NP-MRD: Showing NP-Card for 2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one (NP0049810)

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Record Information

Version

2.0

Created at

2022-03-17 21:18:29 UTC

Updated at

2022-03-17 21:18:30 UTC

NP-MRD ID

NP0049810

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one

Description

2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-B']dipyran-4-one, also known as 4'-hydroxy-3,6-dimethoxy-6'',6''-dimethylpyrano[2,3:7,8]Flavone, belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton. 2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-B']dipyran-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-B']dipyran-4-one has been detected, but not quantified in, citrus and mandarin orange (clementine, tangerine). This could make 2-(4-hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-B']dipyran-4-one a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061312292D          

 28 31  0  0  0  0            999 V2000
    4.6465   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 10  9  2  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 12  1  0  0  0  0
 20 14  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 21 19  2  0  0  0  0
 22  1  1  0  0  0  0
 22  2  1  0  0  0  0
 22 10  1  0  0  0  0
 23 13  1  0  0  0  0
 24 18  2  0  0  0  0
 25  3  1  0  0  0  0
 25 16  1  0  0  0  0
 26  4  1  0  0  0  0
 26 21  1  0  0  0  0
 27 19  1  0  0  0  0
 27 20  1  0  0  0  0
 28 15  1  0  0  0  0
 28 22  1  0  0  0  0
M  END


  Mrv0541 05061312292D          

 28 31  0  0  0  0            999 V2000
    4.6465   -0.1178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6465    0.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 10  9  2  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 11  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 16  2  0  0  0  0
 18 17  1  0  0  0  0
 19 12  1  0  0  0  0
 20 14  2  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 21 19  2  0  0  0  0
 22  1  1  0  0  0  0
 22  2  1  0  0  0  0
 22 10  1  0  0  0  0
 23 13  1  0  0  0  0
 24 18  2  0  0  0  0
 25  3  1  0  0  0  0
 25 16  1  0  0  0  0
 26  4  1  0  0  0  0
 26 21  1  0  0  0  0
 27 19  1  0  0  0  0
 27 20  1  0  0  0  0
 28 15  1  0  0  0  0
 28 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049810

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(=O)C(OC)=C(OC2=C2C=CC(C)(C)OC2=C1)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H20O6/c1-22(2)10-9-14-15(28-22)11-16(25-3)17-18(24)21(26-4)19(27-20(14)17)12-5-7-13(23)8-6-12/h5-11,23H,1-4H3

> <INCHI_KEY>
VNNMTQJSNKAONW-UHFFFAOYSA-N

> <FORMULA>
C22H20O6

> <MOLECULAR_WEIGHT>
380.3906

> <EXACT_MASS>
380.125988372

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
40.28328353777982

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxyphenyl)-3,5-dimethoxy-8,8-dimethyl-4H,8H-pyrano[2,3-h]chromen-4-one

> <ALOGPS_LOGP>
4.36

> <JCHEM_LOGP>
3.2727749546666662

> <ALOGPS_LOGS>
-4.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.545202268183248

> <JCHEM_PKA_STRONGEST_BASIC>
-4.426866866450909

> <JCHEM_POLAR_SURFACE_AREA>
74.22000000000001

> <JCHEM_REFRACTIVITY>
106.52729999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.27e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-hydroxyphenyl)-3,5-dimethoxy-8,8-dimethylpyrano[2,3-h]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       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.673   1.760   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.564   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.746  -1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564  -3.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.516  -3.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.206  -4.565   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.206  -1.897   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.746  -4.565   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.516  -5.898   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.104   4.771   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.746   0.770   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.104  -0.564   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.724   2.104   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2   22                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5    7   12                                                       
CONECT    6    8   12                                                       
CONECT    7    5   13                                                       
CONECT    8    6   13                                                       
CONECT    9   10   14                                                       
CONECT   10    9   22                                                       
CONECT   11   15   16                                                       
CONECT   12    5    6   19                                                  
CONECT   13    7    8   23                                                  
CONECT   14    9   15   20                                                  
CONECT   15   11   14   28                                                  
CONECT   16   11   17   25                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   21   24                                                  
CONECT   19   12   21   27                                                  
CONECT   20   14   17   27                                                  
CONECT   21   18   19   26                                                  
CONECT   22    1    2   10   28                                             
CONECT   23   13                                                            
CONECT   24   18                                                            
CONECT   25    3   16                                                       
CONECT   26    4   21                                                       
CONECT   27   19   20                                                       
CONECT   28   15   22                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
4'-Hydroxy-3,6-dimethoxy-6'',6''-dimethylpyrano[2,3:7,8]flavone	HMDB

Chemical Formula

C₂₂H₂₀O₆

Average Mass

380.3906 Da

Monoisotopic Mass

380.12599 Da

IUPAC Name

2-(4-hydroxyphenyl)-3,5-dimethoxy-8,8-dimethyl-4H,8H-pyrano[2,3-h]chromen-4-one

Traditional Name

2-(4-hydroxyphenyl)-3,5-dimethoxy-8,8-dimethylpyrano[2,3-h]chromen-4-one

CAS Registry Number

157072-30-5

SMILES

COC1=C2C(=O)C(OC)=C(OC2=C2C=CC(C)(C)OC2=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C22H20O6/c1-22(2)10-9-14-15(28-22)11-16(25-3)17-18(24)21(26-4)19(27-20(14)17)12-5-7-13(23)8-6-12/h5-11,23H,1-4H3

InChI Key

VNNMTQJSNKAONW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus reticulata	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoflavonoids. Pyranoflavonoids are compounds containing a pyran ring fused to a 2-phenyl-1,4-benzopyran skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Pyranoflavonoids

Direct Parent

Pyranoflavonoids

Alternative Parents

Substituents

Pyranoflavonoid
3-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Monohydroxyflavonoid
Pyranochromene
3-methoxychromone
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
1-benzopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous ester
Heteroaromatic compound
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
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	4.36	ALOGPS
logP	3.27	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	8.55	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.53 m³·mol⁻¹	ChemAxon
Polarizability	40.28 Å³	ChemAxon
Number of Rings	4	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

HMDB0041236

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021139

KNApSAcK ID

C00005079

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

131753080

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one (NP0049810)

MOL for NP0049810 (2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one)

3D MOL for NP0049810 (2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one)

3D SDF for NP0049810 (2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one)

3D-SDF for NP0049810 (2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one)

PDB for NP0049810 (2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one)

3D PDB for NP0049810 (2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one)

SMILES for NP0049810 (2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one)

INCHI for NP0049810 (2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one)

Structure for NP0049810 (2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one)

3D Structure for NP0049810 (2-(4-Hydroxyphenyl)-3,6-dimethoxy-8,8-dimethyl-4H,8H-benzo[1,2-b:3,4-b']dipyran-4-one)