NP-MRD: Showing NP-Card for (3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid (NP0236374)

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Record Information

Version

2.0

Created at

2022-09-06 19:15:41 UTC

Updated at

2022-09-06 19:15:41 UTC

NP-MRD ID

NP0236374

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid

Description

(3R)-3-[(3S,3aR,6S,6aR)-3,6-dihydroxy-2-oxo-3a-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydrofuro[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid 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. (3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid is found in Viburnum wrightii. Based on a literature review very few articles have been published on (3R)-3-[(3S,3aR,6S,6aR)-3,6-dihydroxy-2-oxo-3a-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydrofuro[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062221152D          

 35 38  0  0  1  0            999 V2000
   -0.8739   -2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309062221152D          

 35 38  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0236374

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](O[C@]23OC[C@H](O)[C@H]2OC(=O)[C@]3(O)[C@H](CC(O)=O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O14/c22-6-12-14(27)15(28)16(29)18(33-12)35-21-17(11(24)7-32-21)34-19(30)20(21,31)10(5-13(25)26)8-1-3-9(23)4-2-8/h1-4,10-12,14-18,22-24,27-29,31H,5-7H2,(H,25,26)/t10-,11+,12-,14-,15+,16-,17-,18+,20-,21-/m1/s1

> <INCHI_KEY>
PQTDFOIAAQSUKY-ZQEZFPCCSA-N

> <FORMULA>
C21H26O14

> <MOLECULAR_WEIGHT>
502.425

> <EXACT_MASS>
502.132255517

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
44.96748677629505

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-[(3S,3aR,6S,6aR)-3,6-dihydroxy-2-oxo-3a-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydrofuro[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid

> <JCHEM_LOGP>
-2.2692626426666673

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.43702265015715

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6503506212496433

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849158899915

> <JCHEM_POLAR_SURFACE_AREA>
232.89999999999995

> <JCHEM_REFRACTIVITY>
107.20050000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-[(3S,3aR,6S,6aR)-3,6-dihydroxy-2-oxo-3a-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5H-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0      -1.631  -4.032   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.631  -2.492   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.965  -1.722   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.298  -1.722   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.036  -2.492   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.036  -4.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.370  -4.802   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.370  -6.342   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.036  -7.112   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.036  -8.652   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.298  -6.342   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.298  -4.802   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.996  -3.129   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.075  -0.476   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.370   0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.299   0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.775   2.235   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.299  -1.722   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.834  -2.786   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.168  -3.556   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.168  -5.096   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.502  -5.866   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.502  -7.406   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.168  -8.176   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.835  -5.096   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.169  -5.866   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.835  -3.556   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.169  -2.786   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.502  -2.786   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.502  -1.246   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6                                                       
CONECT   13    5   14   15   23                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   13   24                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   25   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
(3R)-3-[(3S,3AR,6S,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydrofuro[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoate	Generator

Chemical Formula

C₂₁H₂₆O₁₄

Average Mass

502.4250 Da

Monoisotopic Mass

502.13226 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](O[C@]23OC[C@H](O)[C@H]2OC(=O)[C@]3(O)[C@H](CC(O)=O)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C21H26O14/c22-6-12-14(27)15(28)16(29)18(33-12)35-21-17(11(24)7-32-21)34-19(30)20(21,31)10(5-13(25)26)8-1-3-9(23)4-2-8/h1-4,10-12,14-18,22-24,27-29,31H,5-7H2,(H,25,26)/t10-,11+,12-,14-,15+,16-,17-,18+,20-,21-/m1/s1

InChI Key

PQTDFOIAAQSUKY-ZQEZFPCCSA-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
Viburnum wrightii	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
Disaccharide
Glycosyl compound
O-glycosyl compound
3-phenylpropanoic-acid
Isosorbide
Furofuran
1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Gamma butyrolactone
Oxane
Tertiary alcohol
Oxolane
Lactone
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Alcohol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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

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

8566783

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10391341

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid (NP0236374)

MOL for NP0236374 ((3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid)

3D MOL for NP0236374 ((3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid)

3D SDF for NP0236374 ((3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid)

3D-SDF for NP0236374 ((3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid)

PDB for NP0236374 ((3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid)

3D PDB for NP0236374 ((3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid)

SMILES for NP0236374 ((3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid)

INCHI for NP0236374 ((3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid)

Structure for NP0236374 ((3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid)

3D Structure for NP0236374 ((3r)-3-[(3s,3ar,6s,6ar)-3,6-dihydroxy-2-oxo-3a-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dihydro-5h-furo[3,2-b]furan-3-yl]-3-(4-hydroxyphenyl)propanoic acid)