NP-MRD: Showing NP-Card for 4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate (NP0291456)

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Record Information

Version

1.0

Created at

2022-09-09 22:33:39 UTC

Updated at

2022-09-09 22:33:39 UTC

NP-MRD ID

NP0291456

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate

Description

4,5-Dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxo-4H-chromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as glycosyldiacylglycerols. These are diacylglycerols that carry a saccharide moiety linked to the glycerol. 4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate is found in Aloe perfoliata. 4,5-Dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxo-4H-chromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241509532D          

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M  END

     RDKit          3D

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  Mrv1533004241509532D          

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  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 29 27  1  4  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
 15 38  2  0  0  0  0
  9 38  1  0  0  0  0
 38 39  1  0  0  0  0
  5 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291456

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)CC1=CC(=O)C2=C(C)C=C(O)C(C3OC(CO)C(O)C(O)C3OC(=O)C=CC3=CC=C(O)C=C3)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C28H30O11/c1-13-9-18(32)23(26-22(13)19(33)11-17(37-26)10-14(2)30)27-28(25(36)24(35)20(12-29)38-27)39-21(34)8-5-15-3-6-16(31)7-4-15/h3-9,11,14,20,24-25,27-32,35-36H,10,12H2,1-2H3

> <INCHI_KEY>
WDKRSVFLKZPETK-UHFFFAOYSA-N

> <FORMULA>
C28H30O11

> <MOLECULAR_WEIGHT>
542.537

> <EXACT_MASS>
542.178811786

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
54.113192463179274

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxo-4H-chromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
1.4840386253333333

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.398656084566406

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.199698545686922

> <JCHEM_PKA_STRONGEST_BASIC>
-2.569310884977793

> <JCHEM_POLAR_SURFACE_AREA>
183.20999999999998

> <JCHEM_REFRACTIVITY>
139.6241

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.667  -3.080   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   39                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   38                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   38                                                  
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   31                                                       
CONECT   38   15    9   39                                                  
CONECT   39   38    5                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
4,5-Dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxo-4H-chromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₈H₃₀O₁₁

Average Mass

542.5370 Da

Monoisotopic Mass

542.17881 Da

IUPAC Name

4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxo-4H-chromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(O)CC1=CC(=O)C2=C(C)C=C(O)C(C3OC(CO)C(O)C(O)C3OC(=O)C=CC3=CC=C(O)C=C3)=C2O1

InChI Identifier

InChI=1S/C28H30O11/c1-13-9-18(32)23(26-22(13)19(33)11-17(37-26)10-14(2)30)27-28(25(36)24(35)20(12-29)38-27)39-21(34)8-5-15-3-6-16(31)7-4-15/h3-9,11,14,20,24-25,27-32,35-36H,10,12H2,1-2H3

InChI Key

WDKRSVFLKZPETK-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
Aloe perfoliata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosyldiacylglycerols. These are diacylglycerols that carry a saccharide moiety linked to the glycerol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Glycosylglycerols

Direct Parent

Glycosyldiacylglycerols

Alternative Parents

Substituents

Glycosyldiacylglycerol
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Octadecanoid
Disaccharide
Glycosyl compound
O-glycosyl compound
Fatty acid ester
Fatty acyl
Oxane
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Acetal
Primary alcohol
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
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	1.71	ALOGPS
logP	1.48	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	6.2	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	139.62 m³·mol⁻¹	ChemAxon
Polarizability	54.11 Å³	ChemAxon
Number of Rings	4	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate (NP0291456)

MOL for NP0291456 (4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate)

3D MOL for NP0291456 (4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate)

3D SDF for NP0291456 (4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate)

3D-SDF for NP0291456 (4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate)

PDB for NP0291456 (4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate)

3D PDB for NP0291456 (4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate)

SMILES for NP0291456 (4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate)

INCHI for NP0291456 (4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate)

Structure for NP0291456 (4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate)

3D Structure for NP0291456 (4,5-dihydroxy-2-[7-hydroxy-2-(2-hydroxypropyl)-5-methyl-4-oxochromen-8-yl]-6-(hydroxymethyl)oxan-3-yl 3-(4-hydroxyphenyl)prop-2-enoate)