NP-MRD: Showing NP-Card for 3,3',4',5,5',8-Hexahydroxyflavone (NP0048740)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 21:01:26 UTC

Updated at

2022-03-17 21:01:26 UTC

NP-MRD ID

NP0048740

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,3',4',5,5',8-Hexahydroxyflavone

Description

3,3',4',5,5',8-Hexahydroxyflavone belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, 3,3',4',5,5',8-hexahydroxyflavone is considered to be a flavonoid lipid molecule. 3,3',4',5,5',8-Hexahydroxyflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3,3',4',5,5',8-Hexahydroxyflavone has been detected, but not quantified in, a few different foods, such as coffee and coffee products, herbs and spices, and pulses. 3,3',4',5,5',8-Hexahydroxyflavone is found in Cassia tora . This could make 3,3',4',5,5',8-hexahydroxyflavone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309442D          

 23 25  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   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
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  5  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
 10  6  2  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14  5  1  0  0  0  0
 14 13  2  0  0  0  0
 15  7  2  0  0  0  0
 15 10  1  0  0  0  0
 16  6  1  0  0  0  0
 17  7  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 20 11  1  0  0  0  0
 21 12  2  0  0  0  0
 22 13  1  0  0  0  0
 23 14  1  0  0  0  0
 23 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048740

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(=CC(O)=C1O)C1=C(O)C(=O)C2=C(O)C=CC(O)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O8/c16-6-1-2-7(17)15-10(6)12(21)13(22)14(23-15)5-3-8(18)11(20)9(19)4-5/h1-4,16-20,22H

> <INCHI_KEY>
JGTKWAPKKUUANC-UHFFFAOYSA-N

> <FORMULA>
C15H10O8

> <MOLECULAR_WEIGHT>
318.2351

> <EXACT_MASS>
318.037567296

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
29.33452151374731

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5,8-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
1.64

> <JCHEM_LOGP>
1.8527341423333332

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.89085285877502

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.8496547903401375

> <JCHEM_PKA_STRONGEST_BASIC>
-4.100160130291372

> <JCHEM_POLAR_SURFACE_AREA>
147.67999999999998

> <JCHEM_REFRACTIVITY>
78.8431

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.34e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,8-trihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   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      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    7                                                       
CONECT    3    5    8                                                       
CONECT    4    5    9                                                       
CONECT    5    3    4   14                                                  
CONECT    6    1   10   16                                                  
CONECT    7    2   15   17                                                  
CONECT    8    3   11   18                                                  
CONECT    9    4   11   19                                                  
CONECT   10    6   12   15                                                  
CONECT   11    8    9   20                                                  
CONECT   12   10   13   21                                                  
CONECT   13   12   14   22                                                  
CONECT   14    5   13   23                                                  
CONECT   15    7   10   23                                                  
CONECT   16    6                                                            
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20   11                                                            
CONECT   21   12                                                            
CONECT   22   13                                                            
CONECT   23   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
3',4',5,5',8-Pentahydroxyflavonol	HMDB
3,5,8,3',4',5'-Hexahydroxyflavone	HMDB
3,5,8-Trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one, 9ci	HMDB

Chemical Formula

C₁₅H₁₀O₈

Average Mass

318.2351 Da

Monoisotopic Mass

318.03757 Da

IUPAC Name

3,5,8-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one

Traditional Name

3,5,8-trihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one

CAS Registry Number

90332-28-8

SMILES

OC1=CC(=CC(O)=C1O)C1=C(O)C(=O)C2=C(O)C=CC(O)=C2O1

InChI Identifier

InChI=1S/C15H10O8/c16-6-1-2-7(17)15-10(6)12(21)13(22)14(23-15)5-3-8(18)11(20)9(19)4-5/h1-4,16-20,22H

InChI Key

JGTKWAPKKUUANC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cassia tora	Plant	KNApSAcK
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavones

Direct Parent

Flavonols

Alternative Parents

Substituents

3-hydroxyflavone
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
8-hydroxyflavonoid
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Benzenetriol
Pyrogallol derivative
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111618 )

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	1.64	ALOGPS
logP	1.85	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.85	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	147.68 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	78.84 m³·mol⁻¹	ChemAxon
Polarizability	29.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037357

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016384

KNApSAcK ID

C00004779

Chemspider ID

24844381

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44258711

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,3',4',5,5',8-Hexahydroxyflavone (NP0048740)

MOL for NP0048740 (3,3',4',5,5',8-Hexahydroxyflavone)

3D MOL for NP0048740 (3,3',4',5,5',8-Hexahydroxyflavone)

3D SDF for NP0048740 (3,3',4',5,5',8-Hexahydroxyflavone)

3D-SDF for NP0048740 (3,3',4',5,5',8-Hexahydroxyflavone)

PDB for NP0048740 (3,3',4',5,5',8-Hexahydroxyflavone)

3D PDB for NP0048740 (3,3',4',5,5',8-Hexahydroxyflavone)

SMILES for NP0048740 (3,3',4',5,5',8-Hexahydroxyflavone)

INCHI for NP0048740 (3,3',4',5,5',8-Hexahydroxyflavone)

Structure for NP0048740 (3,3',4',5,5',8-Hexahydroxyflavone)

3D Structure for NP0048740 (3,3',4',5,5',8-Hexahydroxyflavone)