5248   -1.2629    0.2766 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.9909   -1.3142    0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6625    0.0239    0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0669    1.0759   -0.6274 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.7526    2.3765   -0.4122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2476    0.6598   -2.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2585    1.4432   -2.9794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5586    1.1774   -0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0327   -0.1323   -0.5999 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9600   -1.2368    1.6510 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5240   -0.1849    2.3709 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4754   -1.2730    1.6737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8316   -0.3895    0.6368 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8695    1.0069    1.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2098   -0.6333   -0.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8326   -1.7734   -0.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1830   -1.4288    0.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3416    0.8822    2.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3251   -0.6815    2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1009    0.8686    2.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7907    2.1586    0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0673    1.2259   -0.6125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4982    3.2224   -1.0208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6743    2.9358    0.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1850    1.8334   -2.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0598    2.4231   -0.9940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6690   -0.1853   -2.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0185   -1.5961   -1.7231 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2559   -0.3665   -2.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9266    1.0574    1.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2287   -1.9809    1.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2976   -0.8896    2.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0609   -1.9429    2.0754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1501   -0.2149    2.3848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0260   -2.9258    0.1301 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5895   -2.2358   -1.3707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6797   -2.6515   -0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8428    1.2221   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8432    1.1300   -2.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6899   -0.6218   -2.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2156    1.4452   -1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4937    0.0762   -2.6988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4324   -2.8218   -1.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5028   -3.1687    0.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3089   -1.8533   -0.7662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3933   -1.9372    1.0016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6279    0.3365    1.3349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7268   -0.1134    0.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8435    2.1792   -0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3530    2.9713    0.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7345    2.9509   -1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3803   -0.3933   -2.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5358    1.5637    0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1717    1.9191   -1.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4282   -0.4157   -1.6319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3389   -2.1705    2.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2700   -0.2655    3.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1636   -0.8599    2.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1436   -2.3057    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1532    1.7729    0.4622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0699    1.3419    1.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6114    1.1069    2.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 21 22  1  1
 21 20  1  0
 20 19  1  0
 18 19  1  6
 18 17  1  0
 17 16  1  0
 16 15  1  0
 15  8  1  0
  8  9  1  6
  8  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 33  1  0
 33 34  1  1
 33 32  1  0
 32 30  1  0
 30 31  1  0
 18 29  1  0
 29 28  1  0
 24 26  1  6
 26 27  2  0
 28 24  1  0
 30 21  1  0
 29 21  1  0
 33 18  1  0
 13 15  1  0
 10  8  1  0
 25 69  1  0
 25 70  1  0
 25 71  1  0
 23 67  1  0
 23 68  1  0
 22 65  1  0
 22 66  1  0
 20 63  1  0
 20 64  1  0
 17 61  1  0
 17 62  1  0
 16 59  1  0
 16 60  1  0
 15 58  1  1
  9 47  1  0
  9 48  1  0
  9 49  1  0
  7 45  1  0
  7 46  1  0
  6 43  1  0
  6 44  1  0
  4 41  1  1
  5 42  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
 10 50  1  1
 11 51  1  0
 11 52  1  0
 12 53  1  0
 12 54  1  0
 14 55  1  0
 14 56  1  0
 14 57  1  0
 34 80  1  0
 34 81  1  0
 34 82  1  0
 32 78  1  0
 32 79  1  0
 30 76  1  1
 31 77  1  0
 29 75  1  6
 28 73  1  0
 28 74  1  0
 26 72  1  0
M  END


  Mrv1652309062211432D          

 34 39  0  0  1  0            999 V2000
    4.3080    1.3014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4308    0.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2129    0.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8251   -0.2391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6499   -0.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948   -0.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5700   -0.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757   -0.1975    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7453   -0.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6060    0.5063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2117    1.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9566    0.5479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5684    1.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -0.1767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9282   -0.8961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1019   -0.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6520   -0.1730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0698   -0.7035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971   -0.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5710    0.6062    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2701    0.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2403   -0.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5114   -1.0428    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0414   -1.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0185   -1.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7085   -2.4580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1877   -0.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1579    0.2198    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1472    1.3601    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5662    2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7131    1.3658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1152    0.5834    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0664    1.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 21 20  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  1  0  0  0
 26 27  2  0  0  0  0
 24 28  1  0  0  0  0
 29 28  1  1  0  0  0
 21 29  1  0  0  0  0
 18 29  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 18 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0229587

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(CC[C@]23CO[C@@]4(CC[C@@H]5[C@@]6(C)CC[C@H](O)C(C)(C)[C@@H]6CC[C@@]5(C)[C@]4(C)C[C@H]2O)[C@@H]3C1)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-24(2)19-7-11-27(5)20(26(19,4)10-9-22(24)32)8-12-30-21-15-25(3,17-31)13-14-29(21,18-34-30)23(33)16-28(27,30)6/h17,19-23,32-33H,7-16,18H2,1-6H3/t19-,20+,21+,22-,23+,25-,26-,27+,28-,29+,30-/m0/s1

> <INCHI_KEY>
UBWMMEPLQFWYCH-GFRLSDCRSA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.71

> <EXACT_MASS>
472.355260026

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
55.543439539843874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,20S)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosane-20-carbaldehyde

> <JCHEM_LOGP>
4.410571976000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.489433390166933

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.595891365941132

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8349239673202166

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
133.0803

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,20S)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosane-20-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       8.042   2.429   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.271   0.906   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.731   1.396   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.007  -0.446   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.546  -0.485   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.204  -1.760   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.664  -1.721   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.928  -0.369   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.125  -1.683   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.731   0.945   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.995   2.298   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.456   2.337   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.652   1.023   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.928   2.382   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.388  -0.330   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.599  -1.673   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.057  -1.655   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.217  -0.323   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.130  -1.313   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.488  -0.424   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.066   1.132   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.371   0.314   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.315  -1.225   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.955  -1.946   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.077  -3.090   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.901  -3.161   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.323  -4.588   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       0.350  -1.129   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.295   0.410   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.275   2.539   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.057   3.866   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.331   2.549   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.082   1.089   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.991   2.626   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   10                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   15                                             
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   33                                             
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   29   33                                             
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   29   30                                             
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26   28                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   24   29                                                       
CONECT   29   28   21   18                                                  
CONECT   30   21   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   18   13   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₈O₄

Average Mass

472.7100 Da

Monoisotopic Mass

472.35526 Da

IUPAC Name

(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,20S)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosane-20-carbaldehyde

Traditional Name

(1S,2R,4S,5R,8R,10S,13R,14R,17S,18R,20S)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracosane-20-carbaldehyde

CAS Registry Number

Not Available

SMILES

C[C@@]1(CC[C@]23CO[C@@]4(CC[C@@H]5[C@@]6(C)CC[C@H](O)C(C)(C)[C@@H]6CC[C@@]5(C)[C@]4(C)C[C@H]2O)[C@@H]3C1)C=O

InChI Identifier

InChI=1S/C30H48O4/c1-24(2)19-7-11-27(5)20(26(19,4)10-9-22(24)32)8-12-30-21-15-25(3,17-31)13-14-29(21,18-34-30)23(33)16-28(27,30)6/h17,19-23,32-33H,7-16,18H2,1-6H3/t19-,20+,21+,22-,23+,25-,26-,27+,28-,29+,30-/m0/s1

InChI Key

UBWMMEPLQFWYCH-GFRLSDCRSA-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
Androsace umbellata	LOTUS Database	35616633
Cyclamen balearicum	LOTUS Database	35616633
Cyclamen hederifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Oxepane
Cyclic alcohol
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Ether
Dialkyl ether
Oxacycle
Organic oxide
Aldehyde
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	4.41	ChemAxon
pKa (Strongest Acidic)	14.6	ChemAxon
pKa (Strongest Basic)	-0.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	133.08 m³·mol⁻¹	ChemAxon
Polarizability	55.54 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

10264479

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12305336

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li YF, Hu LH, Lou FC, Li J, Shen Q: PTP1B inhibitors from Ardisia japonica. J Asian Nat Prod Res. 2005 Feb;7(1):13-8. doi: 10.1080/10286020310001596033. [PubMed:15621596 ]
Avula B, Wang YH, Ali Z, Smillie TJ, Khan IA: Quantitative determination of triperpene saponins and alkenated-phenolics from Labisia pumila using an LC-UV/ELSD method and confirmation by LC-ESI-TOF. Planta Med. 2011 Oct;77(15):1742-8. doi: 10.1055/s-0030-1271037. Epub 2011 May 17. [PubMed:21590653 ]
Dai LM, Huang RZ, Zhang B, Hua J, Wang HS, Liang D: Cytotoxic triterpenoid saponins from Lysimachia foenum-graecum. Phytochemistry. 2017 Apr;136:165-174. doi: 10.1016/j.phytochem.2017.01.021. Epub 2017 Feb 5. [PubMed:28173950 ]
Liu DL, Zhang X, Zhao Y, Wang NL, Yao XS: Three new triterpenoid saponins from the roots of Ardisia crenata and their cytotoxic activities. Nat Prod Res. 2016 Dec;30(23):2694-2703. doi: 10.1080/14786419.2016.1146889. Epub 2016 Mar 7. [PubMed:26949015 ]
Dong XZ, Xie TT, Zhou XJ, Mu LH, Zheng XL, Guo DH, Liu P, Ge XY: AG4, a compound isolated from Radix Ardisiae Gigantifoliae, induces apoptosis in human nasopharyngeal cancer CNE cells through intrinsic and extrinsic apoptosis pathways. Anticancer Drugs. 2015 Mar;26(3):331-42. doi: 10.1097/CAD.0000000000000193. [PubMed:25521557 ]
Wen P, Zhang XM, Yang Z, Wang NL, Yao XS: Four new triterpenoid saponins from Ardisia gigantifolia Stapf. and their cytotoxic activity. J Asian Nat Prod Res. 2008 Sep-Oct;10(9-10):873-80. doi: 10.1080/10286020802144719. [PubMed:18985500 ]
Podolak I, Janeczko Z, Galanty A, Michalik M, Trojanowska D: A triterpene saponin from Lysimachia thyrsiflora L. Acta Pol Pharm. 2007 Jan-Feb;64(1):39-43. [PubMed:17665849 ]
Liang B, Tian JK, Xu LZ, Yang SL: Triterpenoid saponins from Lysimachia davurica. Chem Pharm Bull (Tokyo). 2006 Oct;54(10):1380-3. doi: 10.1248/cpb.54.1380. [PubMed:17015973 ]
LOTUS database [Link]

Showing NP-Card for (1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde (NP0229587)

MOL for NP0229587 ((1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde)

3D MOL for NP0229587 ((1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde)

3D SDF for NP0229587 ((1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde)

3D-SDF for NP0229587 ((1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde)

PDB for NP0229587 ((1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde)

3D PDB for NP0229587 ((1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde)

SMILES for NP0229587 ((1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde)

INCHI for NP0229587 ((1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde)

Structure for NP0229587 ((1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde)

3D Structure for NP0229587 ((1s,2r,4s,5r,8r,10s,13r,14r,17s,18r,20s)-2,10-dihydroxy-4,5,9,9,13,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracosane-20-carbaldehyde)