NP-MRD: Showing NP-Card for (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin (NP0048950)

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Record Information

Version

2.0

Created at

2022-03-17 21:04:44 UTC

Updated at

2022-03-17 21:04:44 UTC

NP-MRD ID

NP0048950

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin

Description

(±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin, also known as 3',4'-methylenedioxy epicatechin 5,7-dimethyl ether, belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin has been detected, but not quantified in, chinese cinnamons and herbs and spices. (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin is found in Cinnamomum camphora and Persea sp.. This could make (±)-3',4'-methylenedioxy-5,7-dimethylepicatechin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310072D          

 24 27  0  0  0  0            999 V2000
    7.0714    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    3.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6424    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3569    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    4.6654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    3.3305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
 10  3  1  0  0  0  0
 10  5  2  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  8  1  0  0  0  0
 14  4  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  2  0  0  0  0
 16  7  2  0  0  0  0
 16 12  1  0  0  0  0
 17  5  1  0  0  0  0
 17 14  2  0  0  0  0
 18 10  1  0  0  0  0
 18 13  1  0  0  0  0
 19 13  1  0  0  0  0
 20  1  1  0  0  0  0
 20 11  1  0  0  0  0
 21  2  1  0  0  0  0
 21 15  1  0  0  0  0
 22  9  1  0  0  0  0
 22 14  1  0  0  0  0
 23  9  1  0  0  0  0
 23 17  1  0  0  0  0
 24 16  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048950

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2CC(O)C(OC2=C1)C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O6/c1-20-11-6-15(21-2)12-8-13(19)18(24-16(12)7-11)10-3-4-14-17(5-10)23-9-22-14/h3-7,13,18-19H,8-9H2,1-2H3

> <INCHI_KEY>
MMKQEVQTCAAXTI-UHFFFAOYSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.3319

> <EXACT_MASS>
330.110338308

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
33.96530531278701

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2H-1,3-benzodioxol-5-yl)-5,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-3-ol

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.3172592383333335

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.867563940924796

> <JCHEM_PKA_STRONGEST_BASIC>
-3.294127532239494

> <JCHEM_POLAR_SURFACE_AREA>
66.38000000000001

> <JCHEM_REFRACTIVITY>
84.7694

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2H-1,3-benzodioxol-5-yl)-5,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      13.200   5.923   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.865   1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.864   8.233   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.530   9.003   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530   5.923   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.532   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.199   6.693   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.173   7.463   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.864   6.693   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.532   5.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.865   4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   8.233   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.199   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.865   5.923   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.198   5.923   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.864   3.613   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.866   6.693   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.199   2.073   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -0.268   8.709   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.268   6.217   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.531   6.693   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    4   10                                                       
CONECT    4    3   14                                                       
CONECT    5   10   17                                                       
CONECT    6   11   15                                                       
CONECT    7   11   16                                                       
CONECT    8   12   13                                                       
CONECT    9   22   23                                                       
CONECT   10    3    5   18                                                  
CONECT   11    6    7   20                                                  
CONECT   12    8   15   16                                                  
CONECT   13    8   18   19                                                  
CONECT   14    4   17   22                                                  
CONECT   15    6   12   21                                                  
CONECT   16    7   12   24                                                  
CONECT   17    5   14   23                                                  
CONECT   18   10   13   24                                                  
CONECT   19   13                                                            
CONECT   20    1   11                                                       
CONECT   21    2   15                                                       
CONECT   22    9   14                                                       
CONECT   23    9   17                                                       
CONECT   24   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
3',4'-Methylenedioxy epicatechin 5,7-dimethyl ether	HMDB

Chemical Formula

C₁₈H₁₈O₆

Average Mass

330.3319 Da

Monoisotopic Mass

330.11034 Da

IUPAC Name

2-(2H-1,3-benzodioxol-5-yl)-5,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-3-ol

Traditional Name

2-(2H-1,3-benzodioxol-5-yl)-5,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-3-ol

CAS Registry Number

87562-72-9

SMILES

COC1=CC(OC)=C2CC(O)C(OC2=C1)C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C18H18O6/c1-20-11-6-15(21-2)12-8-13(19)18(24-16(12)7-11)10-3-4-14-17(5-10)23-9-22-14/h3-7,13,18-19H,8-9H2,1-2H3

InChI Key

MMKQEVQTCAAXTI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cinnamomum aromaticum	FooDB	KNAPSACK
Cinnamomum camphora	LOTUS Database	35616633
Persea sp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
5-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
3-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Secondary alcohol
Ether
Organoheterocyclic compound
Acetal
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.36	ALOGPS
logP	2.32	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.87	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.77 m³·mol⁻¹	ChemAxon
Polarizability	33.97 Å³	ChemAxon
Number of Rings	4	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

HMDB0037955

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017127

KNApSAcK ID

C00008829

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

71307295

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin (NP0048950)

MOL for NP0048950 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

3D MOL for NP0048950 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

3D SDF for NP0048950 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

3D-SDF for NP0048950 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

PDB for NP0048950 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

3D PDB for NP0048950 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

SMILES for NP0048950 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

INCHI for NP0048950 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

Structure for NP0048950 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)

3D Structure for NP0048950 ((±)-3',4'-Methylenedioxy-5,7-dimethylepicatechin)