NP-MRD: Showing NP-Card for (S)-4,4'-Dimethoxydalbergione (NP0057207)

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Record Information

Version

2.0

Created at

2022-04-28 02:42:35 UTC

Updated at

2022-04-28 02:42:35 UTC

NP-MRD ID

NP0057207

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(S)-4,4'-Dimethoxydalbergione

Description

(S)-4,4'-dimethoxydalbergione 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, (S)-4,4'-dimethoxydalbergione is considered to be a flavonoid. (S)-4,4'-Dimethoxydalbergione is found in Dalbergia spp. Based on a literature review very few articles have been published on (s)-4,4'-dimethoxydalbergione.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.7906   -3.4682   -0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902   -2.8956    0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0064   -1.5610    0.9066 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1859   -0.8774    0.4142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1370   -0.4768    1.2774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3489    0.2116    0.8539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2375    0.5848    1.6616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5574    0.4878   -0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6968    1.1397   -0.9937 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8892    2.5413   -0.7609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6558    0.1166   -1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4434   -0.5772   -0.9870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6009   -0.9231   -1.8525 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2770   -0.8209    0.7296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3632    0.3996    0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5773    1.0674   -0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7369    0.4887    0.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9576    1.1214    0.2671 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9818    2.3763   -0.3811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6748   -0.7403    1.0438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4685   -1.3613    1.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7877   -3.0333   -0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6364   -4.4357   -0.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1474   -3.3518    0.2926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1087   -1.8389    1.9791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9577   -0.6928    2.3165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8751    2.6760    0.3346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7976    2.9018   -1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0268    3.0757   -1.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8068    0.3208   -2.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5028    0.9235   -0.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6148    2.0346   -0.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0433    2.7436   -0.2923 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2678    3.0334    0.1475 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6707    2.3090   -1.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5997   -1.1740    1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4599   -2.3254    1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 21  1  0
 21 20  2  0
 14  3  1  0
  3  2  1  0
  2  1  2  3
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 20 17  1  0
 12  4  1  0
 19 33  1  0
 19 34  1  0
 19 35  1  0
 16 32  1  0
 15 31  1  0
 21 37  1  0
 20 36  1  0
  3 25  1  1
  2 24  1  0
  1 22  1  0
  1 23  1  0
  5 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
M  END

  Mrv1652304282204422D          

 21 22  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  1  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
   -0.7145   -5.3625    0.0000 O   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
    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  1  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
 15 18  1  0  0  0  0
 18 19  1  0  0  0  0
  1 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057207

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O4/c1-4-13(11-5-7-12(20-2)8-6-11)14-9-16(19)17(21-3)10-15(14)18/h4-10,13H,1H2,2-3H3/t13-/m0/s1

> <INCHI_KEY>
FSNITHOUQGJHTR-ZDUSSCGKSA-N

> <FORMULA>
C17H16O4

> <MOLECULAR_WEIGHT>
284.311

> <EXACT_MASS>
284.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
29.758712221369528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-5-[(1S)-1-(4-methoxyphenyl)prop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.862135155666666

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.577617344476469

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
82.4574

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-4,4'-dimethoxydalbergione

> <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      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2    7   20                                                  
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   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15   19                                                       
CONECT   19   18                                                            
CONECT   20    1   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₄

Average Mass

284.3110 Da

Monoisotopic Mass

284.10486 Da

IUPAC Name

2-methoxy-5-[(1S)-1-(4-methoxyphenyl)prop-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione

Traditional Name

(S)-4,4'-dimethoxydalbergione

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C17H16O4/c1-4-13(11-5-7-12(20-2)8-6-11)14-9-16(19)17(21-3)10-15(14)18/h4-10,13H,1H2,2-3H3/t13-/m0/s1

InChI Key

FSNITHOUQGJHTR-ZDUSSCGKSA-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 spp.	Plant	KNApSAcK

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
Anisole
Phenoxy compound
P-benzoquinone
Phenol ether
Quinone
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous ester
Cyclic ketone
Ketone
Ether
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Neoflavonoids (LMPK12100074 )

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	2.51	ALOGPS
logP	2.86	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.46 m³·mol⁻¹	ChemAxon
Polarizability	29.76 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

C00010254

Chemspider ID

152481

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

174861

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (S)-4,4'-Dimethoxydalbergione (NP0057207)

MOL for NP0057207 ((S)-4,4'-Dimethoxydalbergione)

3D MOL for NP0057207 ((S)-4,4'-Dimethoxydalbergione)

3D SDF for NP0057207 ((S)-4,4'-Dimethoxydalbergione)

3D-SDF for NP0057207 ((S)-4,4'-Dimethoxydalbergione)

PDB for NP0057207 ((S)-4,4'-Dimethoxydalbergione)

3D PDB for NP0057207 ((S)-4,4'-Dimethoxydalbergione)

SMILES for NP0057207 ((S)-4,4'-Dimethoxydalbergione)

INCHI for NP0057207 ((S)-4,4'-Dimethoxydalbergione)

Structure for NP0057207 ((S)-4,4'-Dimethoxydalbergione)

3D Structure for NP0057207 ((S)-4,4'-Dimethoxydalbergione)