NP-MRD: Showing NP-Card for Kudzusaponin SA3 (NP0336898)

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Record Information

Version

2.0

Created at

2024-09-11 08:20:33 UTC

Updated at

2024-09-11 08:20:33 UTC

NP-MRD ID

NP0336898

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kudzusaponin SA3

Description

Kudzusaponin SA3 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 SA3 was first documented in 1997 (PMID: 9331982). Based on a literature review very few articles have been published on Kudzusaponin SA3.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262310522D          

 76 84  0  0  0  0            999 V2000
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    0.3574    0.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv2104 05262310522D          

 76 84  0  0  0  0            999 V2000
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 12 13  1  0  0  0  0
 12 47  1  0  0  0  0
 13 14  1  0  0  0  0
 13 54  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 56  1  0  0  0  0
 16 17  1  0  0  0  0
 16 62  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 69  1  0  0  0  0
 19 20  1  0  0  0  0
 19 74  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  1  0  0  0  0
 23 37  1  0  0  0  0
 24 25  1  0  0  0  0
 24 34  1  0  0  0  0
 25 26  2  0  0  0  0
 25 31  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 31  1  0  0  0  0
 29 76  1  0  0  0  0
 30 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
 34 35  1  0  0  0  0
 34 41  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 40  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 64  1  0  0  0  0
 44 45  1  0  0  0  0
 44 68  1  0  0  0  0
 45 46  1  0  0  0  0
 45 66  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 53  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  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
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 61  1  0  0  0  0
 58 59  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 70 73  1  0  0  0  0
 72 73  1  0  0  0  0
 73 74  1  0  0  0  0
 74 75  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336898

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2C(O)C(O)C(CO)OC2OC2C(O)C(O)C(OC2OC2CCC3(C)C(CCC4(C)C3CC=C3C5CC(C)(C)C(O)C(OC6OCC(O)C(O)C6O)C5(C)CCC43C)C2(C)CO)C(O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1/C53H86O23/c1-21-29(57)32(60)37(65)45(70-21)74-39-33(61)31(59)25(18-54)71-46(39)75-40-35(63)34(62)38(43(67)68)73-47(40)72-28-12-13-50(5)26(51(28,6)20-55)11-14-53(8)27(50)10-9-22-23-17-48(2,3)41(66)42(49(23,4)15-16-52(22,53)7)76-44-36(64)30(58)24(56)19-69-44/h9,21,23-42,44-47,54-66H,10-20H2,1-8H3,(H,67,68)

> <INCHI_KEY>
CYENWVJHJXHASB-UHFFFAOYNA-N

> <FORMULA>
C53H86O23

> <MOLECULAR_WEIGHT>
1091.248

> <EXACT_MASS>
1090.555989029

> <JCHEM_ACCEPTOR_COUNT>
23

> <JCHEM_ATOM_COUNT>
162

> <JCHEM_AVERAGE_POLARIZABILITY>
114.42852132814053

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-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

> <JCHEM_LOGP>
-1.113260672333336

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.910935346405479

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.317895772193384

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6765067029896046

> <JCHEM_POLAR_SURFACE_AREA>
374.13000000000005

> <JCHEM_REFRACTIVITY>
258.4194000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-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                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0       2.002   1.721   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667   0.951   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667   1.721   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.999   0.951   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.011  -0.230   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667   4.801   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.667   3.261   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.999   4.031   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.334   3.261   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.334   1.721   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.666   0.951   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.000   1.721   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.335   0.951   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -7.335  -0.589   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -8.667  -1.359   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.667  -2.899   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -7.335  -3.669   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -7.335  -5.209   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.000  -5.979   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.666  -5.209   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.990  -0.230   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.507   0.037   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.668   7.878   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.668   6.338   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.334   5.571   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.002   6.341   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.667   5.571   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.667   4.031   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.002   3.258   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.334   2.488   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.334   4.028   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.668   3.258   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.000   4.028   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.000   5.568   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.335   4.798   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.991   9.828   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.000   8.648   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.012   9.828   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       8.670   8.648   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       7.335   7.878   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       7.335   6.338   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       8.670   5.568   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      10.002   6.338   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      11.336   5.568   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      12.671   6.338   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      14.003   5.568   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -6.000   3.261   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -7.335   4.031   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -7.335   5.571   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -6.000   6.341   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -8.667   6.341   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0     -10.002   4.031   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -8.667   3.261   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -8.667   1.721   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0     -10.002   0.951   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0     -10.002  -0.589   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0     -11.336  -1.359   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0     -12.668  -0.589   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0     -14.003  -1.359   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0     -12.668  -3.669   0.000  0.00  0.00           O+0
HETATM   61  C   UNK     0     -11.336  -2.899   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0     -10.002  -3.669   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0     -10.002  -5.209   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      10.002   7.878   0.000  0.00  0.00           O+0
HETATM   65  C   UNK     0      11.336   8.648   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      12.671   7.878   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      14.003   8.648   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      11.336   4.028   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0      -8.667  -5.979   0.000  0.00  0.00           O+0
HETATM   70  C   UNK     0      -8.667  -7.519   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0     -10.002  -8.288   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0      -7.335  -9.828   0.000  0.00  0.00           O+0
HETATM   73  C   UNK     0      -7.335  -8.288   0.000  0.00  0.00           C+0
HETATM   74  C   UNK     0      -6.000  -7.519   0.000  0.00  0.00           C+0
HETATM   75  O   UNK     0      -4.666  -8.288   0.000  0.00  0.00           O+0
HETATM   76  C   UNK     0       1.990   4.801   0.000  0.00  0.00           C+0
CONECT    1    2   29                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5   10   21                                             
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    3    6    8   28                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    4    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   47                                                  
CONECT   13   12   14   54                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   56                                                  
CONECT   16   15   17   62                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   69                                                  
CONECT   19   18   20   74                                                  
CONECT   20   19                                                            
CONECT   21    4   22                                                       
CONECT   22   21                                                            
CONECT   23   24   37                                                       
CONECT   24   23   25   34                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28    7   27   29                                                  
CONECT   29    1   28   31   76                                             
CONECT   30   31                                                            
CONECT   31   25   29   30   32                                             
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   24   33   35   41                                             
CONECT   35   34                                                            
CONECT   36   37                                                            
CONECT   37   23   36   38   40                                             
CONECT   38   37                                                            
CONECT   39   40                                                            
CONECT   40   37   39   41                                                  
CONECT   41   34   40   42                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   64                                                  
CONECT   44   43   45   68                                                  
CONECT   45   44   46   66                                                  
CONECT   46   45                                                            
CONECT   47   12   48                                                       
CONECT   48   47   49   53                                                  
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49                                                            
CONECT   52   53                                                            
CONECT   53   48   52   54                                                  
CONECT   54   13   53   55                                                  
CONECT   55   54                                                            
CONECT   56   15   57                                                       
CONECT   57   56   58   61                                                  
CONECT   58   57   59                                                       
CONECT   59   58                                                            
CONECT   60   61                                                            
CONECT   61   57   60   62                                                  
CONECT   62   16   61   63                                                  
CONECT   63   62                                                            
CONECT   64   43   65                                                       
CONECT   65   64   66                                                       
CONECT   66   45   65   67                                                  
CONECT   67   66                                                            
CONECT   68   44                                                            
CONECT   69   18   70                                                       
CONECT   70   69   71   73                                                  
CONECT   71   70                                                            
CONECT   72   73                                                            
CONECT   73   70   72   74                                                  
CONECT   74   19   73   75                                                  
CONECT   75   74                                                            
CONECT   76   29                                                            
MASTER        0    0    0    0    0    0    0    0   76    0  168    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₃H₈₆O₂₃

Average Mass

1091.2480 Da

Monoisotopic Mass

1090.55599 Da

IUPAC Name

5-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-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

5-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-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

CAS Registry Number

Not Available

SMILES

CC1OC(OC2C(O)C(O)C(CO)OC2OC2C(O)C(O)C(OC2OC2CCC3(C)C(CCC4(C)C3CC=C3C5CC(C)(C)C(O)C(OC6OCC(O)C(O)C6O)C5(C)CCC43C)C2(C)CO)C(O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1/C53H86O23/c1-21-29(57)32(60)37(65)45(70-21)74-39-33(61)31(59)25(18-54)71-46(39)75-40-35(63)34(62)38(43(67)68)73-47(40)72-28-12-13-50(5)26(51(28,6)20-55)11-14-53(8)27(50)10-9-22-23-17-48(2,3)41(66)42(49(23,4)15-16-52(22,53)7)76-44-36(64)30(58)24(56)19-69-44/h9,21,23-42,44-47,54-66H,10-20H2,1-8H3,(H,67,68)

InChI Key

CYENWVJHJXHASB-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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
Oligosaccharide
Steroid
Fatty acyl glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Fatty acyl
Hydroxy acid
Pyran
Oxane
Cyclic alcohol
Secondary alcohol
Acetal
Polyol
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Organoheterocyclic compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen 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	-1.1	ChemAxon
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	14	ChemAxon
Polar Surface Area	374.13 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	258.42 m³·mol⁻¹	ChemAxon
Polarizability	114.43 Å³	ChemAxon
Number of Rings	9	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Arao T, Udayama M, Kinjo J, Nohara T, Funakoshi T, Kojima S: Preventive effects of saponins from puerariae radix (the root of Pueraria lobata Ohwi) on in vitro immunological injury of rat primary hepatocyte cultures. Biol Pharm Bull. 1997 Sep;20(9):988-91. doi: 10.1248/bpb.20.988. [PubMed:9331982 ]

Showing NP-Card for Kudzusaponin SA3 (NP0336898)

MOL for NP0336898 (Kudzusaponin SA3)

3D MOL for NP0336898 (Kudzusaponin SA3)

3D SDF for NP0336898 (Kudzusaponin SA3)

3D-SDF for NP0336898 (Kudzusaponin SA3)

PDB for NP0336898 (Kudzusaponin SA3)

3D PDB for NP0336898 (Kudzusaponin SA3)

SMILES for NP0336898 (Kudzusaponin SA3)

INCHI for NP0336898 (Kudzusaponin SA3)

Structure for NP0336898 (Kudzusaponin SA3)

3D Structure for NP0336898 (Kudzusaponin SA3)