NP-MRD: Showing NP-Card for 8-demethylduartin (NP0209139)

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Record Information

Version

2.0

Created at

2022-09-05 06:25:57 UTC

Updated at

2022-09-05 06:25:57 UTC

NP-MRD ID

NP0209139

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-demethylduartin

Description

3-(3-Hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7,8-diol belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. Thus, 3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7,8-diol is considered to be a flavonoid lipid molecule. 8-demethylduartin is found in Dalbergia parviflora. 3-(3-Hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7,8-diol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
    5.1944   -0.9186   -2.2720 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8302   -0.2317   -1.1228 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5559   -0.3495   -0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5855   -1.1372   -1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3438   -1.2038   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0454   -0.4956    0.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3053   -0.5704    1.2061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9533   -1.8415    0.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640   -1.6129   -0.5283 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6722   -0.6409   -0.4929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071    0.4726    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3969    1.4433    0.3039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5784    1.2875   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8620    0.1742   -1.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0567    0.0111   -1.8133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8784   -0.7931   -1.1772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0588   -1.9569   -1.9147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1309    0.6338    0.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0309    0.2778    1.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7880    1.0044    2.2773 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3567    2.3401    2.1670 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3010    0.3833    0.5712 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2641    1.1856    1.1555 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2937   -1.1483   -2.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0348   -0.2437   -3.1653 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6936   -1.8723   -2.4556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7504   -1.7092   -2.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5834   -1.8309   -1.0241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2159   -0.7281    2.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2365   -2.6751    0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6646   -2.2254    1.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874    2.3244    0.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3288    2.0841   -0.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7387    0.7612   -1.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3901   -2.6879   -1.9876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2782    1.2118    1.9190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5150    1.3101    0.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2433    2.6859    1.1198 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    2.5511    2.7810 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1463    3.0422    2.5858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0182    1.6885    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 22  2  0
 22 23  1  0
 22 19  1  0
 19 20  1  0
 20 21  1  0
 19  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 18  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
  4  3  1  0
 18  7  1  0
 16 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 23 41  1  0
 21 38  1  0
 21 39  1  0
 21 40  1  0
  5 28  1  0
  4 27  1  0
  7 29  1  1
  8 30  1  0
  8 31  1  0
 18 36  1  0
 18 37  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 17 35  1  0
M  END


  Mrv1652308221902212D          

 23 25  0  0  0  0            999 V2000
    6.4302    2.0625    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    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
    5.7158    0.0000    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   -1.2375    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
    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 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
    5.7158    0.8250    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
    5.0013    1.2375    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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  9  3  1  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 11 10  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 14 12  2  0  0  0  0
 15 13  2  0  0  0  0
 16  9  2  0  0  0  0
 16 14  1  0  0  0  0
 17 11  2  0  0  0  0
 17 15  1  0  0  0  0
 18 12  1  0  0  0  0
 19 14  1  0  0  0  0
 20 15  1  0  0  0  0
 21  1  1  0  0  0  0
 21 13  1  0  0  0  0
 22  2  1  0  0  0  0
 22 17  1  0  0  0  0
 23  8  1  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0209139

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C(OC)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O6/c1-21-13-6-4-11(17(22-2)15(13)20)10-7-9-3-5-12(18)14(19)16(9)23-8-10/h3-6,10,18-20H,7-8H2,1-2H3

> <INCHI_KEY>
FKSLFBLGVHYQCL-UHFFFAOYSA-N

> <FORMULA>
C17H18O6

> <MOLECULAR_WEIGHT>
318.325

> <EXACT_MASS>
318.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.940188135481755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7,8-diol

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
2.572770024333333

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.951884916333574

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.25696767645752

> <JCHEM_PKA_STRONGEST_BASIC>
-4.431014433760632

> <JCHEM_POLAR_SURFACE_AREA>
88.38000000000001

> <JCHEM_REFRACTIVITY>
83.8675

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-demethylduartin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   0.000   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      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    5    9                                                       
CONECT    4    6   11                                                       
CONECT    5    3   12                                                       
CONECT    6    4   13                                                       
CONECT    7    9   10                                                       
CONECT    8   10   23                                                       
CONECT    9    3    7   16                                                  
CONECT   10    7    8   11                                                  
CONECT   11    4   10   17                                                  
CONECT   12    5   14   18                                                  
CONECT   13    6   15   21                                                  
CONECT   14   12   16   19                                                  
CONECT   15   13   17   20                                                  
CONECT   16    9   14   23                                                  
CONECT   17   11   15   22                                                  
CONECT   18   12                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21    1   13                                                       
CONECT   22    2   17                                                       
CONECT   23    8   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
(3S)-8-Demethylduartin	ChEMBL, HMDB

Chemical Formula

C₁₇H₁₈O₆

Average Mass

318.3250 Da

Monoisotopic Mass

318.11034 Da

IUPAC Name

3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7,8-diol

Traditional Name

8-demethylduartin

CAS Registry Number

Not Available

SMILES

COC1=C(O)C(OC)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2O

InChI Identifier

InChI=1S/C17H18O6/c1-21-13-6-4-11(17(22-2)15(13)20)10-7-9-3-5-12(18)14(19)16(9)23-8-10/h3-6,10,18-20H,7-8H2,1-2H3

InChI Key

FKSLFBLGVHYQCL-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
Dalbergia parviflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

3'-hydroxy,4'-methoxyisoflavonoids

Alternative Parents

Substituents

3'-hydroxy,4'-methoxyisoflavonoid
2p-methoxyisoflavonoid-skeleton
Isoflavanol
Hydroxyisoflavonoid
Isoflavan
Benzopyran
M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Chromane
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavans (LMPK12080039 )

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	2.31	ALOGPS
logP	2.57	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.26	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	88.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.87 m³·mol⁻¹	ChemAxon
Polarizability	32.94 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

HMDB0130883

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB089510

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

44257513

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-demethylduartin (NP0209139)

MOL for NP0209139 (8-demethylduartin)

3D MOL for NP0209139 (8-demethylduartin)

3D SDF for NP0209139 (8-demethylduartin)

3D-SDF for NP0209139 (8-demethylduartin)

PDB for NP0209139 (8-demethylduartin)

3D PDB for NP0209139 (8-demethylduartin)

SMILES for NP0209139 (8-demethylduartin)

INCHI for NP0209139 (8-demethylduartin)

Structure for NP0209139 (8-demethylduartin)

3D Structure for NP0209139 (8-demethylduartin)