NP-MRD: Showing NP-Card for 4-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone (NP0059641)

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Record Information

Version

2.0

Created at

2022-04-28 04:51:52 UTC

Updated at

2022-04-28 04:51:52 UTC

NP-MRD ID

NP0059641

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone

Description

[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(4R)-4-methyl-6-[(2R,3R)-4-methylidene-5-oxo-2-(2-oxopropyl)oxolan-3-yl]-5-oxohexyl]oxy}oxan-2-yl]methyl acetate 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-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone is found in Picradeniopsis woodhousei. Based on a literature review very few articles have been published on [(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(4R)-4-methyl-6-[(2R,3R)-4-methylidene-5-oxo-2-(2-oxopropyl)oxolan-3-yl]-5-oxohexyl]oxy}oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282206512D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282206512D          

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M  END
> <DATABASE_ID>
NP0059641

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H](CCCO[C@@H]1O[C@@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O)C(=O)C[C@H]1[C@@H](CC(C)=O)OC(=O)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O11/c1-11(16(26)9-15-13(3)22(30)33-17(15)8-12(2)24)6-5-7-31-23-21(29)20(28)19(27)18(34-23)10-32-14(4)25/h11,15,17-21,23,27-29H,3,5-10H2,1-2,4H3/t11-,15-,17-,18+,19-,20+,21-,23-/m1/s1

> <INCHI_KEY>
VPXNYABMLVFZMO-RSYPBGBYSA-N

> <FORMULA>
C23H34O11

> <MOLECULAR_WEIGHT>
486.514

> <EXACT_MASS>
486.210111915

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
49.65582420297632

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(4R)-4-methyl-6-[(2R,3R)-4-methylidene-5-oxo-2-(2-oxopropyl)oxolan-3-yl]-5-oxohexyl]oxy}oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
-0.01

> <JCHEM_LOGP>
0.12377677800000018

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.214959823709254

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.212592294938494

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649084765163707

> <JCHEM_POLAR_SURFACE_AREA>
165.89000000000001

> <JCHEM_REFRACTIVITY>
114.87729999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(4R)-4-methyl-6-[(2R,3R)-4-methylidene-5-oxo-2-(2-oxopropyl)oxolan-3-yl]-5-oxohexyl]oxy}oxan-2-yl]methyl acetate

> <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  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.076  -2.454   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.396  -0.947   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.107  -3.598   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      14.638  -3.437   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      12.337  -4.932   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.830  -4.612   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.686  -5.642   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.006  -7.148   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.862  -8.179   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.471  -7.624   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2   21                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21    1   22   26                                                  
CONECT   22   21   23   34                                                  
CONECT   23   22   24   33                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25   21                                                       
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   24                                                            
CONECT   33   23                                                            
CONECT   34   22                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Value	Source
[(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-{[(4R)-4-methyl-6-[(2R,3R)-4-methylidene-5-oxo-2-(2-oxopropyl)oxolan-3-yl]-5-oxohexyl]oxy}oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₃H₃₄O₁₁

Average Mass

486.5140 Da

Monoisotopic Mass

486.21011 Da

IUPAC Name

[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(4R)-4-methyl-6-[(2R,3R)-4-methylidene-5-oxo-2-(2-oxopropyl)oxolan-3-yl]-5-oxohexyl]oxy}oxan-2-yl]methyl acetate

Traditional Name

[(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(4R)-4-methyl-6-[(2R,3R)-4-methylidene-5-oxo-2-(2-oxopropyl)oxolan-3-yl]-5-oxohexyl]oxy}oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

C[C@H](CCCO[C@@H]1O[C@@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]1O)C(=O)C[C@H]1[C@@H](CC(C)=O)OC(=O)C1=C

InChI Identifier

InChI=1S/C23H34O11/c1-11(16(26)9-15-13(3)22(30)33-17(15)8-12(2)24)6-5-7-31-23-21(29)20(28)19(27)18(34-23)10-32-14(4)25/h11,15,17-21,23,27-29H,3,5-10H2,1-2,4H3/t11-,15-,17-,18+,19-,20+,21-,23-/m1/s1

InChI Key

VPXNYABMLVFZMO-RSYPBGBYSA-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
Picradeniopsis woodhousei	Plant	KNApSAcK

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
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Oxane
Monosaccharide
Gamma butyrolactone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	-0.01	ALOGPS
logP	0.12	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	165.89 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	114.88 m³·mol⁻¹	ChemAxon
Polarizability	49.66 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

162998570

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 4-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone (NP0059641)

MOL for NP0059641 (4-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone)

3D MOL for NP0059641 (4-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone)

3D SDF for NP0059641 (4-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone)

3D-SDF for NP0059641 (4-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone)

PDB for NP0059641 (4-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone)

3D PDB for NP0059641 (4-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone)

SMILES for NP0059641 (4-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone)

INCHI for NP0059641 (4-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone)

Structure for NP0059641 (4-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone)

3D Structure for NP0059641 (4-[6-[(6-O-Acetyl-beta-D-glucopyranosyl)oxy]-3-methyl-2-oxohexyl]dihydro-3-methylene-5-(2-oxopropyl)-2(3H)-furanone)