NP-MRD: Showing NP-Card for 1-Menthyl-beta-D-glucoside (NP0046832)

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Record Information

Version

2.0

Created at

2022-03-17 20:30:15 UTC

Updated at

2022-03-17 20:30:15 UTC

NP-MRD ID

NP0046832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-Menthyl-beta-D-glucoside

Description

Menthyl pyrrolidone carboxylate belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Menthyl pyrrolidone carboxylate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Menthyl pyrrolidone carboxylate has been detected, but not quantified in, peppermints. This could make menthyl pyrrolidone carboxylate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212462D          

 22 23  0  0  0  0            999 V2000
   -4.2321    1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5176    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5176    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2321    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9466    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9466    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2321    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2321   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9466   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5176   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5657    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7407    0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3281    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7406   -0.7145    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5656   -0.7145    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9781    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8031    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9782   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3281    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4969    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3281   -1.4290    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4969    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  1  0  0  0
  4  8  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  3 17  1  1  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 12 19  1  6  0  0  0
 14 13  1  0  0  0  0
 13 20  1  1  0  0  0
 14 15  1  0  0  0  0
 14 21  1  6  0  0  0
 15 16  1  0  0  0  0
 15 18  1  1  0  0  0
 16 17  1  6  0  0  0
 19 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046832

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H30O6/c1-8(2)10-5-4-9(3)6-11(10)21-16-15(20)14(19)13(18)12(7-17)22-16/h8-20H,4-7H2,1-3H3/t9-,10+,11-,12-,13-,14+,15-,16-/m1/s1

> <INCHI_KEY>
GZSDZJZIZBGBON-NZZARTGWSA-N

> <FORMULA>
C16H30O6

> <MOLECULAR_WEIGHT>
318.4058

> <EXACT_MASS>
318.204238692

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.44122795210587

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.47

> <JCHEM_LOGP>
0.8934375013333334

> <ALOGPS_LOGS>
-1.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200090355731682

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.21056213276569

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083542786302

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
79.8586

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-menthyl β-D-glucoside

> <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      -7.900   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.566   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.566   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.900   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.234   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.234   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.900   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.900  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.234  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.566  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.923   1.334   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.383   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.612   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.382  -1.334   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.922  -1.334   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.692   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.232   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -3.693  -2.667   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.612   2.667   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.928   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.612  -2.667   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.928   2.667   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    1                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   12   16                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   20                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   18                                                  
CONECT   16   11   15   17                                                  
CONECT   17    3   16                                                       
CONECT   18   15                                                            
CONECT   19   12   22                                                       
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
(-)-Menthyl O-beta-glucopyranoside	ChEBI
(-)-Menthyl O-beta-D-glucoside	ChEBI
(-)-Menthyl O-b-glucopyranoside	Generator
(-)-Menthyl O-β-glucopyranoside	Generator
(-)-Menthyl O-b-D-glucoside	Generator
(-)-Menthyl O-β-D-glucoside	Generator
Menthyl pyrrolidone carboxylic acid	Generator
(-)-Menthyl b-D-glucoside	Generator
(-)-Menthyl β-D-glucoside	Generator
1-Menthyl-b-D-glucoside	Generator
1-Menthyl-β-D-glucoside	Generator

Chemical Formula

C₁₆H₃₀O₆

Average Mass

318.4058 Da

Monoisotopic Mass

318.20424 Da

IUPAC Name

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy}oxane-3,4,5-triol

Traditional Name

(-)-menthyl β-D-glucoside

CAS Registry Number

52528-10-6

SMILES

CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C16H30O6/c1-8(2)10-5-4-9(3)6-11(10)21-16-15(20)14(19)13(18)12(7-17)22-16/h8-20H,4-7H2,1-3H3/t9-,10+,11-,12-,13-,14+,15-,16-/m1/s1

InChI Key

GZSDZJZIZBGBON-NZZARTGWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mentha x piperita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Glycosyl compound
O-glycosyl compound
Monocyclic monoterpenoid
Monoterpenoid
P-menthane monoterpenoid
Oxane
Monosaccharide
Secondary alcohol
Polyol
Acetal
Oxacycle
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:15411 )
Menthane monoterpenoids (C03962 )
Menthane monoterpenoids (LMPR0102090060 )

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	0.47	ALOGPS
logP	0.89	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.86 m³·mol⁻¹	ChemAxon
Polarizability	34.44 Å³	ChemAxon
Number of Rings	2	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

HMDB0032368

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB006135

KNApSAcK ID

Not Available

Chemspider ID

4573550

KEGG Compound ID

C03962

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5459767

PDB ID

Not Available

ChEBI ID

15411

Good Scents ID

Not Available

References

General References

Showing NP-Card for 1-Menthyl-beta-D-glucoside (NP0046832)

MOL for NP0046832 (1-Menthyl-beta-D-glucoside)

3D MOL for NP0046832 (1-Menthyl-beta-D-glucoside)

3D SDF for NP0046832 (1-Menthyl-beta-D-glucoside)

3D-SDF for NP0046832 (1-Menthyl-beta-D-glucoside)

PDB for NP0046832 (1-Menthyl-beta-D-glucoside)

3D PDB for NP0046832 (1-Menthyl-beta-D-glucoside)

SMILES for NP0046832 (1-Menthyl-beta-D-glucoside)

INCHI for NP0046832 (1-Menthyl-beta-D-glucoside)

Structure for NP0046832 (1-Menthyl-beta-D-glucoside)

3D Structure for NP0046832 (1-Menthyl-beta-D-glucoside)