NP-MRD: Showing NP-Card for [(1s,2r,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate (NP0256520)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 21:22:47 UTC

Updated at

2022-09-07 21:22:48 UTC

NP-MRD ID

NP0256520

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,2r,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate

Description

Cyclocalopin D belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. [(1s,2r,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate is found in Boletus coniferarum. Based on a literature review very few articles have been published on Cyclocalopin D.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072223222D          

 36 40  0  0  1  0            999 V2000
   -2.7793    0.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1884    0.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3943    0.5749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3914   -0.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8005   -1.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0064   -0.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4031   -1.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -2.2260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3887   -2.4588    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9860   -1.8898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7775   -2.1226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3749   -1.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1663   -1.7864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9716   -2.9245    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7631   -3.1573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3743   -3.4935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5684   -4.2953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5828   -3.2607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9854   -3.8297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022   -1.1510    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0178   -1.7003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5866   -0.2993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1589   -0.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8144    0.0627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3002    0.7890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5665    0.5669    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5575    1.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3863    0.7961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8801    0.1239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7011    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1819    0.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0414   -0.7088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5606   -1.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7396   -1.2982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2589   -1.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3994   -0.5466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  6  0  0  0
  7 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 24 23  1  6  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 29  1  6  0  0  0
 22 36  1  0  0  0  0
M  END

     RDKit          3D

 68 72  0  0  0  0  0  0  0  0999 V2000
    2.1389    5.3383    0.2028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0221    4.1543    1.0835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7935    4.0213    2.0720 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479    3.2166    0.7813 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8929    2.0514    1.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2136    1.2680    1.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0103    0.0368    0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1087   -0.7127    0.9957 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1201   -1.1529    0.1257 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7301   -0.0901   -0.4693 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0102   -0.3340   -0.9333 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0310   -1.2961   -2.1045 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2996   -0.7882   -3.1615 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9739   -0.7415    0.1370 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9378    0.2321    0.3894 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2088   -1.1004    1.3823 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0129   -1.7164    2.3326 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0663   -2.0015    0.9690 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4396   -2.4110    2.1624 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9781   -0.5504   -0.3432 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9255   -1.9321   -0.2606 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3090    0.0419   -0.2039 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5074    0.6915    1.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5626    1.8857    0.9155 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7502    2.2359   -0.4132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5136    1.2888   -1.0451 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1330    1.0654   -2.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8644    1.4880   -0.9535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5118    0.2548   -0.8964 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5661    0.3688    0.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2523    1.4258    0.1822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8212   -0.6560    1.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2900   -1.9122    0.7204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8602   -1.8719    0.2985 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5296   -3.2468   -0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4778   -0.7813   -0.6163 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1470    5.7569    0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8571    5.0636   -0.8311 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4244    6.1081    0.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8523    1.5391    1.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827    2.4152    2.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7210   -1.8219   -0.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3837    0.6470   -1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7748   -2.3203   -1.8375 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1047   -1.3219   -2.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7504    0.0597   -3.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5299   -1.6573   -0.1759 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8121   -0.1496    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7434   -0.1642    1.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041   -1.6539    3.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3868   -2.9135    0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7236   -3.0535    2.0076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5848   -0.2970   -1.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8470   -2.3689   -1.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4986    1.1164    1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1409    0.0640    1.9832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7309    2.6918    1.6254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0414    0.0157   -2.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2373    1.6808   -2.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9500    1.4968   -3.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0191    0.1216   -1.8767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8761   -2.3273   -0.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3815   -2.6410    1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2470   -1.7891    1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4398   -3.8774   -0.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8344   -3.8146    0.3472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1447   -3.1354   -1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2025   -1.2401   -1.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
 35 34  1  0
 34 33  1  0
 33 32  1  0
 32 30  1  0
 30 31  2  0
 30 29  1  0
 29 28  1  0
 28 26  1  0
 26 27  1  6
 26 25  1  0
 25 24  1  0
 24 23  1  0
 22 23  1  1
 22 36  1  0
 22 20  1  0
 20 21  1  0
 20  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 36 34  1  0
 18  9  1  0
 36 29  1  0
 22 26  1  0
  6 24  1  0
 35 65  1  0
 35 66  1  0
 35 67  1  0
 34 64  1  1
 33 62  1  0
 33 63  1  0
 29 61  1  6
 27 58  1  0
 27 59  1  0
 27 60  1  0
 24 57  1  1
 23 55  1  0
 23 56  1  0
 36 68  1  6
 20 53  1  6
 21 54  1  0
  9 42  1  6
 11 43  1  6
 12 44  1  0
 12 45  1  0
 13 46  1  0
 14 47  1  6
 15 48  1  0
 16 49  1  1
 17 50  1  0
 18 51  1  6
 19 52  1  0
  5 40  1  0
  5 41  1  0
  1 37  1  0
  1 38  1  0
  1 39  1  0
M  END


  Mrv1652309072223222D          

 36 40  0  0  1  0            999 V2000
   -2.7793    0.9266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1884    0.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3943    0.5749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3914   -0.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8005   -1.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0064   -0.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4031   -1.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -2.2260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3887   -2.4588    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9860   -1.8898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7775   -2.1226    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3749   -1.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1663   -1.7864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9716   -2.9245    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7631   -3.1573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3743   -3.4935    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5684   -4.2953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5828   -3.2607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9854   -3.8297    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022   -1.1510    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0178   -1.7003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5866   -0.2993    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1589   -0.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8144    0.0627    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3002    0.7890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5665    0.5669    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5575    1.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3863    0.7961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8801    0.1239    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7011    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1819    0.7132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0414   -0.7088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5606   -1.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7396   -1.2982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2589   -1.9686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3994   -0.5466    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  6  0  0  0
  7 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 24 23  1  6  0  0  0
  6 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  1  0  0  0
 26 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
 36 29  1  6  0  0  0
 22 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256520

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1COC(=O)[C@H]2O[C@@]3(C)O[C@H]4C[C@]3([C@@H]12)[C@H](O)C(O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C4COC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O13/c1-8-6-32-20(30)18-13(8)23-4-11(35-22(23,3)36-18)10(7-31-9(2)25)17(19(23)29)34-21-16(28)15(27)14(26)12(5-24)33-21/h8,11-16,18-19,21,24,26-29H,4-7H2,1-3H3/t8-,11+,12-,13+,14-,15+,16-,18+,19-,21-,22-,23+/m1/s1

> <INCHI_KEY>
PDSOUSYYTLHECG-AYJSDROWSA-N

> <FORMULA>
C23H32O13

> <MOLECULAR_WEIGHT>
516.496

> <EXACT_MASS>
516.18429109

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.839423900465775

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2R,3S,7S,9R,11S,14S)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0^{1,9}.0^{2,7}]pentadec-12-en-12-yl]methyl acetate

> <JCHEM_LOGP>
-2.9548130159999992

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.960061625228505

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.163731432091902

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810921617898405

> <JCHEM_POLAR_SURFACE_AREA>
190.67

> <JCHEM_REFRACTIVITY>
115.2836

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,3S,7S,9R,11S,14S)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0^{1,9}.0^{2,7}]pentadec-12-en-12-yl]methyl acetate

> <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      -5.188   1.730   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.085   0.655   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.603   1.073   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -4.464  -0.838   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -3.361  -1.912   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.879  -1.494   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.752  -2.658   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.115  -4.155   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.592  -4.590   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.707  -3.528   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -5.185  -3.962   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.300  -2.900   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -7.777  -3.335   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.547  -5.459   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -7.024  -5.894   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.432  -6.521   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.794  -8.018   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.955  -6.087   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.839  -7.149   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.751  -2.149   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.900  -3.174   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.095  -0.559   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.297  -0.287   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.520   0.117   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.560   1.473   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.058   1.058   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.041   2.598   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.588   1.486   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.510   0.231   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.042   0.080   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.939   1.331   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       5.677  -1.323   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.780  -2.575   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.247  -2.423   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.350  -3.675   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.612  -1.020   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18                                                            
CONECT   20    7   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   26   36                                             
CONECT   23   22   24                                                       
CONECT   24   23    6   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   22   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   29   22                                                  
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₃₂O₁₃

Average Mass

516.4960 Da

Monoisotopic Mass

516.18429 Da

IUPAC Name

[(1S,2R,3S,7S,9R,11S,14S)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0^{1,9}.0^{2,7}]pentadec-12-en-12-yl]methyl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1COC(=O)[C@H]2O[C@@]3(C)O[C@H]4C[C@]3([C@@H]12)[C@H](O)C(O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C4COC(C)=O

InChI Identifier

InChI=1S/C23H32O13/c1-8-6-32-20(30)18-13(8)23-4-11(35-22(23,3)36-18)10(7-31-9(2)25)17(19(23)29)34-21-16(28)15(27)14(26)12(5-24)33-21/h8,11-16,18-19,21,24,26-29H,4-7H2,1-3H3/t8-,11+,12-,13+,14-,15+,16-,18+,19-,21-,22-,23+/m1/s1

InChI Key

PDSOUSYYTLHECG-AYJSDROWSA-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
Boletus coniferarum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Furopyran
Furofuran
Ketal
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Pyran
Tetrahydrofuran
Furan
Secondary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Carbonyl group
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	-3	ChemAxon
pKa (Strongest Acidic)	12.16	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	190.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	115.28 m³·mol⁻¹	ChemAxon
Polarizability	49.84 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

9093572

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10918320

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,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate (NP0256520)

MOL for NP0256520 ([(1s,2r,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate)

3D MOL for NP0256520 ([(1s,2r,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate)

3D SDF for NP0256520 ([(1s,2r,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate)

3D-SDF for NP0256520 ([(1s,2r,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate)

PDB for NP0256520 ([(1s,2r,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate)

3D PDB for NP0256520 ([(1s,2r,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate)

SMILES for NP0256520 ([(1s,2r,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate)

INCHI for NP0256520 ([(1s,2r,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate)

Structure for NP0256520 ([(1s,2r,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate)

3D Structure for NP0256520 ([(1s,2r,3s,7s,9r,11s,14s)-14-hydroxy-3,9-dimethyl-6-oxo-13-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,8,10-trioxatetracyclo[9.3.1.0¹,⁹.0²,⁷]pentadec-12-en-12-yl]methyl acetate)