NP-MRD: Showing NP-Card for 3'-O-Methylorobol (NP0138266)

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Record Information

Version

2.0

Created at

2022-05-31 17:17:46 UTC

Updated at

2022-05-31 17:17:46 UTC

NP-MRD ID

NP0138266

Secondary Accession Numbers

NP0056551

Natural Product Identification

Common Name

3'-O-Methylorobol

Description

5,7-Dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one, also known as 5,7,4'-trihydroxy-3'-methoxyisoflavone, belongs to the class of organic compounds known as 3'-o-methylisoflavones. These are flavones with methoxy groups attached to the C2' atom of the isoflavone backbone. Thus, 5,7-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one is considered to be a flavonoid lipid molecule. A hydroxyisoflavone that is orobol in which the hydroxy group at position 3' has been replaced by a methoxy group. 5,7-Dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
    4.3419    1.2300    0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2801    1.2824   -0.8779 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1080    0.8700   -1.4951 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0197    0.4172   -0.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8444    0.0021   -1.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3037   -0.4760   -0.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0016   -1.6174   -0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0350   -2.0496   -0.2948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4925   -1.4515    0.7833 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5842   -1.9573    1.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0648   -1.3303    2.5889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1550   -1.8680    3.2299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4232   -0.1885    3.0224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3291    0.3404    2.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6660    1.4692    2.7663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8638   -0.3086    1.2319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7591    0.1753    0.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840    1.2154    0.9274 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8036    0.0618   -2.7566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8498    0.5003   -3.5046 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0124    0.9089   -2.8843 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0926    1.3601   -3.6275 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7739    2.0467    0.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0332    0.2160    0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4056    1.3704    0.8484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0855    0.3838    0.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298   -2.1220   -1.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0776   -2.8676    1.0927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1170   -1.6435    3.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7672    0.3331    3.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8714    2.0446    3.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1186   -0.2638   -3.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7732    0.5295   -4.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197    1.3871   -4.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 21  2  0
 21 22  1  0
 21 20  1  0
 20 19  2  0
 19  5  1  0
  5  4  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
  4  3  1  0
 17  6  1  0
 16  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 22 34  1  0
 20 33  1  0
 19 32  1  0
  4 26  1  0
  7 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
M  END

  Mrv1652308231920202D          

 22 24  0  0  0  0            999 V2000
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    5.0013    3.7125    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
    2.1434    2.0625    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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    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    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    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
  3  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 12  5  1  0  0  0  0
 13  4  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  2  0  0  0  0
 15 12  2  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21 13  1  0  0  0  0
 22  7  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138266

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C1=COC2=CC(O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-13-4-8(2-3-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-7,17-19H,1H3

> <INCHI_KEY>
ZMFBGWWGXBNJAC-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.266

> <EXACT_MASS>
300.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.446375640957818

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.9192011239999993

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.127762497339484

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.54699731975155

> <JCHEM_PKA_STRONGEST_BASIC>
-4.763855676792214

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
78.1461

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3'-O-methylorobol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.003   6.930   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   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    8                                                       
CONECT    3    2   11                                                       
CONECT    4    8   13                                                       
CONECT    5    9   12                                                       
CONECT    6    9   14                                                       
CONECT    7   10   22                                                       
CONECT    8    2    4   10                                                  
CONECT    9    5    6   17                                                  
CONECT   10    7    8   16                                                  
CONECT   11    3   13   18                                                  
CONECT   12    5   15   19                                                  
CONECT   13    4   11   21                                                  
CONECT   14    6   15   22                                                  
CONECT   15   12   14   16                                                  
CONECT   16   10   15   20                                                  
CONECT   17    9                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   16                                                            
CONECT   21    1   13                                                       
CONECT   22    7   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
5,7,4'-Trihydroxy-3'-methoxyisoflavone	ChEBI

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2660 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

5,7-dihydroxy-3-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one

Traditional Name

3'-O-methylorobol

CAS Registry Number

36190-95-1

SMILES

COC1=C(O)C=CC(=C1)C1=COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C16H12O6/c1-21-13-4-8(2-3-11(13)18)10-7-22-14-6-9(17)5-12(19)15(14)16(10)20/h2-7,17-19H,1H3

InChI Key

ZMFBGWWGXBNJAC-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-o-methylisoflavones. These are flavones with methoxy groups attached to the C2' atom of the isoflavone backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-O-methylisoflavones

Alternative Parents

Substituents

3p-methoxyisoflavone
Isoflavone
Hydroxyisoflavonoid
Chromone
Methoxyphenol
1-benzopyran
Benzopyran
Phenoxy compound
Phenol ether
Methoxybenzene
Anisole
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Ether
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavone (CHEBI:70032 )
methoxyisoflavone (CHEBI:70032 )
Isoflavonoids (LMPK12050258 )

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	3.05	ALOGPS
logP	2.92	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.55	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.15 m³·mol⁻¹	ChemAxon
Polarizability	29.45 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

HMDB0140564

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093154

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

5319744

PDB ID

Not Available

ChEBI ID

70032

Good Scents ID

Not Available

References

General References

Showing NP-Card for 3'-O-Methylorobol (NP0138266)

MOL for NP0138266 (3'-O-Methylorobol)

3D MOL for NP0138266 (3'-O-Methylorobol)

3D SDF for NP0138266 (3'-O-Methylorobol)

3D-SDF for NP0138266 (3'-O-Methylorobol)

PDB for NP0138266 (3'-O-Methylorobol)

3D PDB for NP0138266 (3'-O-Methylorobol)

SMILES for NP0138266 (3'-O-Methylorobol)

INCHI for NP0138266 (3'-O-Methylorobol)

Structure for NP0138266 (3'-O-Methylorobol)

3D Structure for NP0138266 (3'-O-Methylorobol)