NP-MRD: Showing NP-Card for Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside] (NP0049426)

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Record Information

Version

2.0

Created at

2022-03-17 21:12:22 UTC

Updated at

2022-03-17 21:12:22 UTC

NP-MRD ID

NP0049426

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside]

Description

Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside], also known as medicagenic acid 3-O-triglucoside, 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. Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside] is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside] has been detected, but not quantified in, alfalfa and cereals and cereal products. This could make medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside] a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241218542D          

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M  END


  Mrv0541 02241218542D          

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 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 63  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 65  1  0  0  0  0
 42 43  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 67  1  0  0  0  0
 47 48  1  0  0  0  0
 49 50  1  0  0  0  0
 49 60  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  2  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 69  1  0  0  0  0
 56 57  2  0  0  0  0
 57 58  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 64 68  1  0  0  0  0
 65 66  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049426

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(OC6OC(CO)C(O)C(OC7OC(COC8OC(CO)C(O)C(O)C8O)C(O)C(O)C7O)C6O)C(C)(C5CCC34C)C(O)=O)C2C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C48H76O21/c1-43(2)11-13-48(42(62)63)14-12-45(4)20(21(48)15-43)7-8-26-44(3)16-22(51)37(47(6,41(60)61)27(44)9-10-46(26,45)5)69-40-35(59)36(30(54)24(18-50)66-40)68-39-34(58)32(56)29(53)25(67-39)19-64-38-33(57)31(55)28(52)23(17-49)65-38/h7,21-40,49-59H,8-19H2,1-6H3,(H,60,61)(H,62,63)

> <INCHI_KEY>
HIZNXZVTIKIPSM-UHFFFAOYSA-N

> <FORMULA>
C48H76O21

> <MOLECULAR_WEIGHT>
989.1044

> <EXACT_MASS>
988.487909494

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
105.03065666949358

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylic acid

> <ALOGPS_LOGP>
0.62

> <JCHEM_LOGP>
-0.6008845116666646

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.83662124428013

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.026605728492716

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6552454372455507

> <JCHEM_POLAR_SURFACE_AREA>
352.51

> <JCHEM_REFRACTIVITY>
233.9431000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic 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      11.335   2.468   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.335   0.928   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.003   0.158   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.003  -1.382   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.668  -2.152   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.334  -1.382   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.334  -2.922   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.002  -3.692   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.667  -4.462   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.335  -3.692   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.335  -2.152   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.335  -0.612   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.991  -5.642   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.001  -4.462   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.010  -5.642   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.507  -5.373   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.001  -1.382   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.666  -2.152   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.666  -1.382   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.666  -3.692   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.666  -4.462   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.001  -3.692   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.001  -2.152   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.335  -1.382   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.335   0.158   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.667   0.928   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -3.335  -6.002   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.335  -4.462   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.667  -3.692   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -4.667  -2.152   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.002  -1.382   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.536  -7.087   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -6.002  -4.462   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -7.334  -3.692   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -7.334  -2.152   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -8.668  -1.382   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -8.668   0.158   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0     -10.003   0.928   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0     -10.003   2.468   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -8.668   3.237   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      -8.668   4.777   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -7.334   5.547   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -7.334   7.087   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -8.668  -6.002   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -8.668  -4.462   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -10.003  -3.692   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -10.003  -2.152   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0     -11.335  -1.382   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       8.668   2.468   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.668   0.928   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       7.334   0.158   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.002   0.928   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       4.667   0.158   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       4.667  -1.382   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       6.002  -2.152   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      11.335  -2.152   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      11.335  -0.612   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      12.670   0.158   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      10.991   4.418   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      10.003   3.237   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       9.012   4.418   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0     -12.670   2.468   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0     -11.335   3.237   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0     -11.335   4.777   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0     -10.003   5.547   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0     -10.003   7.087   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0     -11.335  -4.462   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0     -12.670   5.547   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0       6.772  -3.487   0.000  0.00  0.00           C+0
CONECT    1    2   60                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   50   57                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   51   55                                             
CONECT    7    6                                                            
CONECT    8    9   55                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   17   54                                             
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14   10   13   15   20                                             
CONECT   15   14   16   32                                                  
CONECT   16   15                                                            
CONECT   17   11   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   14   18   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   28                                                            
CONECT   28   22   27   29                                                  
CONECT   29   28   30   33                                                  
CONECT   30   24   29   31                                                  
CONECT   31   30                                                            
CONECT   32   15                                                            
CONECT   33   29   34                                                       
CONECT   34   33   35   45                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   47                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   63                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   65                                                  
CONECT   42   41   43                                                       
CONECT   43   42                                                            
CONECT   44   45                                                            
CONECT   45   34   44   46                                                  
CONECT   46   45   47   67                                                  
CONECT   47   36   46   48                                                  
CONECT   48   47                                                            
CONECT   49   50   60                                                       
CONECT   50    3   49   51                                                  
CONECT   51    6   50   52                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   11   53   55                                                  
CONECT   55    6    8   54   69                                             
CONECT   56   57                                                            
CONECT   57    3   56   58                                                  
CONECT   58   57                                                            
CONECT   59   60                                                            
CONECT   60    1   49   59   61                                             
CONECT   61   60                                                            
CONECT   62   63                                                            
CONECT   63   39   62   64                                                  
CONECT   64   63   65   68                                                  
CONECT   65   41   64   66                                                  
CONECT   66   65                                                            
CONECT   67   46                                                            
CONECT   68   64                                                            
CONECT   69   55                                                            
MASTER        0    0    0    0    0    0    0    0   69    0  152    0
END

View in JSmol

Synonyms

Value	Source
Medicagenate 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside]	Generator
Medicagenic acid 3-O-triglucoside	HMDB
3-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylate	Generator

Chemical Formula

C₄₈H₇₆O₂₁

Average Mass

989.1044 Da

Monoisotopic Mass

988.48791 Da

IUPAC Name

3-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4,8a-dicarboxylic acid

Traditional Name

3-{[3,5-dihydroxy-6-(hydroxymethyl)-4-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid

CAS Registry Number

37838-43-0

SMILES

CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CC(O)C(OC6OC(CO)C(O)C(OC7OC(COC8OC(CO)C(O)C(O)C8O)C(O)C(O)C7O)C6O)C(C)(C5CCC34C)C(O)=O)C2C1)C(O)=O

InChI Identifier

InChI=1S/C48H76O21/c1-43(2)11-13-48(42(62)63)14-12-45(4)20(21(48)15-43)7-8-26-44(3)16-22(51)37(47(6,41(60)61)27(44)9-10-46(26,45)5)69-40-35(59)36(30(54)24(18-50)66-40)68-39-34(58)32(56)29(53)25(67-39)19-64-38-33(57)31(55)28(52)23(17-49)65-38/h7,21-40,49-59H,8-19H2,1-6H3,(H,60,61)(H,62,63)

InChI Key

HIZNXZVTIKIPSM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Medicago sativa	FooDB	KNAPSACK

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
Oligosaccharide
12-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
Steroid
Fatty acyl glycoside
Glycosyl compound
O-glycosyl compound
Dicarboxylic acid or derivatives
Fatty acyl
Oxane
Cyclic alcohol
Secondary alcohol
Acetal
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Alcohol
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	0.62	ALOGPS
logP	-0.6	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	352.51 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	233.94 m³·mol⁻¹	ChemAxon
Polarizability	105.03 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

HMDB0039487

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB019093

KNApSAcK ID

C00003533

Chemspider ID

3681490

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4483634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside] (NP0049426)

MOL for NP0049426 (Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside])

3D MOL for NP0049426 (Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside])

3D SDF for NP0049426 (Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside])

3D-SDF for NP0049426 (Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside])

PDB for NP0049426 (Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside])

3D PDB for NP0049426 (Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside])

SMILES for NP0049426 (Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside])

INCHI for NP0049426 (Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside])

Structure for NP0049426 (Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside])

3D Structure for NP0049426 (Medicagenic acid 3-O-[b-D-glucosyl-(1->6)-b-D-glucosyl-(1->3)-b-D-glucoside])