NP-MRD: Showing NP-Card for 2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside (NP0074925)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 20:13:38 UTC

Updated at

2022-04-28 20:13:38 UTC

NP-MRD ID

NP0074925

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside

Description

(2R)-2,5-dimethyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydrofuran-3-one belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. 2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside is found in Passiflora quadrangularis . Based on a literature review very few articles have been published on (2R)-2,5-dimethyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydrofuran-3-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    2.5335   -0.0022   -2.3553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314    0.1545   -0.8923 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9107   -0.3393    0.0461 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7716   -1.0598   -0.2301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4611   -0.4183   -0.5945 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9106    0.4334    0.3952 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2107    0.8013    0.0774 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5977    2.1298    0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5238    2.1437    2.0506 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1116   -0.3141    0.4883 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4210    0.0458    0.1805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6697   -1.5572   -0.2103 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5184   -2.6215    0.6961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4687   -1.3942   -1.0774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8627   -1.1293   -2.4111 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4477    0.0264    1.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9240   -0.2503    2.4526 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6997    0.7690    1.1096 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9207    0.0009    1.5960 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7823    0.8265   -0.3070 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5099   -0.1915   -2.8523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8441   -0.8138   -2.6112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1285    0.9307   -2.7883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1807    0.2399   -1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2658    0.9059   -1.0233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6301    2.3474    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8728    2.8806    0.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1767    2.8146    2.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0680   -0.5005    1.5899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0036    0.0146    0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5224   -1.8758   -0.8809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9216   -3.3078    0.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9659   -2.4006   -1.1371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1729   -0.5606   -2.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7174    1.7693    1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1598   -0.8350    0.8892 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7035   -0.3758    2.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7517    0.7135    1.6417 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  1  0
 20  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  2  0
 16 18  1  0
 14  5  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
 18 35  1  1
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  6
  7 25  1  6
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  1
 11 30  1  0
 12 31  1  6
 13 32  1  0
 14 33  1  6
 15 34  1  0
M  END


  Mrv1652304282222132D          

 20 21  0  0  1  0            999 V2000
   -0.1067    5.5902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6078    6.0027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3222    5.5902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3222    4.7652    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6078    4.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1067    4.7652    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8212    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356    4.7652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    4.3527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242    2.2581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492    2.2581    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7041    3.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888    3.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9341    1.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846    3.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6078    6.8277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  4  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 13 16  1  1  0  0  0
 11 17  1  0  0  0  0
  3 18  1  1  0  0  0
  2 19  1  6  0  0  0
  1 20  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0074925

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1OC(C)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O8/c1-4-7(14)11(5(2)18-4)20-12-10(17)9(16)8(15)6(3-13)19-12/h4,6,8-10,12-13,15-17H,3H2,1-2H3/t4-,6-,8-,9+,10-,12+/m1/s1

> <INCHI_KEY>
ZCBCXLRKTUDKOP-IGIPTLBWSA-N

> <FORMULA>
C12H18O8

> <MOLECULAR_WEIGHT>
290.268

> <EXACT_MASS>
290.10016754

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.594103629655624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2,5-dimethyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydrofuran-3-one

> <ALOGPS_LOGP>
-1.22

> <JCHEM_LOGP>
-2.0923720660000003

> <ALOGPS_LOGS>
-0.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20339446872788

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.139766162964541

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092368361397

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
65.706

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2,5-dimethyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-furan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.199  10.435   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.134  11.205   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.468  10.435   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.468   8.895   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.134   8.125   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.199   8.895   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.533   8.125   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.867   8.895   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.802   8.125   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.802   6.585   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.556   5.680   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.032   4.215   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.572   4.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.048   5.680   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.512   6.156   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.477   2.969   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.091   6.156   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.802  11.205   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.134  12.745   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.533  11.205   0.000  0.00  0.00           O+0
CONECT    1    2    6   20                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   10   15                                                  
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17   11                                                            
CONECT   18    3                                                            
CONECT   19    2                                                            
CONECT   20    1                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₈O₈

Average Mass

290.2680 Da

Monoisotopic Mass

290.10017 Da

IUPAC Name

(2R)-2,5-dimethyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydrofuran-3-one

Traditional Name

(2R)-2,5-dimethyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-furan-3-one

CAS Registry Number

Not Available

SMILES

C[C@H]1OC(C)=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C1=O

InChI Identifier

InChI=1S/C12H18O8/c1-4-7(14)11(5(2)18-4)20-12-10(17)9(16)8(15)6(3-13)19-12/h4,6,8-10,12-13,15-17H,3H2,1-2H3/t4-,6-,8-,9+,10-,12+/m1/s1

InChI Key

ZCBCXLRKTUDKOP-IGIPTLBWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Passiflora quadrangularis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
3-furanone
Monosaccharide
Oxane
Dihydrofuran
Vinylogous ester
Cyclic ketone
Secondary alcohol
Ketone
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxide
Carbonyl group
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	-1.2	ALOGPS
logP	-2.1	ChemAxon
logS	-0.38	ALOGPS
pKa (Strongest Acidic)	10.14	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	65.71 m³·mol⁻¹	ChemAxon
Polarizability	27.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

163060860

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside (NP0074925)

MOL for NP0074925 (2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside)

3D MOL for NP0074925 (2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside)

3D SDF for NP0074925 (2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside)

3D-SDF for NP0074925 (2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside)

PDB for NP0074925 (2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside)

3D PDB for NP0074925 (2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside)

SMILES for NP0074925 (2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside)

INCHI for NP0074925 (2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside)

Structure for NP0074925 (2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside)

3D Structure for NP0074925 (2,5-Dimethyl-4-hydroxy-3(2H)-furanone beta-D-glucopyranoside)