NP-MRD: Showing NP-Card for 2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}oxane-3,4,5-triol (NP0212576)

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Record Information

Version

2.0

Created at

2022-09-05 11:16:55 UTC

Updated at

2022-09-05 11:16:56 UTC

NP-MRD ID

NP0212576

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

4-Megastigmene-6a,9R-diol 9-[apiosyl-(1->6)-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. 4-Megastigmene-6a,9R-diol 9-[apiosyl-(1->6)-glucoside] is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-Megastigmene-6a,9R-diol 9-[apiosyl-(1->6)-glucoside] has been detected, but not quantified in, fruits. 2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}oxane-3,4,5-triol is found in Cydonia oblonga. This could make 4-megastigmene-6a,9R-diol 9-[apiosyl-(1->6)-glucoside] a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652307201900082D          

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M  END

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M  END


  Mrv1652307201900082D          

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  6  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  1  0  0  0  0
 13  1  1  0  0  0  0
 13  6  2  0  0  0  0
 14  2  1  0  0  0  0
 14  7  1  0  0  0  0
 15 10  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
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22  3  1  0  0  0  0
 22  4  1  0  0  0  0
 22  8  1  0  0  0  0
 23 11  1  0  0  0  0
 23 12  1  0  0  0  0
 23 19  1  0  0  0  0
 24  9  1  0  0  0  0
 24 13  1  0  0  0  0
 24 22  1  0  0  0  0
 25 11  1  0  0  0  0
 26 16  1  0  0  0  0
 27 17  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  1  0  0  0  0
 30 23  1  0  0  0  0
 31 24  1  0  0  0  0
 32 10  1  0  0  0  0
 32 21  1  0  0  0  0
 33 12  1  0  0  0  0
 33 21  1  0  0  0  0
 34 14  1  0  0  0  0
 34 20  1  0  0  0  0
 35 15  1  0  0  0  0
 35 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0212576

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC1(O)C(C)=CCCC1(C)C)OC1OC(COC2OCC(O)(CO)C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H42O11/c1-13-6-5-8-22(3,4)24(13,31)9-7-14(2)34-20-18(28)17(27)16(26)15(35-20)10-32-21-19(29)23(30,11-25)12-33-21/h6,14-21,25-31H,5,7-12H2,1-4H3

> <INCHI_KEY>
QWCOEYNCDIXGMI-UHFFFAOYSA-N

> <FORMULA>
C24H42O11

> <MOLECULAR_WEIGHT>
506.589

> <EXACT_MASS>
506.272712172

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.392692288607336

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
-0.7587563550000007

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.308989373716454

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.702004984412419

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423790163389214

> <JCHEM_POLAR_SURFACE_AREA>
178.52999999999997

> <JCHEM_REFRACTIVITY>
122.58399999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}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      -3.033   6.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.507   5.248   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   6.160   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       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.805   6.786   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.004   4.308   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.990   4.980   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.744   6.786   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.527   7.607   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.774   5.642   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      16.329   8.251   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      10.669   9.240   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.002  10.780   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      15.064   8.293   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      17.020   4.737   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.990   4.980   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      13.498   4.628   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       8.002   6.160   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   14                                                            
CONECT    3   22                                                            
CONECT    4   22                                                            
CONECT    5    6    8                                                       
CONECT    6    5   13                                                       
CONECT    7    9   14                                                       
CONECT    8    5   22                                                       
CONECT    9    7   24                                                       
CONECT   10   15   32                                                       
CONECT   11   23   25                                                       
CONECT   12   23   33                                                       
CONECT   13    1    6   24                                                  
CONECT   14    2    7   34                                                  
CONECT   15   10   16   35                                                  
CONECT   16   15   17   26                                                  
CONECT   17   16   18   27                                                  
CONECT   18   17   20   28                                                  
CONECT   19   21   23   29                                                  
CONECT   20   18   34   35                                                  
CONECT   21   19   32   33                                                  
CONECT   22    3    4    8   24                                             
CONECT   23   11   12   19   30                                             
CONECT   24    9   13   22   31                                             
CONECT   25   11                                                            
CONECT   26   16                                                            
CONECT   27   17                                                            
CONECT   28   18                                                            
CONECT   29   19                                                            
CONECT   30   23                                                            
CONECT   31   24                                                            
CONECT   32   10   21                                                       
CONECT   33   12   21                                                       
CONECT   34   14   20                                                       
CONECT   35   15   20                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₄₂O₁₁

Average Mass

506.5890 Da

Monoisotopic Mass

506.27271 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(CCC1(O)C(C)=CCCC1(C)C)OC1OC(COC2OCC(O)(CO)C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C24H42O11/c1-13-6-5-8-22(3,4)24(13,31)9-7-14(2)34-20-18(28)17(27)16(26)15(35-20)10-32-21-19(29)23(30,11-25)12-33-21/h6,14-21,25-31H,5,7-12H2,1-4H3

InChI Key

QWCOEYNCDIXGMI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
Megastigmane sesquiterpenoid
Sesquiterpenoid
Alkyl glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
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	0.11	ALOGPS
logP	-0.76	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	11.7	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	178.53 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	122.58 m³·mol⁻¹	ChemAxon
Polarizability	53.39 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0041580

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021571

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

85227631

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}oxane-3,4,5-triol (NP0212576)

MOL for NP0212576 (2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}oxane-3,4,5-triol)

3D MOL for NP0212576 (2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}oxane-3,4,5-triol)

3D SDF for NP0212576 (2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}oxane-3,4,5-triol)

3D-SDF for NP0212576 (2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}oxane-3,4,5-triol)

PDB for NP0212576 (2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}oxane-3,4,5-triol)

3D PDB for NP0212576 (2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}oxane-3,4,5-triol)

SMILES for NP0212576 (2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}oxane-3,4,5-triol)

INCHI for NP0212576 (2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}oxane-3,4,5-triol)

Structure for NP0212576 (2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}oxane-3,4,5-triol)

3D Structure for NP0212576 (2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-{[4-(1-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)butan-2-yl]oxy}oxane-3,4,5-triol)