NP-MRD: Showing NP-Card for 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate (NP0194572)

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Record Information

Version

2.0

Created at

2022-09-04 12:15:10 UTC

Updated at

2022-09-04 12:15:11 UTC

NP-MRD ID

NP0194572

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

Description

3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,8aS,12aR,12bR,14bR)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate is found in Agrimonia eupatoria, Diospyros kaki, Rubus coreanus and Sargentodoxa cuneata. Based on a literature review very few articles have been published on 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,8aS,12aR,12bR,14bR)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042214152D          

 46 51  0  0  1  0            999 V2000
    4.1763   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638    1.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763    2.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638    2.9388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388    1.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263    2.2243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263    0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9750   -0.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3638   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2205   -0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1390   -1.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4138   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1134   -3.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426   -3.6015    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
  3  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
  6  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
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 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
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 32 41  1  0  0  0  0
 27 41  1  0  0  0  0
 41 42  1  1  0  0  0
 43 24  1  1  0  0  0
  5 43  1  0  0  0  0
 43 44  1  0  0  0  0
  2 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  6  0  0  0
M  END


  Mrv1652309042214152D          

 46 51  0  0  1  0            999 V2000
    4.1763   -3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4138    0.0809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638    1.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1763    2.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7638    2.9388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388    1.5099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263    2.2243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263    0.7954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7013    0.7954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9388    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6513   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.8888   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9750   -0.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3013   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -0.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -1.3480    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3638   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2205   -0.5356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1390   -1.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3638   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7763   -3.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5388   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1263   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.7138   -2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4138   -2.7770    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1134   -3.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426   -3.6015    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
  3  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
  6  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
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 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
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 27 26  1  1  0  0  0
 27 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 32 41  1  0  0  0  0
 27 41  1  0  0  0  0
 41 42  1  1  0  0  0
 43 24  1  1  0  0  0
  5 43  1  0  0  0  0
 43 44  1  0  0  0  0
  2 44  1  0  0  0  0
 44 45  1  1  0  0  0
 44 46  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0194572

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(CCC3(C)C(=CC[C@@H]4[C@@]5(C)CC(O)C(O)C(C)(C)[C@H]5CCC34C)[C@H]2[C@]1(C)O)C(=O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C36H58O10/c1-18-10-13-36(30(43)46-29-26(41)25(40)24(39)21(17-37)45-29)15-14-33(5)19(27(36)35(18,7)44)8-9-23-32(4)16-20(38)28(42)31(2,3)22(32)11-12-34(23,33)6/h8,18,20-29,37-42,44H,9-17H2,1-7H3/t18?,20?,21?,22-,23-,24?,25?,26?,27+,28?,29?,32+,33?,34?,35-,36?/m1/s1

> <INCHI_KEY>
MLKQAGPAYHTNQQ-KAXWTKPKSA-N

> <FORMULA>
C36H58O10

> <MOLECULAR_WEIGHT>
650.85

> <EXACT_MASS>
650.402998068

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
104

> <JCHEM_AVERAGE_POLARIZABILITY>
71.04480115477782

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,8aS,12aR,12bR,14bR)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

> <JCHEM_LOGP>
2.001580214333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.058478901625712

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.178050822229903

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810936801758814

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
169.0958

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,8aS,12aR,12bR,14bR)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       7.796  -6.517   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.566  -5.184   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.796  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.566  -2.516   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.106  -2.516   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -1.183   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.106   0.151   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.796  -1.183   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.026   0.151   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.796   1.485   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.026   2.818   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.796   4.152   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.026   5.486   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.486   2.818   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.716   4.152   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.716   1.485   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.176   1.485   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.486   0.151   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.716  -1.183   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.876  -1.183   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.416  -1.183   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.186  -2.516   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.956  -1.183   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.416  -3.850   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.186  -5.184   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      14.726  -5.184   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.496  -3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.726  -2.516   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.887  -0.985   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.496  -1.183   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.036  -1.183   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      17.806  -2.516   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      19.346  -2.516   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.078  -1.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      20.793  -1.990   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      20.116  -3.850   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      21.656  -3.850   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      19.346  -5.184   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      20.116  -6.517   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      17.806  -5.184   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      17.036  -3.850   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      16.266  -5.184   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      10.876  -3.850   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      10.106  -5.184   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      11.412  -6.000   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      10.159  -6.723   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   44                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   20   43                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    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    5   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   28                                             
CONECT   23   22                                                            
CONECT   24   22   25   43                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   41                                                  
CONECT   28   27   22   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   41                                                  
CONECT   33   32   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   32   27   42                                             
CONECT   42   41                                                            
CONECT   43   24    5   44                                                  
CONECT   44   43    2   45   46                                             
CONECT   45   44                                                            
CONECT   46   44                                                            
MASTER        0    0    0    0    0    0    0    0   46    0  102    0
END

View in JSmol

Synonyms

Value	Source
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,8as,12ar,12BR,14BR)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid	Generator

Chemical Formula

C₃₆H₅₈O₁₀

Average Mass

650.8500 Da

Monoisotopic Mass

650.40300 Da

IUPAC Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,8aS,12aR,12bR,14bR)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Traditional Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,8aS,12aR,12bR,14bR)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

CAS Registry Number

Not Available

SMILES

CC1CCC2(CCC3(C)C(=CC[C@@H]4[C@@]5(C)CC(O)C(O)C(C)(C)[C@H]5CCC34C)[C@H]2[C@]1(C)O)C(=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C36H58O10/c1-18-10-13-36(30(43)46-29-26(41)25(40)24(39)21(17-37)45-29)15-14-33(5)19(27(36)35(18,7)44)8-9-23-32(4)16-20(38)28(42)31(2,3)22(32)11-12-34(23,33)6/h8,18,20-29,37-42,44H,9-17H2,1-7H3/t18?,20?,21?,22-,23-,24?,25?,26?,27+,28?,29?,32+,33?,34?,35-,36?/m1/s1

InChI Key

MLKQAGPAYHTNQQ-KAXWTKPKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agrimonia eupatoria	LOTUS Database	35616633
Diospyros kaki	LOTUS Database	35616633
Rubus coreanus	LOTUS Database	35616633
Sargentodoxa cuneata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Hexose monosaccharide
Oxane
Monosaccharide
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2	ChemAxon
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	169.1 m³·mol⁻¹	ChemAxon
Polarizability	71.04 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

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

137705657

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate (NP0194572)

MOL for NP0194572 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D MOL for NP0194572 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D SDF for NP0194572 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D-SDF for NP0194572 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

PDB for NP0194572 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D PDB for NP0194572 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

SMILES for NP0194572 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

INCHI for NP0194572 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

Structure for NP0194572 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)

3D Structure for NP0194572 (3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,8as,12ar,12br,14br)-1,10,11-trihydroxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate)