NP-MRD: Showing NP-Card for 3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one (NP0208250)

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Record Information

Version

2.0

Created at

2022-09-05 05:10:35 UTC

Updated at

2022-09-05 05:10:35 UTC

NP-MRD ID

NP0208250

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one

Description

3,7-Bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. 3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one is found in Aconitum orientale and Macroptilium atropurpureum. 3,7-Bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121514252D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 04121514252D          

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   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6674   -2.9599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4521   -2.7050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -3.7445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974   -4.4120    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 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
 18 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 13 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 11 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  2  0  0  0  0
  9 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
  6 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
  4 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0208250

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C1OC(OC2=CC(O)=C3C(OC(C4=CC=C(O)C=C4)=C(OC4OC(C(C)O)C(O)C4O)C3=O)=C2)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O14/c1-9(28)22-18(33)20(35)26(39-22)37-13-7-14(31)16-15(8-13)38-24(11-3-5-12(30)6-4-11)25(17(16)32)41-27-21(36)19(34)23(40-27)10(2)29/h3-10,18-23,26-31,33-36H,1-2H3

> <INCHI_KEY>
UREPCGRALLQPJF-UHFFFAOYSA-N

> <FORMULA>
C27H30O14

> <MOLECULAR_WEIGHT>
578.523

> <EXACT_MASS>
578.163555646

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
55.83502264761286

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
0.59

> <JCHEM_LOGP>
-0.015518134333332045

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.556797975021656

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.083347287331231

> <JCHEM_PKA_STRONGEST_BASIC>
-3.05570121226946

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999997

> <JCHEM_REFRACTIVITY>
136.35160000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       1.049  -9.643   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.675  -8.236   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.207  -8.075   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.770  -6.990   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.246  -5.525   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.743  -0.144   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      11.773  -1.288   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.305  -1.127   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.931   0.280   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.210  -2.373   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      11.003  -2.622   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      11.629  -4.029   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.497  -2.302   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.352  -3.332   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.246  -5.525   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -2.711  -5.049   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -0.770  -6.990   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.675  -8.236   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   40                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   38                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10   31                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   28                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   17   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   15   24                                                  
CONECT   24   23                                                            
CONECT   25   13   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   11   29                                                  
CONECT   29   28    8   30                                                  
CONECT   30   29                                                            
CONECT   31    9   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    6   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38    4   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₁₄

Average Mass

578.5230 Da

Monoisotopic Mass

578.16356 Da

IUPAC Name

3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

CC(O)C1OC(OC2=CC(O)=C3C(OC(C4=CC=C(O)C=C4)=C(OC4OC(C(C)O)C(O)C4O)C3=O)=C2)C(O)C1O

InChI Identifier

InChI=1S/C27H30O14/c1-9(28)22-18(33)20(35)26(39-22)37-13-7-14(31)16-15(8-13)38-24(11-3-5-12(30)6-4-11)25(17(16)32)41-27-21(36)19(34)23(40-27)10(2)29/h3-10,18-23,26-31,33-36H,1-2H3

InChI Key

UREPCGRALLQPJF-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
Aconitum orientale	LOTUS Database	35616633
Macroptilium atropurpureum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
Flavonoid-3-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
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	0.59	ALOGPS
logP	-0.016	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.08	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	136.35 m³·mol⁻¹	ChemAxon
Polarizability	55.84 Å³	ChemAxon
Number of Rings	5	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 3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one (NP0208250)

MOL for NP0208250 (3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D MOL for NP0208250 (3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D SDF for NP0208250 (3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D-SDF for NP0208250 (3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one)

PDB for NP0208250 (3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D PDB for NP0208250 (3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one)

SMILES for NP0208250 (3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one)

INCHI for NP0208250 (3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one)

Structure for NP0208250 (3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one)

3D Structure for NP0208250 (3,7-bis({[3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]oxy})-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one)