NP-MRD: Showing NP-Card for (R)-4-Methoxydalbergione (NP0051476)

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Record Information

Version

2.0

Created at

2022-04-27 22:49:41 UTC

Updated at

2022-04-27 22:49:42 UTC

NP-MRD ID

NP0051476

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(R)-4-Methoxydalbergione

Description

(R)-4''-methoxydalbergione belongs to the class of organic compounds known as dalbergiones. These are quinone derivatives containing a dalbergione moiety, which consists of a 1-4 quinone conjugated to a phenyl group at ring carbon 2. Thus, (R)-4''-methoxydalbergione is considered to be a flavonoid (R)-4''-methoxydalbergione is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (R)-4-Methoxydalbergione is found in Dalbergia cochinchinensis, Dalbergia latifolia, Dalbergia nigra, Dalbergia odorifera, Dalbergia parviflora, Dalbergia retusa, Dalbergia spp. and Ranunculus repens. Based on a literature review very few articles have been published on (R)-4''-methoxydalbergione.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -1.5776   -3.3625   -0.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5504   -2.0927   -0.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9697   -1.0061    0.4178 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4097   -0.7173    0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834   -0.8318    0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7622   -0.5466    0.6475 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -0.6949    1.5875 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1427   -0.1057   -0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796    0.1630   -0.9264 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0592    1.2996   -0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1952    0.0147   -1.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7810   -0.2752   -1.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0933   -0.1394   -2.2246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8751    0.1672    0.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5361    1.4352    0.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4674    2.4737    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7646    2.2712    0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1057    0.9978    0.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1817   -0.0266    0.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1695   -3.6701    0.8126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9948   -4.1164   -0.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9536   -1.7779   -1.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9960   -1.4675    1.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0930   -1.1669    1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5342    2.2375   -0.5558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9947    1.1833    0.8293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1309    1.3772   -0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4625    0.3429   -2.5758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5520    1.6513   -0.3044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1749    3.4671   -0.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4671    3.0977    0.4575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1230    0.8399    1.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4800   -1.0218    1.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 12  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  3 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6  8  1  0
 19 14  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
  5 24  1  0
  3 23  1  1
  2 22  1  0
  1 20  1  0
  1 21  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
M  END


  Mrv1652304282200492D          

 19 20  0  0  1  0            999 V2000
    2.1434   -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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
    1.4289   -1.6500    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
    2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  2  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  1 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051476

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=O)C(=CC1=O)[C@H](C=C)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O3/c1-3-12(11-7-5-4-6-8-11)13-9-15(18)16(19-2)10-14(13)17/h3-10,12H,1H2,2H3/t12-/m1/s1

> <INCHI_KEY>
RGSUZUQISVAJJF-GFCCVEGCSA-N

> <FORMULA>
C16H14O3

> <MOLECULAR_WEIGHT>
254.285

> <EXACT_MASS>
254.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.706131005278607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-5-[(1R)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
3.019806421333333

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.940178735594977

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
75.9942

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(R)-4-methoxydalbergione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2    7   18                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    1   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
(R)-4-Methoxydalbergione	ChEBI
2-Methoxy-5-(1-phenylallyl)-4-benzoquinone	ChEBI
2-Methoxy-5-(1-phenylallyl)-p-benzoquinone	ChEBI
4-Methoxydalbergione	MeSH
4-Methoxydalbergione, (R)-isomer	MeSH
4-Methoxydalbergione, (S)-isomer	MeSH

Chemical Formula

C₁₆H₁₄O₃

Average Mass

254.2850 Da

Monoisotopic Mass

254.09429 Da

IUPAC Name

2-methoxy-5-[(1R)-1-phenylprop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione

Traditional Name

(R)-4-methoxydalbergione

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)C(=CC1=O)[C@H](C=C)C1=CC=CC=C1

InChI Identifier

InChI=1S/C16H14O3/c1-3-12(11-7-5-4-6-8-11)13-9-15(18)16(19-2)10-14(13)17/h3-10,12H,1H2,2H3/t12-/m1/s1

InChI Key

RGSUZUQISVAJJF-GFCCVEGCSA-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

Species Name	Source	Reference
Dalbergia cochinchinensis	LOTUS Database	35616633
Dalbergia latifolia	LOTUS Database	35616633
Dalbergia nigra	Plant	KNApSAcK
Dalbergia odorifera	LOTUS Database	35616633
Dalbergia parviflora	LOTUS Database	35616633
Dalbergia retusa	Plant	KNApSAcK
Dalbergia spp.	Plant	KNApSAcK
Ranunculus repens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dalbergiones. These are quinone derivatives containing a dalbergione moiety, which consists of a 1-4 quinone conjugated to a phenyl group at ring carbon 2.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Neoflavonoids

Sub Class

Dalbergiones

Direct Parent

Dalbergiones

Alternative Parents

Substituents

Dalbergione skeleton
Quinone
P-benzoquinone
Benzenoid
Monocyclic benzene moiety
Vinylogous ester
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

quinone (CHEBI:66703 )
enol ether (CHEBI:66703 )
Biflavonoids and polyflavonoids (C10505 )
Neoflavonoids (C10505 )
Neoflavonoids (LMPK12100072 )

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	2.65	ALOGPS
logP	3.02	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	75.99 m³·mol⁻¹	ChemAxon
Polarizability	26.71 Å³	ChemAxon
Number of Rings	2	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

C00002549

Chemspider ID

391131

KEGG Compound ID

C10505

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442809

PDB ID

Not Available

ChEBI ID

66703

Good Scents ID

Not Available

References

General References

Showing NP-Card for (R)-4-Methoxydalbergione (NP0051476)

MOL for NP0051476 ((R)-4-Methoxydalbergione)

3D MOL for NP0051476 ((R)-4-Methoxydalbergione)

3D SDF for NP0051476 ((R)-4-Methoxydalbergione)

3D-SDF for NP0051476 ((R)-4-Methoxydalbergione)

PDB for NP0051476 ((R)-4-Methoxydalbergione)

3D PDB for NP0051476 ((R)-4-Methoxydalbergione)

SMILES for NP0051476 ((R)-4-Methoxydalbergione)

INCHI for NP0051476 ((R)-4-Methoxydalbergione)

Structure for NP0051476 ((R)-4-Methoxydalbergione)

3D Structure for NP0051476 ((R)-4-Methoxydalbergione)