NP-MRD: Showing NP-Card for Taraxinic acid glucosyl ester (NP0048190)

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Record Information

Version

2.0

Created at

2022-03-17 20:52:34 UTC

Updated at

2022-03-17 20:52:34 UTC

NP-MRD ID

NP0048190

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taraxinic acid glucosyl ester

Description

Taraxinic acid glucosyl ester belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Taraxinic acid glucosyl ester is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Taraxinic acid glucosyl ester has been detected, but not quantified in, several different foods, such as alcoholic beverages, beverages, coffee and coffee products, dandelions, and tea. Taraxinic acid glucosyl ester is found in Taraxacum disseminatum, Taraxacum erythrospermum, Taraxacum laevigatum and Taraxacum linearisquameum. This could make taraxinic acid glucosyl ester a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308192D          

 30 32  0  0  0  0            999 V2000
    5.0298    3.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558   -0.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124    1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037    0.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    1.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0233   -3.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614    1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5461   -2.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3602   -2.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8830   -2.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5917   -1.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279    1.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6722   -0.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7776   -1.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3146   -4.1992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6515   -3.6946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6971   -2.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1145   -0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1494   -1.1117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460    2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2548   -2.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4863   -0.6072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
 10  1  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  2  2  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 18  1  0  0  0  0
 26 19  2  0  0  0  0
 27 20  2  0  0  0  0
 28 14  1  0  0  0  0
 28 19  1  0  0  0  0
 29 15  1  0  0  0  0
 29 21  1  0  0  0  0
 30 20  1  0  0  0  0
 30 21  1  0  0  0  0
M  END


  Mrv0541 05061308192D          

 30 32  0  0  0  0            999 V2000
    5.0298    3.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8558   -0.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124    1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037    0.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    1.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0233   -3.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614    1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5461   -2.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3602   -2.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8830   -2.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5917   -1.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279    1.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6722   -0.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7776   -1.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3146   -4.1992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6515   -3.6946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6971   -2.4182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1145   -0.8745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1494   -1.1117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460    2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2548   -2.0172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4863   -0.6072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
 10  1  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  2  2  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 18  1  0  0  0  0
 22  9  1  0  0  0  0
 23 16  1  0  0  0  0
 24 17  1  0  0  0  0
 25 18  1  0  0  0  0
 26 19  2  0  0  0  0
 27 20  2  0  0  0  0
 28 14  1  0  0  0  0
 28 19  1  0  0  0  0
 29 15  1  0  0  0  0
 29 21  1  0  0  0  0
 30 20  1  0  0  0  0
 30 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048190

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(=O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O9/c1-10-4-3-5-12(6-7-13-11(2)19(26)28-14(13)8-10)20(27)30-21-18(25)17(24)16(23)15(9-22)29-21/h5,8,13-18,21-25H,2-4,6-7,9H2,1H3/b10-8-,12-5+

> <INCHI_KEY>
SIOXYUXOHTZOOM-INAGUISBSA-N

> <FORMULA>
C21H28O9

> <MOLECULAR_WEIGHT>
424.4416

> <EXACT_MASS>
424.173332494

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
43.24060069671402

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
0.9731244856666676

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.194438902169743

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.195723010853209

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810938228982016

> <JCHEM_POLAR_SURFACE_AREA>
142.75

> <JCHEM_REFRACTIVITY>
104.09479999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.389   6.071   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.331  -0.004   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.476   3.189   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.957   3.438   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.020   1.748   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.525   0.806   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.981   2.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.893   5.129   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.243  -6.398   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.413   4.879   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.259   1.534   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.044   0.557   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.461   2.497   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.918   3.937   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.219  -5.206   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.739  -5.456   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.715  -4.264   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.171  -2.824   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.972   2.380   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.588  -0.884   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.652  -2.574   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.787  -7.839   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      14.283  -6.897   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      16.235  -4.514   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      15.147  -1.632   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.531   1.836   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       9.612  -2.075   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.379   3.865   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      11.676  -3.765   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      12.108  -1.133   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3    4    5                                                       
CONECT    4    3   10                                                       
CONECT    5    3   12                                                       
CONECT    6    7   12                                                       
CONECT    7    6   13                                                       
CONECT    8   10   14                                                       
CONECT    9   15   22                                                       
CONECT   10    1    4    8                                                  
CONECT   11    2   13   19                                                  
CONECT   12    5    6   20                                                  
CONECT   13    7   11   14                                                  
CONECT   14    8   13   28                                                  
CONECT   15    9   16   29                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   24                                                  
CONECT   18   17   21   25                                                  
CONECT   19   11   26   28                                                  
CONECT   20   12   27   30                                                  
CONECT   21   18   29   30                                                  
CONECT   22    9                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25   18                                                            
CONECT   26   19                                                            
CONECT   27   20                                                            
CONECT   28   14   19                                                       
CONECT   29   15   21                                                       
CONECT   30   20   21                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
Taraxinate glucosyl ester	Generator
(-)-Taraxinic acid beta-glucopyranosyl ester	HMDB
Taraxinic acid beta-glucopyranosyl ester	HMDB
3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-methyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-6-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₈O₉

Average Mass

424.4416 Da

Monoisotopic Mass

424.17333 Da

IUPAC Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

Traditional Name

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylate

CAS Registry Number

75911-14-7

SMILES

C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C21H28O9/c1-10-4-3-5-12(6-7-13-11(2)19(26)28-14(13)8-10)20(27)30-21-18(25)17(24)16(23)15(9-22)29-21/h5,8,13-18,21-25H,2-4,6-7,9H2,1H3/b10-8-,12-5+

InChI Key

SIOXYUXOHTZOOM-INAGUISBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Taraxacum disseminatum	Plant	KNApSAcK
Taraxacum erythrospermum	LOTUS Database	35616633
Taraxacum laevigatum	Plant	KNApSAcK
Taraxacum linearisquameum	Plant	KNApSAcK
Taraxacum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Terpene glycoside
Germacrane sesquiterpenoid
Sesquiterpenoid
Hexose monosaccharide
Dicarboxylic acid or derivatives
Gamma butyrolactone
Monosaccharide
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Primary alcohol
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	-0.02	ALOGPS
logP	0.97	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	104.09 m³·mol⁻¹	ChemAxon
Polarizability	43.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035249

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013909

KNApSAcK ID

C00037887

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

131751687

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Taraxinic acid glucosyl ester (NP0048190)

MOL for NP0048190 (Taraxinic acid glucosyl ester)

3D MOL for NP0048190 (Taraxinic acid glucosyl ester)

3D SDF for NP0048190 (Taraxinic acid glucosyl ester)

3D-SDF for NP0048190 (Taraxinic acid glucosyl ester)

PDB for NP0048190 (Taraxinic acid glucosyl ester)

3D PDB for NP0048190 (Taraxinic acid glucosyl ester)

SMILES for NP0048190 (Taraxinic acid glucosyl ester)

INCHI for NP0048190 (Taraxinic acid glucosyl ester)

Structure for NP0048190 (Taraxinic acid glucosyl ester)

3D Structure for NP0048190 (Taraxinic acid glucosyl ester)