NP-MRD: Showing NP-Card for (1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside (NP0334929)

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Record Information

Version

2.0

Created at

2024-09-10 23:07:06 UTC

Updated at

2024-09-10 23:07:06 UTC

NP-MRD ID

NP0334929

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside

Description

(1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside 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. Based on a literature review very few articles have been published on (1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262301392D          

 25 26  0  0  0  0            999 V2000
   -2.5004    0.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004    0.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734    0.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734    0.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    1.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4784    1.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1876    1.8069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578    1.2385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0734   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -2.0629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578   -1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3577    0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3577    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720   -0.4127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7848    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7848    0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720   -1.2385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3564   -1.6513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004   -0.4127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004    1.2385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720    2.0629    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
  3 10  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 15  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  1  0  0  0  0
 12 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 20  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  1  0  0  0  0
 19 20  1  0  0  0  0
 19 24  1  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334929

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)(CO)C1CCC(C)(O)C(C1)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1/C16H30O9/c1-15(22)4-3-8(16(2,23)7-18)5-10(15)25-14-13(21)12(20)11(19)9(6-17)24-14/h8-14,17-23H,3-7H2,1-2H3

> <INCHI_KEY>
HKSOQIVAOUMKMF-UHFFFAOYNA-N

> <FORMULA>
C16H30O9

> <MOLECULAR_WEIGHT>
366.407

> <EXACT_MASS>
366.188982546

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.57761553549975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[5-(1,2-dihydroxypropan-2-yl)-2-hydroxy-2-methylcyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
-2.7059331853333344

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.082556258349193

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.194916308619913

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083554675248

> <JCHEM_POLAR_SURFACE_AREA>
160.07

> <JCHEM_REFRACTIVITY>
84.68949999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-{[5-(1,2-dihydroxypropan-2-yl)-2-hydroxy-2-methylcyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -4.667   1.544   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.667   0.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.334  -0.768   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.004   0.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.004   1.544   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.334   2.312   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.626   3.152   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.217   3.373   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -0.668   2.312   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.334  -2.309   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.004  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.334  -3.851   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.668  -2.309   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.668   1.541   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.668   0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.332   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.332   1.541   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.001   2.309   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.001  -2.312   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.665  -3.082   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.667  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.667   2.312   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.001   3.851   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    1    5    7    8                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   15                                                       
CONECT   10    3   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10   14                                                       
CONECT   13   10                                                            
CONECT   14   12                                                            
CONECT   15    9   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20   24                                                  
CONECT   20   15   19   25                                                  
CONECT   21   17   22                                                       
CONECT   22   21                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₃₀O₉

Average Mass

366.4070 Da

Monoisotopic Mass

366.18898 Da

IUPAC Name

2-{[5-(1,2-dihydroxypropan-2-yl)-2-hydroxy-2-methylcyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-{[5-(1,2-dihydroxypropan-2-yl)-2-hydroxy-2-methylcyclohexyl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CC(O)(CO)C1CCC(C)(O)C(C1)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1/C16H30O9/c1-15(22)4-3-8(16(2,23)7-18)5-10(15)25-14-13(21)12(20)11(19)9(6-17)24-14/h8-14,17-23H,3-7H2,1-2H3

InChI Key

HKSOQIVAOUMKMF-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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
Cyclohexanol
Monosaccharide
Oxane
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-2.7	ChemAxon
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	160.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	84.69 m³·mol⁻¹	ChemAxon
Polarizability	37.58 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside (NP0334929)

MOL for NP0334929 ((1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside)

3D MOL for NP0334929 ((1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside)

3D SDF for NP0334929 ((1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside)

3D-SDF for NP0334929 ((1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside)

PDB for NP0334929 ((1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside)

3D PDB for NP0334929 ((1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside)

SMILES for NP0334929 ((1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside)

INCHI for NP0334929 ((1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside)

Structure for NP0334929 ((1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside)

3D Structure for NP0334929 ((1S,2S,4R,8R)-p-Menthane-1,2,8,9-tetrol 2-glucoside)