NP-MRD: Showing NP-Card for Afzelechin 5,4'-dimethyl ether (NP0056071)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 01:57:14 UTC

Updated at

2022-04-28 01:57:15 UTC

NP-MRD ID

NP0056071

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Afzelechin 5,4'-dimethyl ether

Description

Afzelechin 5,4'-dimethyl ether belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone. Thus, afzelechin 5,4'-dimethyl ether is considered to be a flavonoid. Afzelechin 5,4'-dimethyl ether is found in Lagascea rigida. Based on a literature review very few articles have been published on Afzelechin 5,4'-dimethyl ether.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    6.1818   -0.0579   -1.7039 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2954   -0.9585   -1.1128 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1333   -0.6047   -0.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3504   -1.6052    0.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1618   -1.3254    0.7693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7379   -0.0361    0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5035    0.3720    1.6261 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1873    1.3451    0.8717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3776    1.1598    0.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0254    2.2534   -0.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2229    2.0815   -1.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9046    3.1522   -1.6333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7383    0.8036   -1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1082   -0.2804   -0.5064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6383   -1.5661   -0.5645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8596   -1.7428   -1.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9179   -0.1041    0.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2127   -1.2390    0.7783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4092   -0.7592    1.9674 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3546   -0.2573    2.8919 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221    0.9653    0.3874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7042    0.6941   -0.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2117   -0.4971   -1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0121    0.0715   -2.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2027    0.9040   -1.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6670   -2.6380   -0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5749   -2.1168    1.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7862    0.8702    2.5946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6210    3.2477   -0.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5866    3.6694   -1.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6843    0.6779   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6417   -1.1645   -0.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1195   -2.7998   -1.4065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7503   -1.2694   -2.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5969   -1.7384    0.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9302   -1.9943    1.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0799   -1.5967    2.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7514    0.5738    2.5894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2098    2.0137    0.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3040    1.4969   -0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 21  1  0
 21 22  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 22  3  1  0
 19  7  1  0
 17  9  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
 21 39  1  0
 22 40  1  0
  7 28  1  1
 10 29  1  0
 12 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 18 36  1  0
 19 37  1  1
 20 38  1  0
M  END

  Mrv1652304282203572D          

 22 24  0  0  1  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   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
  5  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
  4 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  6  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
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056071

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)[C@H]1OC2=CC(O)=CC(OC)=C2C[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H18O5/c1-20-12-5-3-10(4-6-12)17-14(19)9-13-15(21-2)7-11(18)8-16(13)22-17/h3-8,14,17-19H,9H2,1-2H3/t14-,17+/m0/s1

> <INCHI_KEY>
WKYDSIJBQQASGS-WMLDXEAASA-N

> <FORMULA>
C17H18O5

> <MOLECULAR_WEIGHT>
302.326

> <EXACT_MASS>
302.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
31.374345346765374

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S)-5-methoxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,7-diol

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
2.3904604490000003

> <ALOGPS_LOGS>
-3.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.931382160390271

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.74480448615909

> <JCHEM_PKA_STRONGEST_BASIC>
-3.286012721486185

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
80.9834

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
afzelechin 5,4'-dimethyl ether

> <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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   22                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9                                                            
CONECT   12    8   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    3   21                                                       
CONECT   21   20                                                            
CONECT   22    1                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₈O₅

Average Mass

302.3260 Da

Monoisotopic Mass

302.11542 Da

IUPAC Name

(2R,3S)-5-methoxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,7-diol

Traditional Name

afzelechin 5,4'-dimethyl ether

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)[C@H]1OC2=CC(O)=CC(OC)=C2C[C@@H]1O

InChI Identifier

InChI=1S/C17H18O5/c1-20-12-5-3-10(4-6-12)17-14(19)9-13-15(21-2)7-11(18)8-16(13)22-17/h3-8,14,17-19H,9H2,1-2H3/t14-,17+/m0/s1

InChI Key

WKYDSIJBQQASGS-WMLDXEAASA-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
Lagascea rigida	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C5 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

5-O-methylated flavonoids

Alternative Parents

Substituents

4p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
Flavan-3-ol
Hydroxyflavonoid
3-hydroxyflavonoid
7-hydroxyflavonoid
Flavan
1-benzopyran
Benzopyran
Chromane
Phenol ether
Phenoxy compound
Anisole
Methoxybenzene
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020138 )

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	2.23	ALOGPS
logP	2.39	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.74	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.98 m³·mol⁻¹	ChemAxon
Polarizability	31.37 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

C00008807

Chemspider ID

24842577

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257123

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Afzelechin 5,4'-dimethyl ether (NP0056071)

MOL for NP0056071 (Afzelechin 5,4'-dimethyl ether)

3D MOL for NP0056071 (Afzelechin 5,4'-dimethyl ether)

3D SDF for NP0056071 (Afzelechin 5,4'-dimethyl ether)

3D-SDF for NP0056071 (Afzelechin 5,4'-dimethyl ether)

PDB for NP0056071 (Afzelechin 5,4'-dimethyl ether)

3D PDB for NP0056071 (Afzelechin 5,4'-dimethyl ether)

SMILES for NP0056071 (Afzelechin 5,4'-dimethyl ether)

INCHI for NP0056071 (Afzelechin 5,4'-dimethyl ether)

Structure for NP0056071 (Afzelechin 5,4'-dimethyl ether)

3D Structure for NP0056071 (Afzelechin 5,4'-dimethyl ether)