NP-MRD: Showing NP-Card for (23R)-Acetoxytomatine (NP0047982)

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Record Information

Version

2.0

Created at

2022-03-17 20:49:07 UTC

Updated at

2022-03-17 20:49:07 UTC

NP-MRD ID

NP0047982

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(23R)-Acetoxytomatine

Description

(23R)-Acetoxytomatine, also known as lycoperoside 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 (23R)-Acetoxytomatine is a very strong basic compound (based on its pKa). Outside of the human body, (23R)-acetoxytomatine has been detected, but not quantified in, garden tomato and garden tomato (var.). (23R)-Acetoxytomatine is found in Solanum lycopersicum Miller . This could make (23R)-acetoxytomatine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241208452D          

 76 85  0  0  0  0            999 V2000
    6.1026    1.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4892    0.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2466   -0.0475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7199    0.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7862    0.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4324    1.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241208452D          

 76 85  0  0  0  0            999 V2000
    6.1026    1.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4892    0.7132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3804   -2.4663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  7  8  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0047982

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3C4CCC5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(CO)C(O)C(OC4OCC(O)C(O)C4O)C3OC3OC(CO)C(O)C(O)C3O)C(O)C2O)OC11NCC(C)CC1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C52H85NO23/c1-20-12-33(68-22(3)57)52(53-15-20)21(2)34-29(76-52)14-27-25-7-6-23-13-24(8-10-50(23,4)26(25)9-11-51(27,34)5)69-47-42(66)39(63)43(32(18-56)72-47)73-49-45(75-48-41(65)38(62)36(60)30(16-54)70-48)44(37(61)31(17-55)71-49)74-46-40(64)35(59)28(58)19-67-46/h20-21,23-49,53-56,58-66H,6-19H2,1-5H3

> <INCHI_KEY>
POWISKNFFRUCCW-UHFFFAOYSA-N

> <FORMULA>
C52H85NO23

> <MOLECULAR_WEIGHT>
1092.2242

> <EXACT_MASS>
1091.551238031

> <JCHEM_ACCEPTOR_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
115.26509755064394

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-[(3,4-dihydroxy-5-{[5-hydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-2-yl)oxy]-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]-3'-yl acetate

> <ALOGPS_LOGP>
-0.21

> <JCHEM_LOGP>
-1.8426273426666635

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
10

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.225606673612928

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.777827276021654

> <JCHEM_PKA_STRONGEST_BASIC>
8.540273338351266

> <JCHEM_POLAR_SURFACE_AREA>
364.16

> <JCHEM_REFRACTIVITY>
255.1901000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-[(3,4-dihydroxy-5-{[5-hydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-2-yl)oxy]-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]-3'-yl acetate

> <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                                  
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HETATM    2  C   UNK     0      10.247   1.331   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.452   2.605   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.794  -0.089   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      11.214  -0.541   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      12.544   0.058   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.668   1.488   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.874   2.154   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       9.470  -1.573   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.209  -2.044   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.121  -3.106   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.845  -2.399   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.571  -3.194   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.571  -4.696   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.112  -5.223   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.839  -4.516   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.635  -5.182   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.710  -4.604   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.988  -5.399   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.787  -3.227   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.550  -2.630   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.965  -3.086   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.510  -1.496   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.295  -2.486   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.421  -1.056   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.625  -0.392   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.973  -0.971   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.097   0.459   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.414  -0.771   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.435   0.163   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.980   1.751   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.177   3.966   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.359   5.275   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      11.720   4.019   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -3.079  -4.308   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.678  -2.821   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.766  -1.730   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.258  -2.129   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -5.660  -3.621   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -4.568  -4.717   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -1.186  -2.425   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -6.349  -1.035   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -3.365  -0.240   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -6.058  -5.113   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -7.602  -5.113   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -5.950   0.457   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -4.453   0.837   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -4.036   2.324   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -5.117   3.428   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -6.614   3.045   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -7.031   1.555   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -8.525   1.169   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -7.695   4.148   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      -4.700   4.915   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -2.542   2.708   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -1.461   1.604   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -8.924  -0.323   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -9.238   4.148   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0     -10.010   5.486   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0     -11.556   5.486   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0     -12.330   4.148   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0     -11.556   2.808   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0     -10.010   2.808   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0     -10.411  -0.727   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0     -10.807  -2.216   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      -9.716  -3.305   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      -8.230  -2.903   0.000  0.00  0.00           C+0
HETATM   68  O   UNK     0      -7.836  -1.416   0.000  0.00  0.00           O+0
HETATM   69  O   UNK     0     -11.504   0.361   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0     -12.297  -2.617   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0     -10.113  -4.797   0.000  0.00  0.00           O+0
HETATM   72  C   UNK     0      -8.628  -4.395   0.000  0.00  0.00           C+0
HETATM   73  O   UNK     0      -9.719  -5.486   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      -9.238   1.473   0.000  0.00  0.00           O+0
HETATM   75  O   UNK     0     -12.328   1.470   0.000  0.00  0.00           O+0
HETATM   76  O   UNK     0     -13.874   4.148   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2   32                                                       
CONECT    4    2    5    9   30                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    1    6    8                                                  
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   29                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   27                                                  
CONECT   13   12   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   35                                                       
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   16   21   23   24                                             
CONECT   23   22                                                            
CONECT   24   13   22   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   12   26   28   29                                             
CONECT   28   27                                                            
CONECT   29   10   27   30                                                  
CONECT   30    4   29   31                                                  
CONECT   31   30                                                            
CONECT   32    3   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   19   36   40                                                  
CONECT   36   35   37   41                                                  
CONECT   37   36   38   43                                                  
CONECT   38   37   39   42                                                  
CONECT   39   38   40   44                                                  
CONECT   40   35   39                                                       
CONECT   41   36                                                            
CONECT   42   38   46                                                       
CONECT   43   37                                                            
CONECT   44   39   45                                                       
CONECT   45   44                                                            
CONECT   46   42   47   51                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   55                                                  
CONECT   49   48   50   54                                                  
CONECT   50   49   51   53                                                  
CONECT   51   46   50   52                                                  
CONECT   52   51   57                                                       
CONECT   53   50   58                                                       
CONECT   54   49                                                            
CONECT   55   48   56                                                       
CONECT   56   55                                                            
CONECT   57   52   64   68                                                  
CONECT   58   53   59   63                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62   76                                                  
CONECT   62   61   63   75                                                  
CONECT   63   58   62   74                                                  
CONECT   64   57   65   69                                                  
CONECT   65   64   66   70                                                  
CONECT   66   65   67   71                                                  
CONECT   67   66   68   72                                                  
CONECT   68   57   67                                                       
CONECT   69   64                                                            
CONECT   70   65                                                            
CONECT   71   66                                                            
CONECT   72   67   73                                                       
CONECT   73   72                                                            
CONECT   74   63                                                            
CONECT   75   62                                                            
CONECT   76   61                                                            
MASTER        0    0    0    0    0    0    0    0   76    0  170    0
END

View in JSmol

Synonyms

Value	Source
(23R)-23-Acetoxytomatidine	HMDB
23R-Acetoxytomatine	HMDB
Lycoperoside a	HMDB
16-[(3,4-Dihydroxy-5-{[5-hydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-2-yl)oxy]-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]-3'-yl acetic acid	Generator

Chemical Formula

C₅₂H₈₅NO₂₃

Average Mass

1092.2242 Da

Monoisotopic Mass

1091.55124 Da

IUPAC Name

16-[(3,4-dihydroxy-5-{[5-hydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}-6-(hydroxymethyl)oxan-2-yl)oxy]-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidine]-3'-yl acetate

Traditional Name

CAS Registry Number

176181-33-2

SMILES

CC1C2C(CC3C4CCC5CC(CCC5(C)C4CCC23C)OC2OC(CO)C(OC3OC(CO)C(O)C(OC4OCC(O)C(O)C4O)C3OC3OC(CO)C(O)C(O)C3O)C(O)C2O)OC11NCC(C)CC1OC(C)=O

InChI Identifier

InChI=1S/C52H85NO23/c1-20-12-33(68-22(3)57)52(53-15-20)21(2)34-29(76-52)14-27-25-7-6-23-13-24(8-10-50(23,4)26(25)9-11-51(27,34)5)69-47-42(66)39(63)43(32(18-56)72-47)73-49-45(75-48-41(65)38(62)36(60)30(16-54)70-48)44(37(61)31(17-55)71-49)74-46-40(64)35(59)28(58)19-67-46/h20-21,23-49,53-56,58-66H,6-19H2,1-5H3

InChI Key

POWISKNFFRUCCW-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...
Solanum lycopersicum Miller	Plant	KNApSAcK
Solanum lycopersicum var. lycopersicum	FooDB	KNAPSACK

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

Not Available

Substituents

Not Available

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	-0.21	ALOGPS
logP	-1.8	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.78	ChemAxon
pKa (Strongest Basic)	8.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	23	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	364.16 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	255.19 m³·mol⁻¹	ChemAxon
Polarizability	115.27 Å³	ChemAxon
Number of Rings	10	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

HMDB0034485

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013272

KNApSAcK ID

C00028514

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

131751568

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (23R)-Acetoxytomatine (NP0047982)

MOL for NP0047982 ((23R)-Acetoxytomatine)

3D MOL for NP0047982 ((23R)-Acetoxytomatine)

3D SDF for NP0047982 ((23R)-Acetoxytomatine)

3D-SDF for NP0047982 ((23R)-Acetoxytomatine)

PDB for NP0047982 ((23R)-Acetoxytomatine)

3D PDB for NP0047982 ((23R)-Acetoxytomatine)

SMILES for NP0047982 ((23R)-Acetoxytomatine)

INCHI for NP0047982 ((23R)-Acetoxytomatine)

Structure for NP0047982 ((23R)-Acetoxytomatine)

3D Structure for NP0047982 ((23R)-Acetoxytomatine)