NP-MRD: Showing NP-Card for 2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0221306)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 22:50:59 UTC

Updated at

2022-09-05 22:50:59 UTC

NP-MRD ID

NP0221306

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

2-{[3,5-Dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Astragalus caspicus. 2-{[3,5-Dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]Octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004201504362D          

 64 72  0  0  0  0            999 V2000
    4.4417    5.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9735    4.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3428    4.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042    5.2544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5053    4.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282    4.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6390    3.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032    2.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3076    3.2909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  0  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
    6.5072    1.1313    0.0000 O   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  0  0  0  0  0  0  0  0  0  0
    4.1995    0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  0  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  0  0  0  0  0  0  0  0  0  0
    2.2123   -0.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441   -1.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5562   -0.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0880   -1.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8077   -2.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3396   -2.9102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9956   -2.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153   -3.2006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638   -1.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6517   -1.9392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352    0.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   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
    2.2411    1.7952    0.0000 C   0  0  0  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  0  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  0  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
   -0.1953    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2877    0.4384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5680   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0362   -0.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3165   -1.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3077   -1.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274   -2.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7847   -2.3748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650   -3.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8771   -3.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4089   -2.6653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5332   -3.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135   -4.5574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2790   -3.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8108   -4.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5593   -2.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714   -2.7151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0562   -0.0471    0.0000 C   0  0  0  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  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  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 17 39  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 11 42  1  0  0  0  0
 15 42  1  0  0  0  0
 42 43  1  0  0  0  0
 34 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 54 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  1  0  0  0  0
 59 60  1  0  0  0  0
 59 61  1  0  0  0  0
 52 61  1  0  0  0  0
 61 62  1  0  0  0  0
 50 63  1  0  0  0  0
 45 63  1  0  0  0  0
 63 64  1  0  0  0  0
M  END


  Mrv1533004201504362D          

 64 72  0  0  0  0            999 V2000
    4.4417    5.3533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9735    4.7226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3428    4.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042    5.2544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5053    4.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282    4.1514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6390    3.3872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    2.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032    2.2837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3076    3.2909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5020    2.2041    0.0000 C   0  0  0  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
    6.5072    1.1313    0.0000 O   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  0  0  0  0  0  0  0  0  0  0
    4.1995    0.6540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850    1.3097    0.0000 C   0  0  0  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  0  0  0  0  0  0  0  0  0  0
    2.2123   -0.3873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7441   -1.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5562   -0.8728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0880   -1.5035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8077   -2.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3396   -2.9102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9956   -2.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153   -3.2006    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4638   -1.7940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6517   -1.9392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608    1.0193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1486    0.8741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4352    0.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.5048    0.0000 C   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
    2.2411    1.7952    0.0000 C   0  0  0  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  0  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  0  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
   -0.1953    1.3596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4756    0.5836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2877    0.4384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5680   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0362   -0.9682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3165   -1.7441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2241   -0.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3077   -1.4537    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274   -2.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7847   -2.3748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0650   -3.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8771   -3.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4089   -2.6653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5332   -3.7815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135   -4.5574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2790   -3.6362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8108   -4.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5593   -2.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714   -2.7151    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0562   -0.0471    0.0000 C   0  0  0  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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  5 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  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  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 19 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 17 39  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 11 42  1  0  0  0  0
 15 42  1  0  0  0  0
 42 43  1  0  0  0  0
 34 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 54 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  1  0  0  0  0
 59 60  1  0  0  0  0
 59 61  1  0  0  0  0
 52 61  1  0  0  0  0
 61 62  1  0  0  0  0
 50 63  1  0  0  0  0
 45 63  1  0  0  0  0
 63 64  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221306

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)C1CCC(C)(O1)C1C(O)CC2(C)C3CC(OC4OCC(O)C(O)C4O)C4C5(CC35CCC12C)CCC(OC1OCC(O)C(OC2OC(CO)C(O)C(O)C2O)C1O)C4(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C46H76O18/c1-40(2)26(62-38-33(56)34(22(50)18-59-38)63-39-32(55)30(53)29(52)24(16-47)61-39)9-11-46-19-45(46)13-12-42(5)35(44(7)10-8-27(64-44)41(3,4)57)20(48)15-43(42,6)25(45)14-23(36(40)46)60-37-31(54)28(51)21(49)17-58-37/h20-39,47-57H,8-19H2,1-7H3

> <INCHI_KEY>
IWHNYAWBUJCOCJ-UHFFFAOYSA-N

> <FORMULA>
C46H76O18

> <MOLECULAR_WEIGHT>
917.096

> <EXACT_MASS>
916.503165607

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
140

> <JCHEM_AVERAGE_POLARIZABILITY>
97.66138111752585

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.21

> <JCHEM_LOGP>
-1.4520437339999979

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.222997027918074

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.778425901982262

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5265806214224815

> <JCHEM_POLAR_SURFACE_AREA>
287.13999999999993

> <JCHEM_REFRACTIVITY>
221.03090000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       8.291   9.993   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.284   8.815   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.107   7.823   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.461   9.808   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.277   7.638   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.813   7.749   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.393   6.323   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      12.326   4.263   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.908   6.143   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  O   UNK     0      12.147   2.112   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.839   1.221   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.130  -0.723   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.122  -1.900   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.638  -1.629   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.631  -2.807   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.108  -4.255   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.101  -5.432   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.592  -4.526   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.069  -5.974   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.599  -3.349   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.083  -3.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.674   0.186   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.812   0.858   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -0.888   1.089   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -2.404   0.818   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -2.927  -0.630   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -1.934  -1.807   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -2.457  -3.256   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -0.418  -1.536   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       0.574  -2.714   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       0.051  -4.162   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -1.465  -4.433   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -1.988  -5.881   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -3.504  -6.152   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -4.497  -4.975   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -0.995  -7.059   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      -1.518  -8.507   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0       0.521  -6.788   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       1.513  -7.965   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0       1.044  -5.339   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0       2.560  -5.068   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0       0.105  -0.088   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       1.621   0.183   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8    5                                                       
CONECT   11    8   12   42                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   42                                             
CONECT   16   15                                                            
CONECT   17   15   18   39                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   30                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21   29                                                  
CONECT   29   28                                                            
CONECT   30   19   31   37                                                  
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35   44                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   30   38   39                                             
CONECT   38   37   39                                                       
CONECT   39   38   17   37   40                                             
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   11   15   43                                             
CONECT   43   42                                                            
CONECT   44   34   45                                                       
CONECT   45   44   46   63                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   63                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   61                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55   57                                                  
CONECT   55   54   56                                                       
CONECT   56   55                                                            
CONECT   57   54   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60   61                                                  
CONECT   60   59                                                            
CONECT   61   59   52   62                                                  
CONECT   62   61                                                            
CONECT   63   50   45   64                                                  
CONECT   64   63                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  144    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₆H₇₆O₁₈

Average Mass

917.0960 Da

Monoisotopic Mass

916.50317 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(C)(O)C1CCC(C)(O1)C1C(O)CC2(C)C3CC(OC4OCC(O)C(O)C4O)C4C5(CC35CCC12C)CCC(OC1OCC(O)C(OC2OC(CO)C(O)C(O)C2O)C1O)C4(C)C

InChI Identifier

InChI=1S/C46H76O18/c1-40(2)26(62-38-33(56)34(22(50)18-59-38)63-39-32(55)30(53)29(52)24(16-47)61-39)9-11-46-19-45(46)13-12-42(5)35(44(7)10-8-27(64-44)41(3,4)57)20(48)15-43(42,6)25(45)14-23(36(40)46)60-37-31(54)28(51)21(49)17-58-37/h20-39,47-57H,8-19H2,1-7H3

InChI Key

IWHNYAWBUJCOCJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Astragalus caspicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Triterpene saponin
Triterpene glycoside
Cycloartanol-skeleton
9b,19-cyclo-lanostane-skeleton
Cycloartane-skeleton
Triterpenoid
16-hydroxysteroid
Hydroxysteroid
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Acetal
Dialkyl ether
Polyol
Ether
Alcohol
Organic oxygen compound
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.21	ALOGPS
logP	-1.5	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	11.78	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	287.14 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	221.03 m³·mol⁻¹	ChemAxon
Polarizability	97.66 Å³	ChemAxon
Number of Rings	9	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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0221306)

MOL for NP0221306 (2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0221306 (2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0221306 (2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0221306 (2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0221306 (2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0221306 (2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0221306 (2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0221306 (2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0221306 (2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0221306 (2-{[3,5-dihydroxy-2-({14-hydroxy-15-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-7,7,12,16-tetramethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl}oxy)oxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)