NP-MRD: Showing NP-Card for (2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0300197)

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Record Information

Version

2.0

Created at

2022-09-10 12:27:46 UTC

Updated at

2022-09-10 12:27:46 UTC

NP-MRD ID

NP0300197

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(2R,3R,4S,5S,6R)-2-{[(1R,2R)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol 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. (2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Molineria capitulata. Based on a literature review very few articles have been published on (2R,3R,4S,5S,6R)-2-{[(1R,2R)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102214272D          

 38 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102214272D          

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    0.7145   -8.6625    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
   -2.1434   -3.7125    0.0000 C   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
   -2.8579   -2.4750    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  3  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  1  0  0  0
 10 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  2  0  0  0  0
 25 34  1  0  0  0  0
  6 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300197

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)C#CC[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)C1=CC=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O11/c1-33-17-10-8-15(12-20(17)35-3)6-5-7-19(23(29)16-9-11-18(34-2)21(13-16)36-4)37-27-26(32)25(31)24(30)22(14-28)38-27/h8-13,19,22-32H,7,14H2,1-4H3/t19-,22-,23-,24-,25+,26-,27-/m1/s1

> <INCHI_KEY>
IKIFYAWQFDKTCM-OHGANORHSA-N

> <FORMULA>
C27H34O11

> <MOLECULAR_WEIGHT>
534.558

> <EXACT_MASS>
534.210111915

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.6716228927547

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1R,2R)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
0.7207857853333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.015170366084906

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.183252116141764

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835588052473

> <JCHEM_POLAR_SURFACE_AREA>
156.52999999999997

> <JCHEM_REFRACTIVITY>
131.7722

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(1R,2R)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667 -10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334 -16.170   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667 -18.480   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.335 -21.560   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -6.668 -19.250   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.000 -12.320   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335 -16.940   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667 -18.480   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334 -19.250   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -5.335  -6.160   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   12   22                                                  
CONECT   22   21                                                            
CONECT   23   10   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   25                                                       
CONECT   35    6   36                                                       
CONECT   36   35    3   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₁₁

Average Mass

534.5580 Da

Monoisotopic Mass

534.21011 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(1R,2R)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(1R,2R)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)C#CC[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)C1=CC=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C27H34O11/c1-33-17-10-8-15(12-20(17)35-3)6-5-7-19(23(29)16-9-11-18(34-2)21(13-16)36-4)37-27-26(32)25(31)24(30)22(14-28)38-27/h8-13,19,22-32H,7,14H2,1-4H3/t19-,22-,23-,24-,25+,26-,27-/m1/s1

InChI Key

IKIFYAWQFDKTCM-OHGANORHSA-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
Molineria capitulata	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
Hexose monosaccharide
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
O-dimethoxybenzene
Dimethoxybenzene
Fatty alcohol
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Alkyl aryl ether
Monosaccharide
Oxane
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Organic oxygen compound
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Alcohol
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	0.72	ChemAxon
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	156.53 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	131.77 m³·mol⁻¹	ChemAxon
Polarizability	55.67 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

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

163036222

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0300197)

MOL for NP0300197 ((2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0300197 ((2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0300197 ((2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0300197 ((2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0300197 ((2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0300197 ((2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0300197 ((2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0300197 ((2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0300197 ((2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0300197 ((2r,3r,4s,5s,6r)-2-{[(1r,2r)-1,5-bis(3,4-dimethoxyphenyl)-1-hydroxypent-4-yn-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)