NP-MRD: Showing NP-Card for 2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0247650)

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Record Information

Version

2.0

Created at

2022-09-07 09:34:34 UTC

Updated at

2022-09-07 09:34:34 UTC

NP-MRD ID

NP0247650

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

7,8-Dihydro-3b,6a-dihydroxy-alpha-ionol 9-glucoside belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. 7,8-Dihydro-3b,6a-dihydroxy-alpha-ionol 9-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 7,8-Dihydro-3b,6a-dihydroxy-alpha-ionol 9-glucoside has been detected, but not quantified in, fruits. 2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Cydonia oblonga. This could make 7,8-dihydro-3b,6a-dihydroxy-alpha-ionol 9-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307201900082D          

 27 28  0  0  0  0            999 V2000
   -0.2481    1.8928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    4.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    4.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428    2.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946    4.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    2.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249    3.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    4.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4374    3.7298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    2.6680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 10  1  1  0  0  0  0
 10  7  2  0  0  0  0
 11  2  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18  3  1  0  0  0  0
 18  4  1  0  0  0  0
 18  8  1  0  0  0  0
 19  6  1  0  0  0  0
 19 10  1  0  0  0  0
 19 18  1  0  0  0  0
 20  9  1  0  0  0  0
 21 12  1  0  0  0  0
 22 14  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 25 19  1  0  0  0  0
 26 11  1  0  0  0  0
 26 17  1  0  0  0  0
 27 13  1  0  0  0  0
 27 17  1  0  0  0  0
M  END


  Mrv1652307201900082D          

 27 28  0  0  0  0            999 V2000
   -0.2481    1.8928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    4.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    4.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3428    2.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0946    4.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303    2.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249    3.5865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    4.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4374    3.7298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303    2.6680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 10  1  1  0  0  0  0
 10  7  2  0  0  0  0
 11  2  1  0  0  0  0
 11  5  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18  3  1  0  0  0  0
 18  4  1  0  0  0  0
 18  8  1  0  0  0  0
 19  6  1  0  0  0  0
 19 10  1  0  0  0  0
 19 18  1  0  0  0  0
 20  9  1  0  0  0  0
 21 12  1  0  0  0  0
 22 14  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 25 19  1  0  0  0  0
 26 11  1  0  0  0  0
 26 17  1  0  0  0  0
 27 13  1  0  0  0  0
 27 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247650

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC1(O)C(C)=CC(O)CC1(C)C)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H34O8/c1-10-7-12(21)8-18(3,4)19(10,25)6-5-11(2)26-17-16(24)15(23)14(22)13(9-20)27-17/h7,11-17,20-25H,5-6,8-9H2,1-4H3

> <INCHI_KEY>
PKDTXFWHZWYNAH-UHFFFAOYSA-N

> <FORMULA>
C19H34O8

> <MOLECULAR_WEIGHT>
390.473

> <EXACT_MASS>
390.225368055

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
41.52910796702173

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.79

> <JCHEM_LOGP>
-0.7130683619999999

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.113990095857034

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.199605374544877

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8625803406741666

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
97.42930000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUL-19         0                                  
HETATM    1  C   UNK     0      -0.463   3.533   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.527   9.147   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.990   7.875   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.507   5.248   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.043   7.875   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.990   4.980   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.033   6.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.527   7.607   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.550   6.962   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.669   9.240   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002  10.780   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.990   4.980   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   18                                                            
CONECT    4   18                                                            
CONECT    5    6   11                                                       
CONECT    6    5   19                                                       
CONECT    7   10   12                                                       
CONECT    8   12   18                                                       
CONECT    9   13   20                                                       
CONECT   10    1    7   19                                                  
CONECT   11    2    5   26                                                  
CONECT   12    7    8   21                                                  
CONECT   13    9   14   27                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   26   27                                                  
CONECT   18    3    4    8   19                                             
CONECT   19    6   10   18   25                                             
CONECT   20    9                                                            
CONECT   21   12                                                            
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   16                                                            
CONECT   25   19                                                            
CONECT   26   11   17                                                       
CONECT   27   13   17                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
7,8-Dihydro-3b,6a-dihydroxy-a-ionol 9-glucoside	Generator
7,8-Dihydro-3b,6a-dihydroxy-α-ionol 9-glucoside	Generator

Chemical Formula

C₁₉H₃₄O₈

Average Mass

390.4730 Da

Monoisotopic Mass

390.22537 Da

IUPAC Name

2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CC(CCC1(O)C(C)=CC(O)CC1(C)C)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C19H34O8/c1-10-7-12(21)8-18(3,4)19(10,25)6-5-11(2)26-17-16(24)15(23)14(22)13(9-20)27-17/h7,11-17,20-25H,5-6,8-9H2,1-4H3

InChI Key

PKDTXFWHZWYNAH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cydonia oblonga	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Sesquiterpenoid
Megastigmane sesquiterpenoid
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Tertiary alcohol
Secondary alcohol
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
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	-0.79	ALOGPS
logP	-0.71	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	139.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	97.43 m³·mol⁻¹	ChemAxon
Polarizability	41.53 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

HMDB0041578

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021569

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

85161713

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0247650)

MOL for NP0247650 (2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0247650 (2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0247650 (2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0247650 (2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0247650 (2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0247650 (2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0247650 (2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0247650 (2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0247650 (2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0247650 (2-{[4-(1,4-dihydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)