NP-MRD: Showing NP-Card for Soyasaponin A3 (NP0049175)

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Record Information

Version

2.0

Created at

2022-03-17 21:08:17 UTC

Updated at

2022-03-17 21:08:18 UTC

NP-MRD ID

NP0049175

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Soyasaponin A3

Description

Soyasaponin A3 belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. Soyasaponin A3 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Soyasaponin A3 has been detected, but not quantified in, pulses and soy beans. Soyasaponin A3 is found in Abrus pulchellus, Lupinus oreophilus, Pueraria montana and Sophora tonkinensis. This could make soyasaponin A3 a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241215452D          

 67 74  0  0  0  0            999 V2000
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M  END


  Mrv0541 02241215452D          

 67 74  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0049175

> <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(O)C5(C)CCC43C)C2(C)CO)C(O)=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C48H78O19/c1-20-27(51)29(53)33(57)40(62-20)66-35-30(54)28(52)23(18-49)63-41(35)67-36-32(56)31(55)34(39(60)61)65-42(36)64-26-12-13-45(5)24(46(26,6)19-50)11-14-48(8)25(45)10-9-21-22-17-43(2,3)37(58)38(59)44(22,4)15-16-47(21,48)7/h9,20,22-38,40-42,49-59H,10-19H2,1-8H3,(H,60,61)

> <INCHI_KEY>
NQGDGFITHGCDAO-UHFFFAOYSA-N

> <FORMULA>
C48H78O19

> <MOLECULAR_WEIGHT>
959.1215

> <EXACT_MASS>
958.513730314

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
101.43237328846665

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.48

> <JCHEM_LOGP>
0.027240031333333664

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.048865762032221

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.317895772495015

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648674430892787

> <JCHEM_POLAR_SURFACE_AREA>
315.21

> <JCHEM_REFRACTIVITY>
231.96860000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{[9,10-dihydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-5-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3,4-dihydroxyoxane-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       4.669   1.720   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.334   0.950   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.002   1.720   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.667   0.950   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.658  -0.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.002   4.800   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.002   3.260   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.667   4.030   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.667   3.260   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.667   1.720   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.999   0.950   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.334   1.720   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.334   3.260   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.666   4.030   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -6.001   3.260   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -7.336   4.030   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.323  -0.231   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.840   0.038   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.999  -5.210   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.334  -5.980   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.334  -7.520   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.999  -8.291   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -3.334   6.340   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.666   5.570   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.001   6.340   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -7.336   0.950   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.001   1.720   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.666   0.950   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.666  -0.590   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.001  -1.360   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -7.336  -0.590   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -8.668  -1.360   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.002  -0.590   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -11.337  -1.360   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -4.666  -9.831   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -4.666  -8.291   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -6.001  -7.520   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.336  -8.291   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.336   7.880   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.336   6.340   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       6.001   5.570   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       4.669   6.340   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.334   5.570   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       3.334   4.030   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.669   3.260   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -6.001  -5.980   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -4.666  -5.210   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      -4.666  -3.670   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -6.001  -2.900   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -7.336  -3.670   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -8.668  -2.900   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0     -10.002  -3.670   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       6.001   2.490   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       6.001   4.030   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       7.336   3.260   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       8.670   4.030   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       8.670   5.570   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      10.003   4.800   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       9.659   9.831   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0       8.670   8.650   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       7.680   9.831   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      11.337   8.650   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      10.003   7.880   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      10.003   6.340   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      11.337   5.570   0.000  0.00  0.00           O+0
HETATM   66  O   UNK     0      -7.336  -5.210   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0       5.439   1.925   0.000  0.00  0.00           C+0
CONECT    1    2   45                                                       
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   44                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    4    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   28                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   24                                                  
CONECT   15   14   16   27                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17                                                            
CONECT   19   20                                                            
CONECT   20   19   21   47                                                  
CONECT   21   20   22   36                                                  
CONECT   22   21                                                            
CONECT   23   24                                                            
CONECT   24   14   23   25                                                  
CONECT   25   24                                                            
CONECT   26   27                                                            
CONECT   27   15   26   28                                                  
CONECT   28   12   27   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   49                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   51                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   36                                                            
CONECT   36   21   35   37                                                  
CONECT   37   36   38   46                                                  
CONECT   38   37                                                            
CONECT   39   40   60                                                       
CONECT   40   39   41   57                                                  
CONECT   41   40   42   54                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44    7   43   45                                                  
CONECT   45    1   44   54   67                                             
CONECT   46   37   47                                                       
CONECT   47   20   46   48                                                  
CONECT   48   47   49                                                       
CONECT   49   30   48   50                                                  
CONECT   50   49   51   66                                                  
CONECT   51   32   50   52                                                  
CONECT   52   51                                                            
CONECT   53   54                                                            
CONECT   54   41   45   53   55                                             
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   40   56   58   64                                             
CONECT   58   57                                                            
CONECT   59   60                                                            
CONECT   60   39   59   61   63                                             
CONECT   61   60                                                            
CONECT   62   63                                                            
CONECT   63   60   62   64                                                  
CONECT   64   57   63   65                                                  
CONECT   65   64                                                            
CONECT   66   50                                                            
CONECT   67   45                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  148    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₄₈H₇₈O₁₉

Average Mass

959.1215 Da

Monoisotopic Mass

958.51373 Da

IUPAC Name

6-{[9,10-dihydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-5-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

Traditional Name

6-{[9,10-dihydroxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy}-5-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-3,4-dihydroxyoxane-2-carboxylic acid

CAS Registry Number

114077-04-2

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(O)C5(C)CCC43C)C2(C)CO)C(O)=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C48H78O19/c1-20-27(51)29(53)33(57)40(62-20)66-35-30(54)28(52)23(18-49)63-41(35)67-36-32(56)31(55)34(39(60)61)65-42(36)64-26-12-13-45(5)24(46(26,6)19-50)11-14-48(8)25(45)10-9-21-22-17-43(2,3)37(58)38(59)44(22,4)15-16-47(21,48)7/h9,20,22-38,40-42,49-59H,10-19H2,1-8H3,(H,60,61)

InChI Key

NQGDGFITHGCDAO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abrus pulchellus	LOTUS Database	35616633
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Lupinus oreophilus	LOTUS Database	35616633
Pueraria montana	LOTUS Database	35616633
Sophora tonkinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

o-Hydroxybenzoic acid esters

Alternative Parents

Substituents

O-hydroxybenzoic acid ester
Salicylic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.48	ALOGPS
logP	0.027	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	315.21 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	231.97 m³·mol⁻¹	ChemAxon
Polarizability	101.43 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

HMDB0038608

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017999

KNApSAcK ID

Not Available

Chemspider ID

164103

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

188847

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Soyasaponin A3 (NP0049175)

MOL for NP0049175 (Soyasaponin A3)

3D MOL for NP0049175 (Soyasaponin A3)

3D SDF for NP0049175 (Soyasaponin A3)

3D-SDF for NP0049175 (Soyasaponin A3)

PDB for NP0049175 (Soyasaponin A3)

3D PDB for NP0049175 (Soyasaponin A3)

SMILES for NP0049175 (Soyasaponin A3)

INCHI for NP0049175 (Soyasaponin A3)

Structure for NP0049175 (Soyasaponin A3)

3D Structure for NP0049175 (Soyasaponin A3)