NP-MRD: Showing NP-Card for [8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid (NP0254490)

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Record Information

Version

2.0

Created at

2022-09-07 18:39:54 UTC

Updated at

2022-09-07 18:39:54 UTC

NP-MRD ID

NP0254490

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid

Description

{[8A-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14,14a,14b-icosahydropicen-4-yl]methoxy}sulfonic acid 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. [8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid is found in Zygophyllum fabago. {[8A-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14,14a,14b-icosahydropicen-4-yl]methoxy}sulfonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231522152D          

 58 64  0  0  0  0            999 V2000
    1.5395   -3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4895   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3145   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7270   -2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5520   -2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9645   -1.6796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.9645   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9337   -6.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8522   -5.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9955   -6.3466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2520   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6020   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7770   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6907   -6.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -5.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -5.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1105   -3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -3.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -2.3941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8230   -2.3941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -0.9651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9355   -1.6796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.6796    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  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
 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
 14 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
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 14 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 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
 27 28  2  0  0  0  0
 27 29  2  0  0  0  0
 27 30  1  0  0  0  0
 23 31  1  0  0  0  0
  8 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
  7 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  4 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
 39 40  1  0  0  0  0
  3 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 40 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
  2 45  1  0  0  0  0
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 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 50 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
 55 56  1  0  0  0  0
 55 57  1  0  0  0  0
 48 57  1  0  0  0  0
 57 58  1  0  0  0  0
M  END

     RDKit          3D

126132  0  0  0  0  0  0  0  0999 V2000
    3.7212   -2.1677   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6828   -0.9528    0.6591 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1347   -0.4703    0.7183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1473   -1.4468    1.1903 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4330   -1.1255    1.2482 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1452   -0.8278    0.1122 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9591    0.2720    0.3380 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3808    0.7245   -0.9113 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.9326    2.1103   -0.7800 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0079    2.2128    0.0683 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3560   -0.2594   -1.4668 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.6711    0.2495   -1.4815 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4034   -1.5649   -0.7347 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.3293   -1.4921    0.3230 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0891   -2.0317   -0.2099 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4996   -2.8720   -1.1474 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5196    1.7595   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1493    1.4883    0.4971 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3911    1.6877    1.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7082    3.0565    2.1312 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2079    2.4724   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9413    1.9373   -0.6774 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3635    0.8350    0.1578 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -8.6566    1.6959    2.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9600    1.7192    2.0323 C   0  0  2  0  0  0  0  0  0  0  0  0
  -10.9580    1.1107    2.7940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8955    1.0908    0.6539 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.1742    0.8153    0.2366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0445   -0.1869    0.7323 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.9786   -0.7843   -0.5004 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.6248   -2.1348   -0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6037   -0.0742   -1.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1393   -0.7538   -3.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7028   -0.0786   -4.4101 S   0  0  0  0  0  6  0  0  0  0  0  0
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   -0.5467   -0.5011   -1.7858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7869    0.1026    0.0715 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7643   -3.0737    0.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8437   -2.1772   -0.9458 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6143   -2.1803   -0.9061 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4463   -1.2049    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284   -1.8655    2.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0813   -2.3888    0.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5529   -0.7583   -0.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4728    0.7922   -1.5570 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2488    2.4938   -1.7891 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1411    2.7934   -0.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5390    3.0335   -0.1753 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1048   -0.3959   -2.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9901    0.1804   -0.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8130   -2.3239   -1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.0839   -2.1905    0.9558 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2621   -2.6280    0.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0769    3.3019    0.6345 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6915    3.0465   -0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0569    1.7082   -1.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1849    2.7792   -0.6385 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0254490

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C3CCC4C5(C)CCC(OC6OCC(O)C(O)C6O)C(C)(COS(O)(=O)=O)C5CCC4(C)C3(C)CCC2(CO)CC=C1COC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C41H68O16S/c1-21-22(17-53-35-34(49)32(47)31(46)25(16-42)56-35)8-13-41(19-43)15-14-39(4)23(29(21)41)6-7-27-37(2)11-10-28(57-36-33(48)30(45)24(44)18-54-36)38(3,20-55-58(50,51)52)26(37)9-12-40(27,39)5/h8,21,23-36,42-49H,6-7,9-20H2,1-5H3,(H,50,51,52)

> <INCHI_KEY>
RBHJQJQPNRFRHI-UHFFFAOYSA-N

> <FORMULA>
C41H68O16S

> <MOLECULAR_WEIGHT>
849.04

> <EXACT_MASS>
848.422807284

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
126

> <JCHEM_AVERAGE_POLARIZABILITY>
91.15734824501494

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14,14a,14b-icosahydropicen-4-yl]methoxy}sulfonic acid

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
-0.7166925484865507

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.92698902099759

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.4402644670122786

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835523132306

> <JCHEM_POLAR_SURFACE_AREA>
262.35999999999996

> <JCHEM_REFRACTIVITY>
206.16080000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.17e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1H-picen-4-yl]methoxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       2.874  -5.803   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.104  -7.136   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874  -8.470   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414  -8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.184  -7.136   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.724  -7.136   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494  -8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.034  -8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.264  -7.136   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.804  -7.136   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.344  -7.136   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.114  -8.470   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.654  -8.470   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      14.424  -7.136   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.654  -5.803   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.424  -4.469   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.964  -4.469   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      16.734  -3.135   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      16.734  -5.803   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.274  -5.803   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      15.964  -7.136   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.734  -8.470   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.344  -9.804   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.076 -11.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.791 -10.330   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.058 -11.847   0.000  0.00  0.00           O+0
HETATM   27  S   UNK     0      14.505 -12.374   0.000  0.00  0.00           S+0
HETATM   28  O   UNK     0      15.032 -10.927   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      15.952 -12.900   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      13.979 -13.821   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       9.804  -9.804   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.034 -11.137   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.494 -11.137   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.724  -9.804   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.954 -11.137   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.184  -9.804   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.023 -11.335   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.414 -11.137   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.874 -11.137   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.104  -9.804   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.334 -11.137   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -0.206 -11.137   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       0.564  -9.804   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -0.206  -8.470   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.564  -7.136   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -0.206  -5.803   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -1.746  -5.803   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -2.516  -4.469   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -4.056  -4.469   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -4.826  -3.135   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -6.366  -3.135   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -7.136  -4.469   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -4.056  -1.802   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      -4.826  -0.468   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -2.516  -1.802   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -1.746  -0.468   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -1.746  -3.135   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      -0.206  -3.135   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   45                                                  
CONECT    3    2    4   40                                                  
CONECT    4    3    5   36                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   34                                                  
CONECT    8    7    9   10   31                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   14   22                                                  
CONECT   22   21                                                            
CONECT   23   12   24   25   31                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   23    8   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    7   35   36                                             
CONECT   35   34                                                            
CONECT   36   34    4   37   38                                             
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39    3   41   43                                             
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   40   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44    2   46                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   57                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   53                                                  
CONECT   51   50   52                                                       
CONECT   52   51                                                            
CONECT   53   50   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55   48   58                                                  
CONECT   58   57                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  128    0
END

View in JSmol

Synonyms

Value	Source
{[8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14,14a,14b-icosahydropicen-4-yl]methoxy}sulfonate	Generator
{[8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14,14a,14b-icosahydropicen-4-yl]methoxy}sulphonate	Generator
{[8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14,14a,14b-icosahydropicen-4-yl]methoxy}sulphonic acid	Generator

Chemical Formula

C₄₁H₆₈O₁₆S

Average Mass

849.0400 Da

Monoisotopic Mass

848.42281 Da

IUPAC Name

{[8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,12,12a,12b,13,14,14a,14b-icosahydropicen-4-yl]methoxy}sulfonic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1C2C3CCC4C5(C)CCC(OC6OCC(O)C(O)C6O)C(C)(COS(O)(=O)=O)C5CCC4(C)C3(C)CCC2(CO)CC=C1COC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C41H68O16S/c1-21-22(17-53-35-34(49)32(47)31(46)25(16-42)56-35)8-13-41(19-43)15-14-39(4)23(29(21)41)6-7-27-37(2)11-10-28(57-36-33(48)30(45)24(44)18-54-36)38(3,20-55-58(50,51)52)26(37)9-12-40(27,39)5/h8,21,23-36,42-49H,6-7,9-20H2,1-5H3,(H,50,51,52)

InChI Key

RBHJQJQPNRFRHI-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
Zygophyllum fabago	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
Steroid
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Sulfuric acid monoester
Sulfate-ester
Alkyl sulfate
Sulfuric acid ester
Organic sulfuric acid or derivatives
Secondary alcohol
Polyol
Oxacycle
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
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	0.53	ALOGPS
logP	-0.72	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	-1.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	262.36 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	206.16 m³·mol⁻¹	ChemAxon
Polarizability	91.16 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

74929107

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid (NP0254490)

MOL for NP0254490 ([8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid)

3D MOL for NP0254490 ([8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid)

3D SDF for NP0254490 ([8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid)

3D-SDF for NP0254490 ([8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid)

PDB for NP0254490 ([8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid)

3D PDB for NP0254490 ([8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid)

SMILES for NP0254490 ([8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid)

INCHI for NP0254490 ([8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid)

Structure for NP0254490 ([8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid)

3D Structure for NP0254490 ([8a-(hydroxymethyl)-4,6a,6b,12,14b-pentamethyl-11-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]-2,3,4a,5,6,7,8,9,12,12a,12b,13,14,14a-tetradecahydro-1h-picen-4-yl]methoxysulfonic acid)