NP-MRD: Showing NP-Card for 2',3,5,6',7-Pentahydroxyflavanone (NP0140242)

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Record Information

Version

2.0

Created at

2022-06-29 21:15:57 UTC

Updated at

2022-06-29 21:15:57 UTC

NP-MRD ID

NP0140242

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2',3,5,6',7-Pentahydroxyflavanone

Description

80366-15-0 Belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively. 2',3,5,6',7-Pentahydroxyflavanone is found in Scutellaria baicalensis and Scutellaria rehderiana. 80366-15-0 Is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -1.6277   -2.4447    2.0180 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1725   -1.5116    1.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0386   -0.6086    0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3496   -0.5230    0.9324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8414   -1.2629    1.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820    0.3244    0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6550    1.0607   -0.7951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5246    1.9171   -1.4565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    0.9499   -1.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4551    0.0878   -0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1485   -0.0498   -0.8256 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7704   -0.9573   -0.2379 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0547   -0.2480    0.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2202   -0.9696   -0.0109 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -2.3380   -0.2280 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4287   -0.2972    0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4664    1.0693    0.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2867    1.8054    0.4387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0877    1.1381    0.2758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8775    1.8290    0.3296 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2718   -1.3748    1.1478 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8120   -0.6037    2.1601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8236   -1.2293    2.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2035    0.3991    0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6994    2.8772   -1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9253    1.5500   -1.9881 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9609   -1.7832   -0.9169 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4455   -2.9218   -0.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3473   -0.9147    0.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4392    1.5620    0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3402    2.8935    0.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9299    2.8446    0.4557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6988   -2.4300    1.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2896    0.1602    2.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  6  4  1  0
  4  5  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
  2 21  1  0
 19 13  1  0
  3 10  1  0
 22 34  1  0
 21 33  1  1
 12 27  1  6
  9 26  1  0
  8 25  1  0
  6 24  1  0
  5 23  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
 18 31  1  0
 20 32  1  0
M  END


  Mrv1533004171500582D          

 22 24  0  0  0  0            999 V2000
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
   -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 O   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
   -0.7145    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
    0.7145    1.2375    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
  3  4  1  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  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140242

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=C(O)C=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O7/c16-6-4-9(19)12-10(5-6)22-15(14(21)13(12)20)11-7(17)2-1-3-8(11)18/h1-5,14-19,21H

> <INCHI_KEY>
NBQYBZYBTNQEQG-UHFFFAOYSA-N

> <FORMULA>
C15H12O7

> <MOLECULAR_WEIGHT>
304.254

> <EXACT_MASS>
304.058302726

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.56084301503684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2,6-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
1.8163842679999997

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.732187921783881

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.719555713787564

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0790680964589585

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
74.6089

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2,6-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   1.540   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  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    5   13                                                  
CONECT   13   12    2   14                                                  
CONECT   14   13                                                            
CONECT   15    3   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   15   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
Ganhuangemin	MeSH

Chemical Formula

C₁₅H₁₂O₇

Average Mass

304.2540 Da

Monoisotopic Mass

304.05830 Da

IUPAC Name

2-(2,6-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

2-(2,6-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

OC1C(OC2=CC(O)=CC(O)=C2C1=O)C1=C(O)C=CC=C1O

InChI Identifier

InChI=1S/C15H12O7/c16-6-4-9(19)12-10(5-6)22-15(14(21)13(12)20)11-7(17)2-1-3-8(11)18/h1-5,14-19,21H

InChI Key

NBQYBZYBTNQEQG-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
Scutellaria baicalensis	LOTUS Database	35616633
Scutellaria rehderiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanonols

Alternative Parents

Substituents

3-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanonol
Hydroxyflavonoid
Chromone
Chromane
Benzopyran
1-benzopyran
Resorcinol
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Oxacycle
Polyol
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
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	1.01	ALOGPS
logP	1.82	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	7.72	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.61 m³·mol⁻¹	ChemAxon
Polarizability	28.56 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

71307292

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2',3,5,6',7-Pentahydroxyflavanone (NP0140242)

MOL for NP0140242 (2',3,5,6',7-Pentahydroxyflavanone)

3D MOL for NP0140242 (2',3,5,6',7-Pentahydroxyflavanone)

3D SDF for NP0140242 (2',3,5,6',7-Pentahydroxyflavanone)

3D-SDF for NP0140242 (2',3,5,6',7-Pentahydroxyflavanone)

PDB for NP0140242 (2',3,5,6',7-Pentahydroxyflavanone)

3D PDB for NP0140242 (2',3,5,6',7-Pentahydroxyflavanone)

SMILES for NP0140242 (2',3,5,6',7-Pentahydroxyflavanone)

INCHI for NP0140242 (2',3,5,6',7-Pentahydroxyflavanone)

Structure for NP0140242 (2',3,5,6',7-Pentahydroxyflavanone)

3D Structure for NP0140242 (2',3,5,6',7-Pentahydroxyflavanone)