NP-MRD: Showing NP-Card for 4,5-dihydroxy-2-({7'-hydroxy-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate (NP0143555)

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Record Information

Version

2.0

Created at

2022-09-01 22:21:04 UTC

Updated at

2022-09-01 22:21:04 UTC

NP-MRD ID

NP0143555

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5-dihydroxy-2-({7'-hydroxy-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate

Description

4,5-Dihydroxy-2-({7'-hydroxy-2H,2'H-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. 4,5-dihydroxy-2-({7'-hydroxy-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate is found in Daphne feddei. 4,5-Dihydroxy-2-({7'-hydroxy-2H,2'H-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251502392D          

 38 42  0  0  0  0            999 V2000
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004251502392D          

 38 42  0  0  0  0            999 V2000
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 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0143555

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C(O)C(O)C(CO)OC1OC1=CC=C2C=CC(=O)OC2=C1C1=C(O)C=CC2=C1OC(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C26H22O12/c1-11(28)34-25-22(33)21(32)16(10-27)36-26(25)35-15-7-3-13-5-9-18(31)38-24(13)20(15)19-14(29)6-2-12-4-8-17(30)37-23(12)19/h2-9,16,21-22,25-27,29,32-33H,10H2,1H3

> <INCHI_KEY>
KNWQEJAJYAGDAO-UHFFFAOYSA-N

> <FORMULA>
C26H22O12

> <MOLECULAR_WEIGHT>
526.45

> <EXACT_MASS>
526.111126148

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
49.76929473602036

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5-dihydroxy-2-{[8-(7-hydroxy-2-oxo-2H-chromen-8-yl)-2-oxo-2H-chromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl acetate

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
0.8066254503333322

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.695233772643274

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.303308766041485

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092992077375

> <JCHEM_POLAR_SURFACE_AREA>
178.27999999999997

> <JCHEM_REFRACTIVITY>
127.43310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-dihydroxy-2-{[8-(7-hydroxy-2-oxochromen-8-yl)-2-oxochromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.002  -9.240   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   37                                                  
CONECT    6    5    7   31                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11   18                                                  
CONECT   18   17    8   19                                                  
CONECT   19   18   20   30                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   19   24                                                  
CONECT   31    6   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    5   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
4,5-Dihydroxy-2-({7'-hydroxy-2H,2'H-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetic acid	Generator

Chemical Formula

C₂₆H₂₂O₁₂

Average Mass

526.4500 Da

Monoisotopic Mass

526.11113 Da

IUPAC Name

4,5-dihydroxy-2-{[8-(7-hydroxy-2-oxo-2H-chromen-8-yl)-2-oxo-2H-chromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl acetate

Traditional Name

4,5-dihydroxy-2-{[8-(7-hydroxy-2-oxochromen-8-yl)-2-oxochromen-7-yl]oxy}-6-(hydroxymethyl)oxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C(O)C(O)C(CO)OC1OC1=CC=C2C=CC(=O)OC2=C1C1=C(O)C=CC2=C1OC(=O)C=C2

InChI Identifier

InChI=1S/C26H22O12/c1-11(28)34-25-22(33)21(32)16(10-27)36-26(25)35-15-7-3-13-5-9-18(31)38-24(13)20(15)19-14(29)6-2-12-4-8-17(30)37-23(12)19/h2-9,16,21-22,25-27,29,32-33H,10H2,1H3

InChI Key

KNWQEJAJYAGDAO-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
Daphne feddei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Coumarin glycosides

Direct Parent

Coumarin glycosides

Alternative Parents

Substituents

Coumarin-7-o-glycoside
Coumarin o-glycoside
Phenolic glycoside
7-hydroxycoumarin
Hexose monosaccharide
Hydroxycoumarin
Glycosyl compound
O-glycosyl compound
1-benzopyran
Benzopyran
Pyranone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Lactone
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Organooxygen compound
Hydrocarbon derivative
Primary alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
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
logP	1.69	ALOGPS
logP	0.81	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	178.28 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.43 m³·mol⁻¹	ChemAxon
Polarizability	49.77 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

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-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate (NP0143555)

MOL for NP0143555 (4,5-dihydroxy-2-({7'-hydroxy-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate)

3D MOL for NP0143555 (4,5-dihydroxy-2-({7'-hydroxy-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate)

3D SDF for NP0143555 (4,5-dihydroxy-2-({7'-hydroxy-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate)

3D-SDF for NP0143555 (4,5-dihydroxy-2-({7'-hydroxy-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate)

PDB for NP0143555 (4,5-dihydroxy-2-({7'-hydroxy-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate)

3D PDB for NP0143555 (4,5-dihydroxy-2-({7'-hydroxy-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate)

SMILES for NP0143555 (4,5-dihydroxy-2-({7'-hydroxy-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate)

INCHI for NP0143555 (4,5-dihydroxy-2-({7'-hydroxy-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate)

Structure for NP0143555 (4,5-dihydroxy-2-({7'-hydroxy-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate)

3D Structure for NP0143555 (4,5-dihydroxy-2-({7'-hydroxy-[8,8'-bichromene]-2,2'-diyl}oxy)-6-(hydroxymethyl)oxan-3-yl acetate)