NP-MRD: Showing NP-Card for Dihydrooroxylin A (NP0137465)

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Record Information

Version

2.0

Created at

2022-05-30 16:53:15 UTC

Updated at

2022-05-30 16:53:15 UTC

NP-MRD ID

NP0137465

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydrooroxylin A

Description

Dihydrooroxylin belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone. Thus, dihydrooroxylin is considered to be a flavonoid lipid molecule. Dihydrooroxylin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Dihydrooroxylin has been detected, but not quantified in, fruits. Dihydrooroxylin A is found in Adenostoma sparsifolium, Beta vulgaris, Nothofagus pumilio, Oroxylum indicum, Peperomia serpens, Pisonia aculeata, Scutellaria baicalensis and Scutellaria lateriflora. Dihydrooroxylin A was first documented in 1998 (PMID: 9621415). This could make dihydrooroxylin a potential biomarker for the consumption of these foods (PMID: 19555121) (PMID: 15279992) (PMID: 9667023).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    4.7271    0.8026    1.6109 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3825    0.1761    0.3988 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1253   -0.2912    0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7384   -1.5636    0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6340   -2.4364    1.0193 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4736   -1.9873    0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5691   -1.1403   -0.5621 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9762    0.1390   -0.8499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2303    0.5870   -0.5400 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6563    1.8676   -0.8244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0039    0.9991   -1.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0586    2.2223   -1.4076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1030    0.3606   -2.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000   -0.7740   -1.5031 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6003   -0.2580   -0.4354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0023    1.0294   -0.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8593    1.4227    0.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2891    0.4505    1.6273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8925   -0.8687    1.4926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0554   -1.2269    0.4723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7002   -1.5801   -0.8831 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8170    1.0575    2.1908 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2639    1.7518    1.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4383    0.1919    2.2120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4097   -3.3774    1.2595 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1607   -2.9944    0.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1229    2.5399   -1.2743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6059   -0.0546   -3.1713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8201    1.1098   -2.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3196   -1.4476   -2.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6630    1.7961   -0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1725    2.4471    0.8644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9581    0.7795    2.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2770   -1.5868    2.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7621   -2.2640    0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  9  2  0
  9 10  1  0
  9  8  1  0
  8  7  2  0
  7 21  1  0
 21 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  7  6  1  0
  6  4  2  0
  4  5  1  0
  4  3  1  0
 11  8  1  0
 20 15  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 10 27  1  0
 14 30  1  6
 13 28  1  0
 13 29  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
  6 26  1  0
  5 25  1  0
M  END

  Mrv0541 05061309422D          

 21 23  0  0  0  0            999 V2000
    3.5724    2.0625    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
   -2.1434   -0.4125    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
   -1.4289    0.0000    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    2.0625    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
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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    1.2375    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    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
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  2  0  0  0  0
 17 10  2  0  0  0  0
 18 11  1  0  0  0  0
 19 15  1  0  0  0  0
 20  1  1  0  0  0  0
 20 16  1  0  0  0  0
 21 12  1  0  0  0  0
 21 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137465

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-6,8,12,18-19H,7H2,1H3

> <INCHI_KEY>
QUAPPCXFYKSDSV-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.332426064960266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-6-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.9810021063333334

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.158229122649372

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.438706483284868

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0040492825048526

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
75.77210000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrooroxylin A

> <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       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -0.770   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      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    9                                                       
CONECT    6    4    9                                                       
CONECT    7   10   12                                                       
CONECT    8   11   13                                                       
CONECT    9    5    6   12                                                  
CONECT   10    7   14   17                                                  
CONECT   11    8   16   18                                                  
CONECT   12    7    9   21                                                  
CONECT   13    8   14   21                                                  
CONECT   14   10   13   15                                                  
CONECT   15   14   16   19                                                  
CONECT   16   11   15   20                                                  
CONECT   17   10                                                            
CONECT   18   11                                                            
CONECT   19   15                                                            
CONECT   20    1   16                                                       
CONECT   21   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
5,7-Dihydroxy-6-methoxyflavanone	ChEBI
Dihydrooroxylin a	HMDB
Dihydrooroxylin	MeSH

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2794 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

5,7-dihydroxy-6-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

dihydrooroxylin A

CAS Registry Number

Not Available

SMILES

COC1=C(O)C2=C(OC(CC2=O)C2=CC=CC=C2)C=C1O

InChI Identifier

InChI=1S/C16H14O5/c1-20-16-11(18)8-13-14(15(16)19)10(17)7-12(21-13)9-5-3-2-4-6-9/h2-6,8,12,18-19H,7H2,1H3

InChI Key

QUAPPCXFYKSDSV-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
Adenostoma sparsifolium	LOTUS Database	35616633
Beta vulgaris	LOTUS Database	35616633
Nothofagus pumilio	LOTUS Database	35616633
Oroxylum indicum	LOTUS Database	35616633
Peperomia serpens	LOTUS Database	35616633
Pisonia aculeata	LOTUS Database	35616633
Scutellaria baicalensis	LOTUS Database	35616633
Scutellaria lateriflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

6-O-methylated flavonoids

Alternative Parents

Substituents

6-methoxyflavonoid-skeleton
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Chromone
Benzopyran
Chromane
1-benzopyran
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monomethoxyflavanone (CHEBI:67376 )
dihydroxyflavanone (CHEBI:67376 )
Flavanones (LMPK12140611 )

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	3.01	ALOGPS
logP	2.98	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.44	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.77 m³·mol⁻¹	ChemAxon
Polarizability	29.33 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

HMDB0037322

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016342

KNApSAcK ID

C00008148

Chemspider ID

4475720

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316733

PDB ID

Not Available

ChEBI ID

67376

Good Scents ID

Not Available

References

General References

Li J, Ding Y, Li XC, Ferreira D, Khan S, Smillie T, Khan IA: Scuteflorins A and B, dihydropyranocoumarins from Scutellaria lateriflora. J Nat Prod. 2009 Jun;72(6):983-7. doi: 10.1021/np900068t. [PubMed:19555121 ]
Thoison O, Sevenet T, Niemeyer HM, Russell GB: Insect antifeedant compounds from Nothofagus dombeyi and N. pumilio. Phytochemistry. 2004 Jul;65(14):2173-6. doi: 10.1016/j.phytochem.2004.04.002. [PubMed:15279992 ]
Li C, Homma M, Ohkura N, Oka K: Stereochemistry and putative origins of flavanones found in post-administration urine of the traditional Chinese remedies shosaiko-to and daisaiko-to. Chem Pharm Bull (Tokyo). 1998 May;46(5):807-11. doi: 10.1248/cpb.46.807. [PubMed:9621415 ]
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Showing NP-Card for Dihydrooroxylin A (NP0137465)

MOL for NP0137465 (Dihydrooroxylin A)

3D MOL for NP0137465 (Dihydrooroxylin A)

3D SDF for NP0137465 (Dihydrooroxylin A)

3D-SDF for NP0137465 (Dihydrooroxylin A)

PDB for NP0137465 (Dihydrooroxylin A)

3D PDB for NP0137465 (Dihydrooroxylin A)

SMILES for NP0137465 (Dihydrooroxylin A)

INCHI for NP0137465 (Dihydrooroxylin A)

Structure for NP0137465 (Dihydrooroxylin A)

3D Structure for NP0137465 (Dihydrooroxylin A)