NP-MRD: Showing NP-Card for Tomatoside A (NP0047848)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:57 UTC

Updated at

2022-03-17 20:46:57 UTC

NP-MRD ID

NP0047848

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tomatoside A

Description

Tomatoside A belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. Tomatoside A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, tomatoside a has been detected, but not quantified in, garden tomato. Tomatoside A is found in Tribulus terrestris. This could make tomatoside a a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241217332D          

 75 83  0  0  0  0            999 V2000
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M  END


  Mrv0541 02241217332D          

 75 83  0  0  0  0            999 V2000
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 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 42  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 28  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 37  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 39  1  0  0  0  0
 34 35  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 41  1  0  0  0  0
 39 40  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 49  1  0  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 45 52  1  0  0  0  0
 46 47  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  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
 54 69  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 56 71  1  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
 60 67  1  0  0  0  0
 61 62  1  0  0  0  0
 61 73  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 65 73  1  0  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 70 75  1  0  0  0  0
 71 72  1  0  0  0  0
 73 74  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047848

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC1(O)OC2CC3C4CCC5CC(CCC5(C)C4CCC3(C)C2C1C)OC1OC(CO)C(OC2OC(CO)C(O)C(O)C2OC2OC(CO)C(O)C(O)C2O)C(O)C1O)COC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C51H86O24/c1-20(19-67-45-40(63)36(59)33(56)28(15-52)69-45)7-12-51(66)21(2)32-27(75-51)14-26-24-6-5-22-13-23(8-10-49(22,3)25(24)9-11-50(26,32)4)68-46-42(65)39(62)43(31(18-55)72-46)73-48-44(38(61)35(58)30(17-54)71-48)74-47-41(64)37(60)34(57)29(16-53)70-47/h20-48,52-66H,5-19H2,1-4H3

> <INCHI_KEY>
OFEAYOYKIQKFSK-UHFFFAOYSA-N

> <FORMULA>
C51H86O24

> <MOLECULAR_WEIGHT>
1083.2141

> <EXACT_MASS>
1082.55090368

> <JCHEM_ACCEPTOR_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
114.31754930303842

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
15

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-({2-[(4,5-dihydroxy-6-{[6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-16-yl]oxy}-2-(hydroxymethyl)oxan-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.88

> <JCHEM_LOGP>
-2.9121612196666637

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.957362455943908

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.505128452299852

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6786119366911016

> <JCHEM_POLAR_SURFACE_AREA>
386.52000000000004

> <JCHEM_REFRACTIVITY>
252.57920000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.33e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-({2-[(4,5-dihydroxy-6-{[6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-16-yl]oxy}-2-(hydroxymethyl)oxan-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <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       5.221   2.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.698   0.905   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.792  -0.340   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.698  -1.585   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.792  -2.832   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.327  -2.355   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.995  -3.125   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.660  -2.355   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.660  -0.815   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.995  -0.045   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.327  -0.815   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.488   0.715   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.995  -4.665   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.660  -5.435   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.672  -4.665   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.007  -5.435   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.342  -4.665   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.342  -3.125   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.007  -2.355   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.672  -3.125   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.672  -1.585   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.161  -1.110   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.161   0.430   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.693   0.268   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.599   1.516   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.129   1.354   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.758  -0.053   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.482   1.936   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.035   2.599   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.568   2.440   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.474   3.684   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      16.003   3.523   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      16.910   4.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      18.442   4.608   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      19.346   5.853   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      12.315   5.253   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      13.845   5.091   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.751   6.338   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.283   6.177   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      17.189   7.422   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      14.125   7.745   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -4.674  -5.435   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      -6.009  -4.665   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -6.009  -3.125   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -7.341  -2.355   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -7.341  -0.815   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -8.676  -0.045   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -7.341  -6.975   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      -7.341  -5.435   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -8.676  -4.665   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0     -10.010  -5.435   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      -8.676  -3.125   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0     -10.010  -2.355   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0     -11.342  -3.125   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0     -11.342  -4.665   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0     -12.677  -5.435   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0     -12.677  -6.975   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0     -14.012  -7.745   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0     -12.677   2.265   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0     -14.012   1.495   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0     -15.344   2.265   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0     -15.344   3.805   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0     -19.346  -0.045   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0     -18.011  -0.815   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0     -16.679  -0.045   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0     -15.344  -0.815   0.000  0.00  0.00           O+0
HETATM   67  C   UNK     0     -14.012  -0.045   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0     -12.677  -0.815   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0     -12.677  -2.355   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0     -14.012  -3.125   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0     -14.012  -4.665   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0     -15.344  -5.435   0.000  0.00  0.00           O+0
HETATM   73  C   UNK     0     -16.679   1.495   0.000  0.00  0.00           C+0
HETATM   74  O   UNK     0     -18.011   2.265   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0     -15.344  -2.355   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   22                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    3    6   10   12                                             
CONECT   12   11                                                            
CONECT   13    7   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   42                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20    8   15   19   21                                             
CONECT   21   20                                                            
CONECT   22    4   23                                                       
CONECT   23    2   22   24   28                                             
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26                                                            
CONECT   28   23                                                            
CONECT   29   26   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   39                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   37                                                            
CONECT   37   31   36   38                                                  
CONECT   38   37   39   41                                                  
CONECT   39   33   38   40                                                  
CONECT   40   39                                                            
CONECT   41   38                                                            
CONECT   42   17   43                                                       
CONECT   43   42   44   49                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   52                                                  
CONECT   46   45   47                                                       
CONECT   47   46                                                            
CONECT   48   49                                                            
CONECT   49   43   48   50                                                  
CONECT   50   49   51   52                                                  
CONECT   51   50                                                            
CONECT   52   45   50   53                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55   69                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57   71                                                  
CONECT   57   56   58                                                       
CONECT   58   57                                                            
CONECT   59   60                                                            
CONECT   60   59   61   67                                                  
CONECT   61   60   62   73                                                  
CONECT   62   61                                                            
CONECT   63   64                                                            
CONECT   64   63   65                                                       
CONECT   65   64   66   73                                                  
CONECT   66   65   67                                                       
CONECT   67   60   66   68                                                  
CONECT   68   67   69                                                       
CONECT   69   54   68   70                                                  
CONECT   70   69   71   75                                                  
CONECT   71   56   70   72                                                  
CONECT   72   71                                                            
CONECT   73   61   65   74                                                  
CONECT   74   73                                                            
CONECT   75   70                                                            
MASTER        0    0    0    0    0    0    0    0   75    0  166    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₁H₈₆O₂₄

Average Mass

1083.2141 Da

Monoisotopic Mass

1082.55090 Da

IUPAC Name

2-({2-[(4,5-dihydroxy-6-{[6-hydroxy-7,9,13-trimethyl-6-(3-methyl-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butyl)-5-oxapentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosan-16-yl]oxy}-2-(hydroxymethyl)oxan-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

CAS Registry Number

75557-22-1

SMILES

CC(CCC1(O)OC2CC3C4CCC5CC(CCC5(C)C4CCC3(C)C2C1C)OC1OC(CO)C(OC2OC(CO)C(O)C(O)C2OC2OC(CO)C(O)C(O)C2O)C(O)C1O)COC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C51H86O24/c1-20(19-67-45-40(63)36(59)33(56)28(15-52)69-45)7-12-51(66)21(2)32-27(75-51)14-26-24-6-5-22-13-23(8-10-49(22,3)25(24)9-11-50(26,32)4)68-46-42(65)39(62)43(31(18-55)72-46)73-48-44(38(61)35(58)30(17-54)71-48)74-47-41(64)37(60)34(57)29(16-53)70-47/h20-48,52-66H,5-19H2,1-4H3

InChI Key

OFEAYOYKIQKFSK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Solanum lycopersicum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Tribulus terrestris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal saponins

Alternative Parents

Substituents

Steroidal saponin
Diterpene glycoside
Furostane-skeleton
Oligosaccharide
22-hydroxysteroid
Diterpenoid
Hydroxysteroid
Terpene glycoside
Fatty acyl glycoside
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Oxane
Fatty acyl
Tetrahydrofuran
Hemiacetal
Secondary alcohol
Oxacycle
Polyol
Organoheterocyclic compound
Acetal
Organooxygen compound
Hydrocarbon derivative
Primary alcohol
Organic oxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-0.88	ALOGPS
logP	-2.9	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.51	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	24	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	386.52 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	252.58 m³·mol⁻¹	ChemAxon
Polarizability	114.32 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

HMDB0034083

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012342

KNApSAcK ID

Not Available

Chemspider ID

376960

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

426059

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Tomatoside A (NP0047848)

MOL for NP0047848 (Tomatoside A)

3D MOL for NP0047848 (Tomatoside A)

3D SDF for NP0047848 (Tomatoside A)

3D-SDF for NP0047848 (Tomatoside A)

PDB for NP0047848 (Tomatoside A)

3D PDB for NP0047848 (Tomatoside A)

SMILES for NP0047848 (Tomatoside A)

INCHI for NP0047848 (Tomatoside A)

Structure for NP0047848 (Tomatoside A)

3D Structure for NP0047848 (Tomatoside A)