NP-MRD: Showing NP-Card for (2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol (NP0219984)

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Record Information

Version

2.0

Created at

2022-09-05 21:10:10 UTC

Updated at

2022-09-05 21:10:10 UTC

NP-MRD ID

NP0219984

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(2R,3R,4S,5S,6R)-2-[(2S)-4-[(1S,2S,4S,6R,7S,8R,9S,12S,13R,14R,16R)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. (2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol is found in Nolina microcarpa. Based on a literature review very few articles have been published on (2R,3R,4S,5S,6R)-2-[(2S)-4-[(1S,2S,4S,6R,7S,8R,9S,12S,13R,14R,16R)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052223102D          

 44 49  0  0  1  0            999 V2000
    3.1293   -1.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339   -2.1386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8507   -2.5471    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3696   -3.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5486   -3.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0675   -3.8058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4073   -4.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2465   -3.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7654   -4.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0556   -4.3127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5367   -4.9829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3577   -4.9013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8389   -5.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598   -5.4898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6975   -4.1495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5185   -4.0679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2163   -3.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5562   -2.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3954   -3.5610    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0858   -2.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1820   -1.7915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030   -1.8731    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7151   -1.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3313   -2.0052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1513   -1.9143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4826   -1.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3026   -1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7913   -1.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6112   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0999   -2.3064    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9199   -2.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7686   -3.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9486   -3.1529    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6173   -3.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4600   -2.4882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1286   -3.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6400   -2.5790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3087   -3.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4887   -3.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -2.7607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5915   -3.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1791   -2.6791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4669   -3.0956    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3853   -3.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  3 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 25 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 24 40  1  0  0  0  0
 40 41  1  1  0  0  0
 42 40  1  1  0  0  0
 22 42  1  0  0  0  0
 42 43  1  0  0  0  0
  3 43  1  0  0  0  0
 43 44  1  6  0  0  0
M  END


  Mrv1652309052223102D          

 44 49  0  0  1  0            999 V2000
    3.1293   -1.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339   -2.1386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8507   -2.5471    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3696   -3.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5486   -3.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0675   -3.8058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4073   -4.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2465   -3.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7654   -4.3943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0556   -4.3127    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5367   -4.9829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3577   -4.9013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8389   -5.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6598   -5.4898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6975   -4.1495    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5185   -4.0679    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2163   -3.4793    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5562   -2.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3954   -3.5610    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0858   -2.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1820   -1.7915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0030   -1.8731    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7151   -1.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3313   -2.0052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1513   -1.9143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.4826   -1.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3026   -1.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7913   -1.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6112   -1.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0999   -2.3064    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9199   -2.2156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7686   -3.0620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9486   -3.1529    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6173   -3.9084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4600   -2.4882    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1286   -3.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6400   -2.5790    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3087   -3.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4887   -3.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -2.7607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5915   -3.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1791   -2.6791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4669   -3.0956    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3853   -3.9166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  1  0  0  0
  3 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 28 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 25 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 24 40  1  0  0  0  0
 40 41  1  1  0  0  0
 42 40  1  1  0  0  0
 22 42  1  0  0  0  0
 42 43  1  0  0  0  0
  3 43  1  0  0  0  0
 43 44  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0219984

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@]1(CC[C@H](C)CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O[C@H]2C[C@H]3[C@@H]4CC=C5C[C@@H](O)C[C@@H](O)[C@]5(C)[C@H]4CC[C@]3(C)[C@H]2[C@@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C34H56O10/c1-17(16-42-31-30(40)29(39)28(38)25(15-35)43-31)8-11-34(41-5)18(2)27-24(44-34)14-23-21-7-6-19-12-20(36)13-26(37)33(19,4)22(21)9-10-32(23,27)3/h6,17-18,20-31,35-40H,7-16H2,1-5H3/t17-,18-,20+,21+,22-,23-,24-,25+,26+,27-,28+,29-,30+,31+,32-,33-,34+/m0/s1

> <INCHI_KEY>
GHOACOKPHWTSLQ-CAYKSLNOSA-N

> <FORMULA>
C34H56O10

> <MOLECULAR_WEIGHT>
624.812

> <EXACT_MASS>
624.387348003

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
70.6283057774203

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-[(2S)-4-[(1S,2S,4S,6R,7S,8R,9S,12S,13R,14R,16R)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
1.3342876666666657

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.178930518333399

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.208473237872111

> <JCHEM_PKA_STRONGEST_BASIC>
-2.750183527683701

> <JCHEM_POLAR_SURFACE_AREA>
158.3

> <JCHEM_REFRACTIVITY>
162.41240000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-[(2S)-4-[(1S,2S,4S,6R,7S,8R,9S,12S,13R,14R,16R)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       5.841  -2.452   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.850  -3.992   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.188  -4.755   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.290  -6.006   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.757  -5.853   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.859  -7.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.494  -8.507   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.327  -6.952   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.429  -8.203   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.104  -8.050   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.002  -9.301   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.534  -9.149   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.433 -10.400   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.965 -10.248   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.169  -7.746   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.701  -7.593   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.271  -6.495   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.905  -5.091   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.738  -6.647   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.160  -5.396   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       7.806  -3.344   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.339  -3.497   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.668  -2.719   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.818  -3.743   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.349  -3.573   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.968  -2.163   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.498  -1.993   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.410  -3.234   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      17.941  -3.065   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      18.853  -4.305   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      20.384  -4.136   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      18.235  -5.716   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.704  -5.885   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      16.086  -7.296   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      15.792  -4.645   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      15.173  -6.055   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.261  -4.814   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.643  -6.225   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.112  -6.394   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.200  -5.153   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.438  -6.491   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       9.668  -5.001   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.338  -5.779   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.186  -7.311   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21   43                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    3   22                                                       
CONECT   22   21   23   42                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   40                                                  
CONECT   25   24   26   37                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   28   36   37                                             
CONECT   36   35                                                            
CONECT   37   35   25   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   24   41   42                                             
CONECT   41   40                                                            
CONECT   42   40   22   43                                                  
CONECT   43   42    3   44                                                  
CONECT   44   43                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₅₆O₁₀

Average Mass

624.8120 Da

Monoisotopic Mass

624.38735 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-[(2S)-4-[(1S,2S,4S,6R,7S,8R,9S,12S,13R,14R,16R)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@]1(CC[C@H](C)CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O[C@H]2C[C@H]3[C@@H]4CC=C5C[C@@H](O)C[C@@H](O)[C@]5(C)[C@H]4CC[C@]3(C)[C@H]2[C@@H]1C

InChI Identifier

InChI=1S/C34H56O10/c1-17(16-42-31-30(40)29(39)28(38)25(15-35)43-31)8-11-34(41-5)18(2)27-24(44-34)14-23-21-7-6-19-12-20(36)13-26(37)33(19,4)22(21)9-10-32(23,27)3/h6,17-18,20-31,35-40H,7-16H2,1-5H3/t17-,18-,20+,21+,22-,23-,24-,25+,26+,27-,28+,29-,30+,31+,32-,33-,34+/m0/s1

InChI Key

GHOACOKPHWTSLQ-CAYKSLNOSA-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
Nolina microcarpa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal saponins

Alternative Parents

Substituents

Steroidal saponin
Furostane-skeleton
3-hydroxy-delta-5-steroid
3-hydroxysteroid
1-hydroxysteroid
Hydroxysteroid
3-beta-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
Delta-5-steroid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Ketal
Monosaccharide
Fatty acyl
Oxane
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Primary 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	1.33	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	158.3 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	162.41 m³·mol⁻¹	ChemAxon
Polarizability	70.63 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	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

163093610

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol (NP0219984)

MOL for NP0219984 ((2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0219984 ((2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0219984 ((2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0219984 ((2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0219984 ((2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0219984 ((2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0219984 ((2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0219984 ((2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0219984 ((2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0219984 ((2r,3r,4s,5s,6r)-2-[(2s)-4-[(1s,2s,4s,6r,7s,8r,9s,12s,13r,14r,16r)-14,16-dihydroxy-6-methoxy-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icos-18-en-6-yl]-2-methylbutoxy]-6-(hydroxymethyl)oxane-3,4,5-triol)