NP-MRD: Showing NP-Card for 3-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan (NP0138463)

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Record Information

Version

1.0

Created at

2022-06-29 17:30:42 UTC

Updated at

2022-06-29 17:30:42 UTC

NP-MRD ID

NP0138463

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan

Description

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-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan is found in Cinnamomum camphora. Based on a literature review very few articles have been published on 3',4'-methylenedioxy epicatechin 5,7-dimethyl ether.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 45  0  0  0  0  0  0  0  0999 V2000
   -3.8356    3.9883   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0990    2.6263   -0.3814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2137    1.6069   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6538    0.3109   -0.2582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8188   -0.7729    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2295   -2.0720   -0.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5390   -2.4092   -0.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5240   -0.5355    0.4474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0509    0.7276    0.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9229    1.7702    0.3396 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454    0.9594    1.0584 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1244   -0.1178    1.4421 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2263   -0.2898    0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5895   -1.5002    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6541   -1.6648   -0.8817 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3900   -0.5752   -1.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0386    0.6570   -0.7843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9921    0.8066    0.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9372    1.5523   -1.3574 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0937    0.8021   -1.7319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4754   -0.4228   -2.1442 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3049   -1.2974    1.8000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0575   -2.3434    2.3018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6665   -1.7022    0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7771    4.5623   -0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1751    4.1462    0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3058    4.3838   -1.1584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6583    0.0946   -0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7726   -3.4741   -0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2574   -1.7642   -0.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5841   -2.1419   -1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5552    2.7719    0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    0.2647    2.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0557   -2.3887    0.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9036   -2.6489   -1.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7234    1.7810    0.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7720    0.6303   -0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5705    1.2257   -2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3827   -1.0213    2.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8058   -1.9407    2.8135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2429   -2.0361   -0.2138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2642   -2.5493    1.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 10  2  0
 10  9  1  0
  9  8  2  0
  8 24  1  0
 24 22  1  0
 22 23  1  0
 22 12  1  0
 12 11  1  0
 12 13  1  0
 13 18  2  0
 18 17  1  0
 17 16  2  0
 16 21  1  0
 21 20  1  0
 20 19  1  0
 16 15  1  0
 15 14  2  0
  8  5  1  0
  5  6  1  0
  6  7  1  0
  5  4  2  0
  4  3  1  0
 11  9  1  0
 14 13  1  0
 19 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 10 32  1  0
 24 41  1  0
 24 42  1  0
 22 39  1  1
 23 40  1  0
 12 33  1  1
 18 36  1  0
 20 37  1  0
 20 38  1  0
 15 35  1  0
 14 34  1  0
  7 29  1  0
  7 30  1  0
  7 31  1  0
  4 28  1  0
M  END


  Mrv1652306292219302D          

 24 27  0  0  1  0            999 V2000
   10.4970    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7825    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0681    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.9246    2.3479    0.0000 O   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
    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
    4.0668    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
    5.4957    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2821    3.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7972    2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2821    2.0930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0681    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3536   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0681   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 10  1  0  0  0  0
  9 11  1  1  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
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
  8 20  1  1  0  0  0
  6 21  1  0  0  0  0
 21 22  2  0  0  0  0
  3 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138463

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C[C@@H](O)[C@H](O2)C2=CC3=C(OCO3)C=C2)C(OC)=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/t13-,18-/m1/s1

> <INCHI_KEY>
MMKQEVQTCAAXTI-FZKQIMNGSA-N

> <FORMULA>
C18H18O6

> <MOLECULAR_WEIGHT>
330.336

> <EXACT_MASS>
330.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.05442575934868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-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>
84.76940000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      19.594   3.613   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      18.261   4.383   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      16.927   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.593   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.260   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.260   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.926   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.592   2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.592   3.613   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      12.926   4.383   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.259   4.383   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.925   6.693   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.259   5.923   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.127   6.399   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.221   5.153   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.127   3.907   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.259   1.303   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      15.593   1.303   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      16.927   2.073   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      15.593  -0.237   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      16.927  -1.007   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17   14   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   13                                                       
CONECT   20    8                                                            
CONECT   21    6   22   23                                                  
CONECT   22   21    3                                                       
CONECT   23   21   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈O₆

Average Mass

330.3360 Da

Monoisotopic Mass

330.11034 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

162602-04-2

SMILES

COC1=CC2=C(C[C@@H](O)[C@H](O2)C2=CC3=C(OCO3)C=C2)C(OC)=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/t13-,18-/m1/s1

InChI Key

MMKQEVQTCAAXTI-FZKQIMNGSA-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
Cinnamomum camphora	LOTUS Database	35616633

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

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020145 )

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008829

Chemspider ID

8512188

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10336729

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan (NP0138463)

MOL for NP0138463 (3-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan)

3D MOL for NP0138463 (3-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan)

3D SDF for NP0138463 (3-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan)

3D-SDF for NP0138463 (3-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan)

PDB for NP0138463 (3-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan)

3D PDB for NP0138463 (3-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan)

SMILES for NP0138463 (3-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan)

INCHI for NP0138463 (3-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan)

Structure for NP0138463 (3-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan)

3D Structure for NP0138463 (3-Hydroxy-5,7-dimethoxy-3',4'-methylenedioxyflavan)