NP-MRD: Showing NP-Card for 5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-{[10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}oxane-2-carboxylic acid (NP0327709)

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Record Information

Version

2.0

Created at

2022-09-12 10:32:13 UTC

Updated at

2022-09-12 10:32:13 UTC

NP-MRD ID

NP0327709

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Kudzusaponin SA4 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. Kudzusaponin SA4 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Kudzusaponin SA4 has been detected, but not quantified in, pulses. 5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-{[10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}oxane-2-carboxylic acid is found in Pueraria montana. This could make kudzusaponin SA4 a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241209202D          

 67 74  0  0  0  0            999 V2000
    0.6600   -0.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0550   -0.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7686   -0.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4836   -0.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9530   -1.3613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7686    1.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7686    0.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4836    0.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1986    0.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1986   -0.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9124   -0.7288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6274   -0.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6274    0.5087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.7711    0.9212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8271   -1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6274    2.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3410    1.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0561    2.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7711   -0.7288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3410   -0.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3410   -1.5538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0561   -1.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7711   -1.5538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.9148   -1.9663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0886    2.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3736    1.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6600    2.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6600    0.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3410   -3.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0561   -2.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.1997   -3.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3736    0.0962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0886    0.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036    0.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036    1.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173    1.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3330    4.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036    3.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2729    4.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2323    3.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5173    2.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2323    1.7462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7711   -4.0289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0725   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8549    1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6785    1.0326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0897    1.7462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6785    2.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8549    2.4572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4423    0.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0897    0.3176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9148    1.7462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1997   -0.7288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 37  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  4 17  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 36  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
 12 24  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 20  1  0  0  0  0
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 15 23  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  2  0  0  0  0
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 24 25  1  0  0  0  0
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 26 27  1  0  0  0  0
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 31 32  1  0  0  0  0
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 33 44  1  0  0  0  0
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 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 47 54  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 53  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 63  1  0  0  0  0
 59 60  1  0  0  0  0
 59 64  1  0  0  0  0
 60 61  1  0  0  0  0
 60 65  1  0  0  0  0
 61 62  1  0  0  0  0
 61 66  1  0  0  0  0
 62 63  1  0  0  0  0
M  END

     RDKit          3D

141148  0  0  0  0  0  0  0  0999 V2000
   -4.3174    2.2117    3.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5931    1.6941    1.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5888    2.9343    1.0790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6457    0.6593    1.5091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1923   -0.7265    1.2991 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0775   -1.5533    0.7752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1430   -1.9345    1.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0234   -2.7530    1.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4519   -2.1030   -0.0997 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241209202D          

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M  END
> <DATABASE_ID>
NP0327709

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC2C3=CCC4C5(C)CCC(OC6OC(C(O)C(O)C6OC6OC(C(O)C(O)C6O)C(O)=O)C(O)=O)C(C)(CO)C5CCC4(C)C3(C)CCC2(C)C(OC2OCC(O)C(O)C2O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C47H74O20/c1-42(2)16-20-19-8-9-23-44(4)12-11-24(63-41-34(29(54)28(53)33(65-41)38(60)61)66-40-31(56)26(51)27(52)32(64-40)37(58)59)45(5,18-48)22(44)10-13-47(23,7)46(19,6)15-14-43(20,3)36(35(42)57)67-39-30(55)25(50)21(49)17-62-39/h8,20-36,39-41,48-57H,9-18H2,1-7H3,(H,58,59)(H,60,61)

> <INCHI_KEY>
RPEKPENNMFTVPA-UHFFFAOYSA-N

> <FORMULA>
C47H74O20

> <MOLECULAR_WEIGHT>
959.0785

> <EXACT_MASS>
958.477344808

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
101.58521709290349

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
-0.06906045533333288

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.5877559082227393

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.957326780714167

> <JCHEM_PKA_STRONGEST_BASIC>
-3.731980846359378

> <JCHEM_POLAR_SURFACE_AREA>
332.28

> <JCHEM_REFRACTIVITY>
227.41720000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.76e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       1.232  -0.590   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.103  -1.360   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.435  -0.590   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.769  -1.360   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.779  -2.541   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.435   2.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.435   0.950   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.769   1.720   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.104   0.950   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.104  -0.590   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.436  -1.360   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.771  -0.590   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.771   0.950   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -8.103   1.720   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -9.438   0.950   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -10.773   1.720   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.760  -2.541   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.277  -2.271   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.771   4.030   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -8.103   3.260   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -9.438   4.030   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0     -10.773  -1.360   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -9.438  -0.590   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.103  -1.360   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -8.103  -2.900   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -9.438  -3.670   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -10.773  -2.900   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0     -12.105  -3.670   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -13.439  -2.900   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -14.774  -3.670   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.899   5.570   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.899   4.030   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.564   3.260   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.232   4.030   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -0.103   3.260   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.103   1.720   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.232   0.950   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -8.103  -5.981   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -9.438  -5.210   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0     -10.773  -5.981   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0     -12.105  -5.210   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0     -13.439  -5.981   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.564   0.180   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.564   1.720   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       3.899   0.950   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.233   1.720   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.233   3.260   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.566   2.490   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       6.222   7.521   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.233   6.340   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       4.243   7.521   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       7.900   6.340   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       6.566   5.570   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       6.566   4.030   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0       7.900   3.260   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0     -10.773  -7.521   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       2.002  -0.385   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      10.159   3.260   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      10.929   1.928   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      12.467   1.928   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      13.234   3.260   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      12.467   4.587   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      10.929   4.587   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      10.159   0.593   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      13.234   0.593   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      14.774   3.260   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0     -13.439  -1.360   0.000  0.00  0.00           O+0
CONECT    1    2   37                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5   10   17                                             
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    3    6    8   36                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    4    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17                                                            
CONECT   19   20                                                            
CONECT   20   14   19   21                                                  
CONECT   21   20                                                            
CONECT   22   23                                                            
CONECT   23   15   22   24                                                  
CONECT   24   12   23   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   39                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   41                                                  
CONECT   29   28   30   67                                                  
CONECT   30   29                                                            
CONECT   31   32   50                                                       
CONECT   32   31   33   47                                                  
CONECT   33   32   34   44                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36    7   35   37                                                  
CONECT   37    1   36   44   57                                             
CONECT   38   39                                                            
CONECT   39   26   38   40                                                  
CONECT   40   39   41   56                                                  
CONECT   41   28   40   42                                                  
CONECT   42   41                                                            
CONECT   43   44                                                            
CONECT   44   33   37   43   45                                             
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   32   46   48   54                                             
CONECT   48   47                                                            
CONECT   49   50                                                            
CONECT   50   31   49   51   53                                             
CONECT   51   50                                                            
CONECT   52   53                                                            
CONECT   53   50   52   54                                                  
CONECT   54   47   53   55                                                  
CONECT   55   54   58                                                       
CONECT   56   40                                                            
CONECT   57   37                                                            
CONECT   58   55   59   63                                                  
CONECT   59   58   60   64                                                  
CONECT   60   59   61   65                                                  
CONECT   61   60   62   66                                                  
CONECT   62   61   63                                                       
CONECT   63   58   62                                                       
CONECT   64   59                                                            
CONECT   65   60                                                            
CONECT   66   61                                                            
CONECT   67   29                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  148    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₄₇H₇₄O₂₀

Average Mass

959.0785 Da

Monoisotopic Mass

958.47734 Da

IUPAC Name

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

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1(C)CC2C3=CCC4C5(C)CCC(OC6OC(C(O)C(O)C6OC6OC(C(O)C(O)C6O)C(O)=O)C(O)=O)C(C)(CO)C5CCC4(C)C3(C)CCC2(C)C(OC2OCC(O)C(O)C2O)C1O

InChI Identifier

InChI=1S/C47H74O20/c1-42(2)16-20-19-8-9-23-44(4)12-11-24(63-41-34(29(54)28(53)33(65-41)38(60)61)66-40-31(56)26(51)27(52)32(64-40)37(58)59)45(5,18-48)22(44)10-13-47(23,7)46(19,6)15-14-43(20,3)36(35(42)57)67-39-30(55)25(50)21(49)17-62-39/h8,20-36,39-41,48-57H,9-18H2,1-7H3,(H,58,59)(H,60,61)

InChI Key

RPEKPENNMFTVPA-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
Pueraria montana	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
Beta-hydroxy acid
Pyran
Oxane
Hydroxy acid
Dicarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Organoheterocyclic compound
Polyol
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Acetal
Primary alcohol
Organic oxygen compound
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
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	1.49	ALOGPS
logP	-0.069	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	332.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	227.42 m³·mol⁻¹	ChemAxon
Polarizability	101.59 Å³	ChemAxon
Number of Rings	8	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

HMDB0031353

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003419

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

85221187

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]-3,4-dihydroxy-6-{[10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}oxane-2-carboxylic acid (NP0327709)

MOL for NP0327709 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-{[10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}oxane-2-carboxylic acid)

3D MOL for NP0327709 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-{[10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}oxane-2-carboxylic acid)

3D SDF for NP0327709 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-{[10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}oxane-2-carboxylic acid)

3D-SDF for NP0327709 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-{[10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}oxane-2-carboxylic acid)

PDB for NP0327709 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-{[10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}oxane-2-carboxylic acid)

3D PDB for NP0327709 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-{[10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}oxane-2-carboxylic acid)

SMILES for NP0327709 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-{[10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}oxane-2-carboxylic acid)

INCHI for NP0327709 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-{[10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}oxane-2-carboxylic acid)

Structure for NP0327709 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-{[10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}oxane-2-carboxylic acid)

3D Structure for NP0327709 (5-[(6-carboxy-3,4,5-trihydroxyoxan-2-yl)oxy]-3,4-dihydroxy-6-{[10-hydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-9-[(3,4,5-trihydroxyoxan-2-yl)oxy]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}oxane-2-carboxylic acid)