NP-MRD: Showing NP-Card for 5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate (NP0154738)

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Record Information

Version

2.0

Created at

2022-09-02 11:41:23 UTC

Updated at

2022-09-02 11:41:24 UTC

NP-MRD ID

NP0154738

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate

Description

5-(Acetyloxy)-4-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl}oxy)oxan-3-yl acetate 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. 5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate is found in Astragalus sieversianus. 5-(Acetyloxy)-4-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl}oxy)oxan-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171508222D          

 60 66  0  0  0  0            999 V2000
   10.7345   -2.3054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2026   -1.6747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4829   -0.8988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905   -1.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8587   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0466   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0743   -0.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607    0.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7603   -1.2284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4648   -0.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2627   -0.6103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1175   -1.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6997   -1.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6892   -2.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608   -2.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0943   -2.5889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2840   -1.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557    2.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3239    3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117    2.9353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799    3.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2602    4.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284    4.9727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0723    4.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526    5.2631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041    3.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4163    4.0017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8025    2.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5311    1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8875    0.9934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5435    1.4789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6360    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1390   -0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9511   -0.2681    0.0000 O   0  0  0  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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 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
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 18 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 31 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
 16 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 49  1  0  0  0  0
 42 49  1  0  0  0  0
 49 50  1  0  0  0  0
 15 51  1  0  0  0  0
 10 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
  8 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 56 58  1  0  0  0  0
 54 59  1  0  0  0  0
  5 59  1  0  0  0  0
 59 60  1  0  0  0  0
M  END

     RDKit          3D

134140  0  0  0  0  0  0  0  0999 V2000
   -8.3803    1.6004    3.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5923    0.8886    2.8458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1976   -0.3004    2.9973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2659    1.5182    1.6758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4964    0.8849    0.6241 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.2791    1.6441    0.3346 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1591    1.0502   -0.1362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9817    1.3321    0.5056 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0377    2.2186   -0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528    1.7039   -0.4406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549    0.2349   -0.8442 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4184    0.1977   -2.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894   -0.6143    0.1448 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5053   -1.5772    0.8568 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0461   -2.3314    1.8535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8733   -3.6826    1.7154 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2356   -4.2906    2.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5124   -6.3395    0.2285 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7829    1.9068   -0.3677 C   0  0  2  0  0  0  0  0  0  0  0  0
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   10.1259    1.4357   -1.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0310    0.0345    0.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3669   -0.0337   -1.6895 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5149    0.8494   -0.6022 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -7.4473    0.6905   -0.5224 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.2661   -0.5571   -1.1344 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0400    2.2944    1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004171508222D          

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M  END
> <DATABASE_ID>
NP0154738

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1COC(OC2CCC3(C)C(C(CC4C5(C)CC(O)C(C6(C)CCC(O6)C(C)(C)O)C5(C)CCC34C)OC3OCC(O)C(O)C3O)C2(C)C)C(OC(C)=O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C45H74O15/c1-22(46)56-27-21-55-38(34(32(27)51)57-23(2)47)59-29-12-14-42(8)36(39(29,3)4)26(58-37-33(52)31(50)25(49)20-54-37)18-28-41(42,7)16-17-43(9)35(24(48)19-44(28,43)10)45(11)15-13-30(60-45)40(5,6)53/h24-38,48-53H,12-21H2,1-11H3

> <INCHI_KEY>
ZZBMDTNGBMRRFC-UHFFFAOYSA-N

> <FORMULA>
C45H74O15

> <MOLECULAR_WEIGHT>
855.072

> <EXACT_MASS>
854.502771683

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
134

> <JCHEM_AVERAGE_POLARIZABILITY>
93.89308487994006

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(acetyloxy)-4-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxy)oxan-3-yl acetate

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
2.109337300000001

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.871856816118974

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.16133088649843

> <JCHEM_PKA_STRONGEST_BASIC>
-2.875943152661687

> <JCHEM_POLAR_SURFACE_AREA>
220.12999999999997

> <JCHEM_REFRACTIVITY>
213.32380000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.43e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(acetyloxy)-4-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxy)oxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      20.038  -4.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.045  -3.126   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      19.568  -1.678   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.028  -1.314   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.605  -1.308   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.047   1.738   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.355   2.629   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.286  -2.293   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.868  -0.413   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.490  -1.139   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.219  -2.655   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.306  -2.866   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.286  -3.766   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.354  -4.876   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.176  -4.833   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -2.397  -2.698   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       9.064   4.573   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       8.071   5.750   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       6.555   5.479   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       5.563   6.657   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.086   8.105   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       5.093   9.282   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       7.602   8.376   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       8.125   9.824   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       8.594   7.199   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      10.110   7.470   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      10.831   3.743   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      12.191   3.252   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      16.067   0.406   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      16.590   1.854   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      15.597   3.032   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      14.081   2.761   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      16.120   4.480   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      18.575  -0.500   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   59                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   54                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   51                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   19                                             
CONECT   14   13                                                            
CONECT   15   13   16   51                                                  
CONECT   16   15   17   41                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   29                                                  
CONECT   19   18   13   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   29                                             
CONECT   24   23                                                            
CONECT   25   23   26   31                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   18   23   30                                             
CONECT   30   29                                                            
CONECT   31   25   32   33   36                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35   31                                                       
CONECT   37   35   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37                                                            
CONECT   41   16   42                                                       
CONECT   42   41   43   49                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   42   50                                                  
CONECT   50   49                                                            
CONECT   51   15   10   52   53                                             
CONECT   52   51                                                            
CONECT   53   51                                                            
CONECT   54    8   55   59                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56                                                            
CONECT   59   54    5   60                                                  
CONECT   60   59                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  132    0
END

View in JSmol

Synonyms

Value	Source
5-(Acetyloxy)-4-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0,.0,]heptadecan-5-yl}oxy)oxan-3-yl acetic acid	Generator
5-(Acetyloxy)-4-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxy)oxan-3-yl acetic acid	Generator

Chemical Formula

C₄₅H₇₄O₁₅

Average Mass

855.0720 Da

Monoisotopic Mass

854.50277 Da

IUPAC Name

5-(acetyloxy)-4-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-[(3,4,5-trihydroxyoxan-2-yl)oxy]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxy)oxan-3-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)OC1COC(OC2CCC3(C)C(C(CC4C5(C)CC(O)C(C6(C)CCC(O6)C(C)(C)O)C5(C)CCC34C)OC3OCC(O)C(O)C3O)C2(C)C)C(OC(C)=O)C1O

InChI Identifier

InChI=1S/C45H74O15/c1-22(46)56-27-21-55-38(34(32(27)51)57-23(2)47)59-29-12-14-42(8)36(39(29,3)4)26(58-37-33(52)31(50)25(49)20-54-37)18-28-41(42,7)16-17-43(9)35(24(48)19-44(28,43)10)45(11)15-13-30(60-45)40(5,6)53/h24-38,48-53H,12-21H2,1-11H3

InChI Key

ZZBMDTNGBMRRFC-UHFFFAOYSA-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
Astragalus sieversianus	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
Triterpenoid
Hydroxysteroid
16-hydroxysteroid
Glycosyl compound
O-glycosyl compound
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Acetal
Carboxylic acid derivative
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	3.11	ALOGPS
logP	2.11	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	12.16	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	220.13 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	213.32 m³·mol⁻¹	ChemAxon
Polarizability	93.89 Å³	ChemAxon
Number of Rings	7	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 5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate (NP0154738)

MOL for NP0154738 (5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

3D MOL for NP0154738 (5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

3D SDF for NP0154738 (5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

3D-SDF for NP0154738 (5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

PDB for NP0154738 (5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

3D PDB for NP0154738 (5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

SMILES for NP0154738 (5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

INCHI for NP0154738 (5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

Structure for NP0154738 (5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

3D Structure for NP0154738 (5-(acetyloxy)-4-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-[(3,4,5-trihydroxyoxan-2-yl)oxy]-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)