NP-MRD: Showing NP-Card for (1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one (NP0312070)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-11 08:32:06 UTC

Updated at

2022-09-11 08:32:07 UTC

NP-MRD ID

NP0312070

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

Description

Physangulide belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. (1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one is found in Physalis angulata. Based on a literature review very few articles have been published on Physangulide.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112210322D          

 37 42  0  0  1  0            999 V2000
    8.3340    4.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274    4.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4966    5.6338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8383    4.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6555    3.9323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    3.3939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5147    3.5067    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3570    3.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6597    2.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6805    0.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8683    0.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1953    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2038    4.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7102    4.9222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0769    5.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7944    5.7429    0.0000 O   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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  1  0  0  0
  8 10  1  1  0  0  0
 11  8  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 19 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 14 32  1  0  0  0  0
 11 32  1  0  0  0  0
 32 33  1  1  0  0  0
  7 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  1  0  0  0
M  END

     RDKit          3D

 79 84  0  0  0  0  0  0  0  0999 V2000
    0.3039   -2.5113   -0.4644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1135   -1.1125   -0.3204 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3726   -0.3653   -1.5431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8299   -0.2230   -1.6953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5594    0.1260   -0.4127 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0438   -0.6856    0.7576 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8003   -0.1417    1.9799 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2272   -0.6087    1.8374 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3993   -1.8045    0.9702 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7944   -0.5775    0.5089 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2746   -0.3976    0.3878 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8313   -1.1650   -0.6578 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7511    1.0157    0.3865 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.5627    1.3183   -0.7261 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5762    1.9415    0.4846 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5349    1.5693   -0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1087    2.4207   -1.2487 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0269    0.1662   -0.5550 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5130   -0.3456   -1.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5953   -0.3810    0.8247 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1450   -0.8704    1.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5632   -0.7305    1.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5172   -0.8019    0.0234 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6675   -1.5072   -0.4561 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8636   -1.7408   -1.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7501   -2.7777    0.1380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9371   -0.7800   -0.0486 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0272    0.6051   -0.6686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4643    1.0877   -0.3663 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8197    2.1982   -1.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3698    0.0616   -0.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4151    1.5528    1.0713 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7566    2.0205    1.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4796    2.6051    1.1239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8766    0.4257    1.8726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1417    0.4441    3.1134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1166   -0.6125    1.3201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2572   -2.9975   -1.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3712   -3.0902    0.4728 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3610   -2.5264   -0.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0103   -0.9610   -2.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1622    0.6135   -1.6421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2970   -1.0659   -2.2428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9935    0.6719   -2.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1981    1.1751   -0.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3237   -1.7353    0.7308 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3478   -0.4982    2.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8294    0.9767    1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8771   -0.6388    2.7352 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7191   -0.8788    1.3131 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8819   -2.1186   -0.4274 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4105    1.2611    1.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8310    2.2620   -0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2024    1.9075    1.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9372    2.9668    0.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5354    0.0983   -2.1204 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8964    0.0885   -2.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5404   -1.4423   -1.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4664    0.7162    0.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1097   -1.9179    2.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0085   -0.2101    2.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9554    0.2423    1.9046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1985   -1.5516    1.9612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6198    0.2960   -0.2988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8116   -0.8529   -2.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3259   -2.6211   -2.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9406   -2.0938   -2.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4917   -2.8702    0.7551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8241   -1.3383   -0.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3223    1.2726   -0.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9348    0.6353   -1.7471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8849    2.4647   -1.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1279    3.0392   -1.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7808    1.7311   -2.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5318   -0.2589   -1.3817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1699    2.7287    0.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4372    1.1603    1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6114    2.5283    2.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8206    3.4135    0.6697 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 26  1  1
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
 10  9  1  6
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  6
 18  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  6
 24 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  1
 29 32  1  0
 32 33  1  0
 32 34  1  6
 32 35  1  0
 35 36  2  0
 35 37  1  0
  2 23  1  0
 37 27  1  0
  2 20  1  0
  5  6  1  0
 10  8  1  0
 18 10  1  0
 25 65  1  0
 25 66  1  0
 25 67  1  0
 26 68  1  0
 23 64  1  6
 22 62  1  0
 22 63  1  0
 21 60  1  0
 21 61  1  0
 20 59  1  6
  6 46  1  6
  7 47  1  0
  7 48  1  0
  8 49  1  1
 11 50  1  1
 12 51  1  0
 13 52  1  1
 14 53  1  0
 15 54  1  0
 15 55  1  0
 19 56  1  0
 19 57  1  0
 19 58  1  0
  5 45  1  1
  4 43  1  0
  4 44  1  0
  3 41  1  0
  3 42  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
 27 69  1  6
 28 70  1  0
 28 71  1  0
 30 72  1  0
 30 73  1  0
 30 74  1  0
 31 75  1  0
 33 76  1  0
 33 77  1  0
 33 78  1  0
 34 79  1  0
M  END


  Mrv1652309112210322D          

 37 42  0  0  1  0            999 V2000
    8.3340    4.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274    4.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4966    5.6338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8383    4.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6555    3.9323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319    3.3939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5147    3.5067    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3570    3.3617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6597    2.3490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7313    1.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0484    0.9486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971    1.4549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3047    0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926    0.3886    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6805    0.2434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8683    0.0982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1953    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    2.2807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7092    2.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9895    3.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2411    1.7952    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5214    2.5711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0532    1.9404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3335    2.7164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1456    2.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6774    2.2309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0373    2.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2038    4.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7102    4.9222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0769    5.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7944    5.7429    0.0000 O   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  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  1  0  0  0
  8 10  1  1  0  0  0
 11  8  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 19 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 15 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 14 32  1  0  0  0  0
 11 32  1  0  0  0  0
 32 33  1  1  0  0  0
  7 34  1  0  0  0  0
 34 35  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0312070

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@](O)([C@H]1CC[C@H]2[C@@H]3C[C@H]4O[C@]44[C@@H](O)[C@@H](O)CC(=O)[C@]4(C)[C@H]3CC[C@]12C)[C@@H]1C[C@@](C)(O)C(C)(O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O9/c1-23-9-8-15-13(10-19-28(37-19)21(31)16(29)11-18(30)25(15,28)3)14(23)6-7-17(23)26(4,34)20-12-24(2,33)27(5,35)22(32)36-20/h13-17,19-21,29,31,33-35H,6-12H2,1-5H3/t13-,14-,15-,16-,17-,19+,20-,21-,23-,24+,25-,26+,27?,28-/m0/s1

> <INCHI_KEY>
OREAQOXKZSQPCV-RJRRLQSFSA-N

> <FORMULA>
C28H42O9

> <MOLECULAR_WEIGHT>
522.635

> <EXACT_MASS>
522.282882932

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
56.157110456364094

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,5S,6S,7R,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2S,4R)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadecan-3-one

> <JCHEM_LOGP>
0.5331825760000009

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.791433158251252

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.499408508524237

> <JCHEM_PKA_STRONGEST_BASIC>
-3.267175746453492

> <JCHEM_POLAR_SURFACE_AREA>
157.05

> <JCHEM_REFRACTIVITY>
129.56849999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,5S,6S,7R,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2S,4R)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadecan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      15.557   9.301   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.051   8.977   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.994  10.516   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      14.631   7.551   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      16.157   7.340   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      13.686   6.335   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      12.161   6.546   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.000   6.275   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.431   4.385   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.137   0.454   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.621   0.183   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.714   5.977   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.580   7.972   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.526   9.188   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      11.344  10.175   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.683  10.720   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   35                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   34                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   32                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   32                                                  
CONECT   15   14   16   29                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17   19                                                       
CONECT   19   18   17   20   27                                             
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   19   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   15   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   14   11   33                                             
CONECT   33   32                                                            
CONECT   34    7   35                                                       
CONECT   35   34    2   36   37                                             
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₄₂O₉

Average Mass

522.6350 Da

Monoisotopic Mass

522.28288 Da

IUPAC Name

(1S,2R,5S,6S,7R,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2S,4R)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadecan-3-one

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@](O)([C@H]1CC[C@H]2[C@@H]3C[C@H]4O[C@]44[C@@H](O)[C@@H](O)CC(=O)[C@]4(C)[C@H]3CC[C@]12C)[C@@H]1C[C@@](C)(O)C(C)(O)C(=O)O1

InChI Identifier

InChI=1S/C28H42O9/c1-23-9-8-15-13(10-19-28(37-19)21(31)16(29)11-18(30)25(15,28)3)14(23)6-7-17(23)26(4,34)20-12-24(2,33)27(5,35)22(32)36-20/h13-17,19-21,29,31,33-35H,6-12H2,1-5H3/t13-,14-,15-,16-,17-,19+,20-,21-,23-,24+,25-,26+,27?,28-/m0/s1

InChI Key

OREAQOXKZSQPCV-RJRRLQSFSA-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 angulata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
5,6-epoxysteroid
Oxepane
Delta_valerolactone
Delta valerolactone
Oxane
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
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
logP	0.53	ChemAxon
pKa (Strongest Acidic)	11.5	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	157.05 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	129.57 m³·mol⁻¹	ChemAxon
Polarizability	56.16 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

C00057016

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102061067

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one (NP0312070)

MOL for NP0312070 ((1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D MOL for NP0312070 ((1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D SDF for NP0312070 ((1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D-SDF for NP0312070 ((1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

PDB for NP0312070 ((1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D PDB for NP0312070 ((1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

SMILES for NP0312070 ((1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

INCHI for NP0312070 ((1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

Structure for NP0312070 ((1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D Structure for NP0312070 ((1s,2r,5s,6s,7r,9r,11s,12s,15s,16s)-15-[(1r)-1-[(2s,4r)-4,5-dihydroxy-4,5-dimethyl-6-oxooxan-2-yl]-1-hydroxyethyl]-5,6-dihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)