NP-MRD: Showing NP-Card for 3,4-Methylenedioxy-2',4'-dimethoxychalcone (NP0060632)

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Record Information

Version

2.0

Created at

2022-04-28 05:38:57 UTC

Updated at

2022-04-28 05:38:57 UTC

NP-MRD ID

NP0060632

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-Methylenedioxy-2',4'-dimethoxychalcone

Description

3,4-Methylenedioxy-2',4'-dimethoxychalcone, also known as 3,4-MD-DMC, belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid. Thus, 3,4-methylenedioxy-2',4'-dimethoxychalcone is considered to be a flavonoid. 3,4-Methylenedioxy-2',4'-dimethoxychalcone is found in Millettia erythrocalyx. 3,4-Methylenedioxy-2',4'-dimethoxychalcone was first documented in 2002 (PMID: 12453522). Based on a literature review very few articles have been published on 3,4-Methylenedioxy-2',4'-dimethoxychalcone.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -6.4750    1.7138   -0.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0063    0.6259   -1.0619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7043    0.1823   -1.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3379   -0.8932   -1.8196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0375   -1.3254   -1.8022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0248   -0.7374   -1.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6774   -1.2659   -1.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5012   -2.2692   -1.8497 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530   -0.7548   -0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6458   -1.3448   -0.4961 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8273   -0.8975    0.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8656    0.1488    1.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0582    0.5149    1.6888 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2294   -0.1631    1.4711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2021   -1.2263    0.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0313   -1.5748   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5056   -1.7407    0.5554 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3703   -0.7735    1.1213 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5354   -0.0044    1.9680 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4035    0.3399   -0.2765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4811    1.0062    0.5226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8983    2.1020    1.2911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7369    0.7807   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6945    1.3842    0.7350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4384    2.0393   -0.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7698    2.5752   -0.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0964   -1.3973   -2.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7829   -2.1870   -2.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4474    0.0771    0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7096   -2.2012   -1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0237    0.7417    1.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0928    1.3524    2.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0734   -2.4321   -0.6902 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1593   -1.2188    1.7565 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8510   -0.1303    0.3776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3393    2.9204    0.6516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0167    2.5548    1.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6843    1.8463    2.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9746    1.6317    0.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 23  2  0
 23 20  1  0
 20 21  1  0
 21 22  1  0
 20  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 19  1  0
 19 18  1  0
 18 17  1  0
 17 15  1  0
 15 16  2  0
  4  3  1  0
 16 11  1  0
 15 14  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 23 39  1  0
 22 36  1  0
 22 37  1  0
 22 38  1  0
  5 28  1  0
  4 27  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 13 32  1  0
 18 34  1  0
 18 35  1  0
 16 33  1  0
M  END


  Mrv1652304282207392D          

 23 25  0  0  0  0            999 V2000
    5.4957    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.0604    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060632

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C(C=C1)C(=O)\C=C\C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O5/c1-20-13-5-6-14(17(10-13)21-2)15(19)7-3-12-4-8-16-18(9-12)23-11-22-16/h3-10H,11H2,1-2H3/b7-3+

> <INCHI_KEY>
XMQLRMQKCIIQEY-XVNBXDOJSA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.321

> <EXACT_MASS>
312.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
33.132028827230386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(2H-1,3-benzodioxol-5-yl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
3.1982162453333336

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.60761240791754

> <JCHEM_PKA_STRONGEST_BASIC>
-4.34386325543276

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
85.57030000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.60e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(2H-1,3-benzodioxol-5-yl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one

> <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      10.259   9.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.592   8.233   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.592   6.693   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.259   5.923   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.592   3.613   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.926   5.923   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      12.926   4.383   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      10.259  10.543   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.925  11.313   0.000  0.00  0.00           C+0
CONECT    1    2    6   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   11                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    3   21                                                       
CONECT   21   20                                                            
CONECT   22    1   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
3,4-MD-DMC	MeSH

Chemical Formula

C₁₈H₁₆O₅

Average Mass

312.3210 Da

Monoisotopic Mass

312.09977 Da

IUPAC Name

(2E)-3-(2H-1,3-benzodioxol-5-yl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one

Traditional Name

(2E)-3-(2H-1,3-benzodioxol-5-yl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C(C=C1)C(=O)\C=C\C1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C18H16O5/c1-20-13-5-6-14(17(10-13)21-2)15(19)7-3-12-4-8-16-18(9-12)23-11-22-16/h3-10H,11H2,1-2H3/b7-3+

InChI Key

XMQLRMQKCIIQEY-XVNBXDOJSA-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
Millettia erythrocalyx	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acids and derivatives. These are organic aromatic compounds containing a benzene and a carboxylic acid group (or a derivative thereof) forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Not Available

Direct Parent

Cinnamic acids and derivatives

Alternative Parents

Substituents

Cinnamic acid or derivatives
Dimethoxybenzene
M-dimethoxybenzene
Benzodioxole
Methoxybenzene
Anisole
Benzoyl
Phenoxy compound
Aryl ketone
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Alpha,beta-unsaturated ketone
Enone
Ketone
Organoheterocyclic compound
Acetal
Oxacycle
Ether
Aldehyde
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120117 )

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	3.31	ALOGPS
logP	3.2	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	16.61	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.57 m³·mol⁻¹	ChemAxon
Polarizability	33.13 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00014427

Chemspider ID

4477881

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319619

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sritularak B, Likhitwitayawuid K, Conrad J, Kraus W: Flavonoids from the roots of Millettia erythrocalyx. Phytochemistry. 2002 Dec;61(8):943-7. doi: 10.1016/s0031-9422(02)00337-0. [PubMed:12453522 ]

Showing NP-Card for 3,4-Methylenedioxy-2',4'-dimethoxychalcone (NP0060632)

MOL for NP0060632 (3,4-Methylenedioxy-2',4'-dimethoxychalcone)

3D MOL for NP0060632 (3,4-Methylenedioxy-2',4'-dimethoxychalcone)

3D SDF for NP0060632 (3,4-Methylenedioxy-2',4'-dimethoxychalcone)

3D-SDF for NP0060632 (3,4-Methylenedioxy-2',4'-dimethoxychalcone)

PDB for NP0060632 (3,4-Methylenedioxy-2',4'-dimethoxychalcone)

3D PDB for NP0060632 (3,4-Methylenedioxy-2',4'-dimethoxychalcone)

SMILES for NP0060632 (3,4-Methylenedioxy-2',4'-dimethoxychalcone)

INCHI for NP0060632 (3,4-Methylenedioxy-2',4'-dimethoxychalcone)

Structure for NP0060632 (3,4-Methylenedioxy-2',4'-dimethoxychalcone)

3D Structure for NP0060632 (3,4-Methylenedioxy-2',4'-dimethoxychalcone)