NP-MRD: Showing NP-Card for Taraxacolide 1-O-b-D-glucopyranoside (NP0048271)

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Record Information

Version

2.0

Created at

2022-03-17 20:53:49 UTC

Updated at

2022-03-17 20:53:49 UTC

NP-MRD ID

NP0048271

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taraxacolide 1-O-b-D-glucopyranoside

Description

Taraxacolide 1-O-b-D-glucopyranoside belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Taraxacolide 1-O-b-D-glucopyranoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Taraxacolide 1-O-b-D-glucopyranoside has been detected, but not quantified in, several different foods, such as alcoholic beverages, beverages, coffee and coffee products, and tea. Taraxacolide 1-O-b-D-glucopyranoside is found in Taraxacum officinale. This could make taraxacolide 1-O-b-D-glucopyranoside a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308352D          

 30 33  0  0  0  0            999 V2000
    4.2295    1.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944   -1.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7591    1.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947    3.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1047    2.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5393    1.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1493    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247    1.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8901    1.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3193    3.3978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639    1.9696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5839    0.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613   -0.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801    2.6193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 10  1  0  0  0  0
 18 14  1  0  0  0  0
 19  8  1  0  0  0  0
 20 17  1  0  0  0  0
 21  3  1  0  0  0  0
 21  5  1  0  0  0  0
 21 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22  7  1  0  0  0  0
 23 11  2  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 19  2  0  0  0  0
 28 12  1  0  0  0  0
 28 20  1  0  0  0  0
 29 13  1  0  0  0  0
 29 20  1  0  0  0  0
 30 18  1  0  0  0  0
 30 19  1  0  0  0  0
M  END


  Mrv0541 05061308352D          

 30 33  0  0  0  0            999 V2000
    4.2295    1.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944   -1.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7591    1.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4947    3.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1047    2.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5393    1.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1493    1.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3247    1.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8901    1.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3193    3.3978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3639    1.9696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5839    0.5156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613   -0.3918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801    2.6193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655    1.8665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  8  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 14  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 10  1  0  0  0  0
 18 14  1  0  0  0  0
 19  8  1  0  0  0  0
 20 17  1  0  0  0  0
 21  3  1  0  0  0  0
 21  5  1  0  0  0  0
 21 13  1  0  0  0  0
 21 14  1  0  0  0  0
 22  7  1  0  0  0  0
 23 11  2  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 19  2  0  0  0  0
 28 12  1  0  0  0  0
 28 20  1  0  0  0  0
 29 13  1  0  0  0  0
 29 20  1  0  0  0  0
 30 18  1  0  0  0  0
 30 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048271

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2CCC3(C)C(CC(=O)C(C)C3C2OC1=O)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H32O9/c1-8-10-4-5-21(3)13(6-11(23)9(2)14(21)18(10)30-19(8)27)29-20-17(26)16(25)15(24)12(7-22)28-20/h8-10,12-18,20,22,24-26H,4-7H2,1-3H3

> <INCHI_KEY>
ZNBJBJUEJZNPLD-UHFFFAOYSA-N

> <FORMULA>
C21H32O9

> <MOLECULAR_WEIGHT>
428.4734

> <EXACT_MASS>
428.204632622

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
44.8578394589492

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5a,9-trimethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydronaphtho[1,2-b]furan-2,8-dione

> <ALOGPS_LOGP>
-0.36

> <JCHEM_LOGP>
-0.12706963733333354

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200068733741922

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210530307000356

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835454267677

> <JCHEM_POLAR_SURFACE_AREA>
142.75

> <JCHEM_REFRACTIVITY>
100.98159999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5a,9-trimethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3H-naphtho[1,2-b]furan-2,8-dione

> <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       7.895   2.610   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.790  -1.944   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.417   3.436   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.657   6.294   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.719   1.616   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.062  -0.587   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.929   4.937   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.740   3.628   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.012   2.271   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.473   2.223   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.662   3.532   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.196   6.343   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.289  -1.848   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -6.279   3.677   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -4.823   0.962   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.745   0.866   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.141  -0.731   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.390   4.889   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -0.122   3.484   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.406  -0.502   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   21                                                            
CONECT    4    5   10                                                       
CONECT    5    4   21                                                       
CONECT    6   11   13                                                       
CONECT    7   12   22                                                       
CONECT    8    1   10   19                                                  
CONECT    9    2   11   14                                                  
CONECT   10    4    8   18                                                  
CONECT   11    6    9   23                                                  
CONECT   12    7   15   28                                                  
CONECT   13    6   21   29                                                  
CONECT   14    9   18   21                                                  
CONECT   15   12   16   24                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   20   26                                                  
CONECT   18   10   14   30                                                  
CONECT   19    8   27   30                                                  
CONECT   20   17   28   29                                                  
CONECT   21    3    5   13   14                                             
CONECT   22    7                                                            
CONECT   23   11                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
CONECT   26   17                                                            
CONECT   27   19                                                            
CONECT   28   12   20                                                       
CONECT   29   13   20                                                       
CONECT   30   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₃₂O₉

Average Mass

428.4734 Da

Monoisotopic Mass

428.20463 Da

IUPAC Name

3,5a,9-trimethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydronaphtho[1,2-b]furan-2,8-dione

Traditional Name

3,5a,9-trimethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydro-3H-naphtho[1,2-b]furan-2,8-dione

CAS Registry Number

75911-12-5

SMILES

CC1C2CCC3(C)C(CC(=O)C(C)C3C2OC1=O)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C21H32O9/c1-8-10-4-5-21(3)13(6-11(23)9(2)14(21)18(10)30-19(8)27)29-20-17(26)16(25)15(24)12(7-22)28-20/h8-10,12-18,20,22,24-26H,4-7H2,1-3H3

InChI Key

ZNBJBJUEJZNPLD-UHFFFAOYSA-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 officinale	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Terpene glycoside
Sesquiterpenoid
Naphthofuran
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Gamma butyrolactone
Monosaccharide
Oxane
Tetrahydrofuran
Cyclic ketone
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Primary 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	-0.36	ALOGPS
logP	-0.13	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	142.75 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	100.98 m³·mol⁻¹	ChemAxon
Polarizability	44.86 Å³	ChemAxon
Number of Rings	4	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

HMDB0035610

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014312

KNApSAcK ID

Not Available

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

131751813

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Taraxacolide 1-O-b-D-glucopyranoside (NP0048271)

MOL for NP0048271 (Taraxacolide 1-O-b-D-glucopyranoside)

3D MOL for NP0048271 (Taraxacolide 1-O-b-D-glucopyranoside)

3D SDF for NP0048271 (Taraxacolide 1-O-b-D-glucopyranoside)

3D-SDF for NP0048271 (Taraxacolide 1-O-b-D-glucopyranoside)

PDB for NP0048271 (Taraxacolide 1-O-b-D-glucopyranoside)

3D PDB for NP0048271 (Taraxacolide 1-O-b-D-glucopyranoside)

SMILES for NP0048271 (Taraxacolide 1-O-b-D-glucopyranoside)

INCHI for NP0048271 (Taraxacolide 1-O-b-D-glucopyranoside)

Structure for NP0048271 (Taraxacolide 1-O-b-D-glucopyranoside)

3D Structure for NP0048271 (Taraxacolide 1-O-b-D-glucopyranoside)