NP-MRD: Showing NP-Card for 5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid (NP0266140)

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Record Information

Version

2.0

Created at

2022-09-08 10:22:35 UTC

Updated at

2022-09-08 10:22:35 UTC

NP-MRD ID

NP0266140

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

Description

Licoricesaponin J2 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. Licoricesaponin J2 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Licoricesaponin J2 has been detected, but not quantified in, herbs and spices. 5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid is found in Glycyrrhiza uralensis. This could make licoricesaponin J2 a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061311092D          

 58 64  0  0  0  0            999 V2000
    0.5151   -1.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7598    0.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8019   -1.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9861   -4.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6585   -2.9433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3804   -1.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3730   -0.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0874   -1.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0874   -3.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2309   -2.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164   -2.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3730   -3.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151   -0.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5151   -0.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2296   -2.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9440   -2.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9440   -0.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0466   -4.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6585   -1.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9440   -0.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8019   -3.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0874   -2.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2308   -3.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2308   -0.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9453    0.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0887   -2.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3742   -2.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2308   -0.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6598   -0.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0887   -3.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6598   -2.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3742    0.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8032   -3.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9453   -1.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6598   -3.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6992    0.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2295   -1.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2296    0.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8019   -2.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164   -3.7683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6585   -2.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3729   -2.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7645   -5.1755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164    0.3567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9453    1.1817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8032   -2.1183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3743   -1.2933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5163   -1.2933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0887   -0.0558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3743    1.1817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5177   -3.3558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8032   -4.5933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9814    1.7639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1133    0.8454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9453   -3.7683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6598   -0.8808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3743   -3.7683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9453   -2.1183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  9  1  0  0  0  0
 14 13  1  0  0  0  0
 16 15  1  0  0  0  0
 19  7  2  0  0  0  0
 20 17  1  0  0  0  0
 20 19  1  0  0  0  0
 21  9  1  0  0  0  0
 22  8  1  0  0  0  0
 23 10  1  0  0  0  0
 25 24  1  0  0  0  0
 27 26  1  0  0  0  0
 28 24  1  0  0  0  0
 29 25  1  0  0  0  0
 30 26  1  0  0  0  0
 31 27  1  0  0  0  0
 32 29  1  0  0  0  0
 33 30  1  0  0  0  0
 34 28  1  0  0  0  0
 35 31  1  0  0  0  0
 37  1  1  0  0  0  0
 37 13  1  0  0  0  0
 37 15  1  0  0  0  0
 37 20  1  0  0  0  0
 38  2  1  0  0  0  0
 38 14  1  0  0  0  0
 38 17  1  0  0  0  0
 38 36  1  0  0  0  0
 39  3  1  0  0  0  0
 39 11  1  0  0  0  0
 39 21  1  0  0  0  0
 39 22  1  0  0  0  0
 40  4  1  0  0  0  0
 40 18  1  0  0  0  0
 40 21  1  0  0  0  0
 40 23  1  0  0  0  0
 41  5  1  0  0  0  0
 41 16  1  0  0  0  0
 41 19  1  0  0  0  0
 42  6  1  0  0  0  0
 42 12  1  0  0  0  0
 42 22  1  0  0  0  0
 42 41  1  0  0  0  0
 43 18  1  0  0  0  0
 44 24  1  0  0  0  0
 45 25  1  0  0  0  0
 46 26  1  0  0  0  0
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 48 28  1  0  0  0  0
 49 32  2  0  0  0  0
 50 32  1  0  0  0  0
 51 33  2  0  0  0  0
 52 33  1  0  0  0  0
 53 36  2  0  0  0  0
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 55 23  1  0  0  0  0
 55 35  1  0  0  0  0
 56 29  1  0  0  0  0
 56 34  1  0  0  0  0
 57 30  1  0  0  0  0
 57 35  1  0  0  0  0
 58 31  1  0  0  0  0
 58 34  1  0  0  0  0
M  END

     RDKit          3D

122128  0  0  0  0  0  0  0  0999 V2000
   -0.5737   -1.3872    2.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7748   -0.5688    1.0141 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.4497    0.5047    0.3764 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0635   -0.8365    0.0732 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0274   -0.7086   -0.9182 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3219   -0.9419   -0.5550 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9691   -1.9174   -1.2505 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6380   -1.5637   -2.3824 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4506   -2.5451   -3.4900 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0647   -2.3155   -4.6952 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4571    0.9157   -2.2778 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0958    0.3964   -0.6356 C   0  0  2  0  0  0  0  0  0  0  0  0
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    8.0919    1.5237    0.0889 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3437    2.4150    1.1341 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.3198    3.4411    0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4027   -2.4043   -0.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9542   -0.3978   -0.3106 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6852    0.7005   -1.3536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1884   -0.0600    0.8995 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9647   -0.1709    2.1952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2801    0.5011    2.0512 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.2610    1.0517    0.8384 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.4103    0.1037    1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6896    0.9050    1.1169 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.1049   -0.9471    3.1661 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2679    0.9726   -0.6395 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061311092D          

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M  END
> <DATABASE_ID>
NP0266140

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC(C)(CC1C1=CCC3C4(C)CCC(OC5OC(C(O)C(O)C5OC5OC(C(O)C(O)C5O)C(O)=O)C(O)=O)C(C)(CO)C4CCC3(C)C1(C)CC2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C42H64O16/c1-37-13-14-38(2,36(53)54)17-20(37)19-7-8-22-39(3)11-10-23(40(4,18-43)21(39)9-12-42(22,6)41(19,5)16-15-37)55-35-31(27(47)26(46)30(57-35)33(51)52)58-34-28(48)24(44)25(45)29(56-34)32(49)50/h7,20-31,34-35,43-48H,8-18H2,1-6H3,(H,49,50)(H,51,52)(H,53,54)

> <INCHI_KEY>
SLWCVFLNZDOMEZ-UHFFFAOYSA-N

> <FORMULA>
C42H64O16

> <MOLECULAR_WEIGHT>
824.948

> <EXACT_MASS>
824.419436

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
88.21636279669349

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
2.412940061333334

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.558246124295548

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9478869008132538

> <JCHEM_PKA_STRONGEST_BASIC>
-3.731980846359378

> <JCHEM_POLAR_SURFACE_AREA>
270.2

> <JCHEM_REFRACTIVITY>
199.96060000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.962  -3.184   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.285   1.846   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.964  -3.184   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.307  -8.214   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.963  -5.494   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.310  -3.211   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.296  -1.644   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.630  -2.414   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.630  -7.034   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.631  -4.724   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.297  -3.954   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.296  -6.264   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.962  -1.644   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.962  -0.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.295  -3.954   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.629  -4.724   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.629  -0.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.287  -8.214   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.963  -2.414   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.629  -1.644   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.964  -6.264   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.630  -3.954   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.631  -6.264   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.631  -0.104   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.965   0.666   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      16.966  -4.724   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.632  -3.954   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.631  -1.644   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.298  -0.104   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.966  -6.264   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      14.298  -4.724   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.632   0.666   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.299  -7.034   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.965  -2.414   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.298  -6.264   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.305   1.846   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.295  -2.414   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.295   0.666   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       8.964  -4.724   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      10.297  -7.034   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       4.963  -3.954   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.296  -4.724   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      10.760  -9.661   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      10.297   0.666   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      12.965   2.206   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      18.299  -3.954   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      15.632  -2.414   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      10.297  -2.414   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      16.966  -0.104   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      15.632   2.206   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      19.633  -6.264   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      18.299  -8.574   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       1.832   3.293   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      -0.211   1.578   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      12.965  -7.034   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      14.298  -1.644   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      15.632  -7.034   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      12.965  -3.954   0.000  0.00  0.00           O+0
CONECT    1   37                                                            
CONECT    2   38                                                            
CONECT    3   39                                                            
CONECT    4   40                                                            
CONECT    5   41                                                            
CONECT    6   42                                                            
CONECT    7    8   19                                                       
CONECT    8    7   22                                                       
CONECT    9   12   21                                                       
CONECT   10   11   23                                                       
CONECT   11   10   39                                                       
CONECT   12    9   42                                                       
CONECT   13   14   37                                                       
CONECT   14   13   38                                                       
CONECT   15   16   37                                                       
CONECT   16   15   41                                                       
CONECT   17   20   38                                                       
CONECT   18   40   43                                                       
CONECT   19    7   20   41                                                  
CONECT   20   17   19   37                                                  
CONECT   21    9   39   40                                                  
CONECT   22    8   39   42                                                  
CONECT   23   10   40   55                                                  
CONECT   24   25   28   44                                                  
CONECT   25   24   29   45                                                  
CONECT   26   27   30   46                                                  
CONECT   27   26   31   47                                                  
CONECT   28   24   34   48                                                  
CONECT   29   25   32   56                                                  
CONECT   30   26   33   57                                                  
CONECT   31   27   35   58                                                  
CONECT   32   29   49   50                                                  
CONECT   33   30   51   52                                                  
CONECT   34   28   56   58                                                  
CONECT   35   31   55   57                                                  
CONECT   36   38   53   54                                                  
CONECT   37    1   13   15   20                                             
CONECT   38    2   14   17   36                                             
CONECT   39    3   11   21   22                                             
CONECT   40    4   18   21   23                                             
CONECT   41    5   16   19   42                                             
CONECT   42    6   12   22   41                                             
CONECT   43   18                                                            
CONECT   44   24                                                            
CONECT   45   25                                                            
CONECT   46   26                                                            
CONECT   47   27                                                            
CONECT   48   28                                                            
CONECT   49   32                                                            
CONECT   50   32                                                            
CONECT   51   33                                                            
CONECT   52   33                                                            
CONECT   53   36                                                            
CONECT   54   36                                                            
CONECT   55   23   35                                                       
CONECT   56   29   34                                                       
CONECT   57   30   35                                                       
CONECT   58   31   34                                                       
MASTER        0    0    0    0    0    0    0    0   58    0  128    0
END

View in JSmol

Synonyms

Value	Source
6-[(6-Carboxy-2-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4,5-dihydroxyoxan-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylate	Generator

Chemical Formula

C₄₂H₆₄O₁₆

Average Mass

824.9480 Da

Monoisotopic Mass

824.41944 Da

IUPAC Name

5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC12CCC(C)(CC1C1=CCC3C4(C)CCC(OC5OC(C(O)C(O)C5OC5OC(C(O)C(O)C5O)C(O)=O)C(O)=O)C(C)(CO)C4CCC3(C)C1(C)CC2)C(O)=O

InChI Identifier

InChI=1S/C42H64O16/c1-37-13-14-38(2,36(53)54)17-20(37)19-7-8-22-39(3)11-10-23(40(4,18-43)21(39)9-12-42(22,6)41(19,5)16-15-37)55-35-31(27(47)26(46)30(57-35)33(51)52)58-34-28(48)24(44)25(45)29(56-34)32(49)50/h7,20-31,34-35,43-48H,8-18H2,1-6H3,(H,49,50)(H,51,52)(H,53,54)

InChI Key

SLWCVFLNZDOMEZ-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
Glycyrrhiza uralensis	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
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Disaccharide
Glycosyl compound
O-glycosyl compound
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Pyran
Oxane
Hydroxy acid
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
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	2.58	ALOGPS
logP	2.41	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	2.95	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	270.2 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	199.96 m³·mol⁻¹	ChemAxon
Polarizability	88.22 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

HMDB0039448

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019047

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

74029747

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid (NP0266140)

MOL for NP0266140 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid)

3D MOL for NP0266140 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid)

3D SDF for NP0266140 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid)

3D-SDF for NP0266140 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid)

PDB for NP0266140 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid)

3D PDB for NP0266140 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid)

SMILES for NP0266140 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid)

INCHI for NP0266140 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid)

Structure for NP0266140 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid)

3D Structure for NP0266140 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-6-{[11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid)