NP-MRD: Showing NP-Card for 2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol (NP0224736)

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Record Information

Version

2.0

Created at

2022-09-06 03:14:40 UTC

Updated at

2022-09-06 03:14:41 UTC

NP-MRD ID

NP0224736

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol

Description

4'-O-Methylcatechin 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. 4'-O-Methylcatechin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4'-O-Methylcatechin has been detected, but not quantified in, chinese cinnamons and herbs and spices. 2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol is found in Cinnamomum aromaticum. This could make 4'-O-methylcatechin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305252D          

 22 24  0  0  0  0            999 V2000
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    1.4289   -1.6500    0.0000 C   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
    4.2868   -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
    2.1434   -0.4125    0.0000 C   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
    5.7158   -1.6500    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
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   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
  3  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  4  1  0  0  0  0
 13  7  1  0  0  0  0
 14  3  1  0  0  0  0
 14 12  2  0  0  0  0
 15  6  2  0  0  0  0
 15 10  1  0  0  0  0
 16  8  1  0  0  0  0
 16 13  1  0  0  0  0
 17  9  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21  1  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224736

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(C=C1)C1OC2=CC(O)=CC(O)=C2CC1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O6/c1-21-14-3-2-8(4-12(14)19)16-13(20)7-10-11(18)5-9(17)6-15(10)22-16/h2-6,13,16-20H,7H2,1H3

> <INCHI_KEY>
ZHDMPVIDHWJGTN-UHFFFAOYSA-N

> <FORMULA>
C16H16O6

> <MOLECULAR_WEIGHT>
304.2946

> <EXACT_MASS>
304.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
30.28598518688749

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
1.941001071333333

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.904755679630084

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.273445507560783

> <JCHEM_PKA_STRONGEST_BASIC>
-3.290208980895425

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
78.48200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <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      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -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       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    8                                                       
CONECT    3    2   14                                                       
CONECT    4    8   12                                                       
CONECT    5    9   11                                                       
CONECT    6    9   15                                                       
CONECT    7   10   13                                                       
CONECT    8    2    4   16                                                  
CONECT    9    5    6   17                                                  
CONECT   10    7   11   15                                                  
CONECT   11    5   10   18                                                  
CONECT   12    4   14   19                                                  
CONECT   13    7   16   20                                                  
CONECT   14    3   12   21                                                  
CONECT   15    6   10   22                                                  
CONECT   16    8   13   22                                                  
CONECT   17    9                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21    1   14                                                       
CONECT   22   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
3,3',5,7-Tetrahydroxy-4'-methoxyflavan	HMDB
Catechin 4'-methyl ether	HMDB

Chemical Formula

C₁₆H₁₆O₆

Average Mass

304.2946 Da

Monoisotopic Mass

304.09469 Da

IUPAC Name

2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(C=C1)C1OC2=CC(O)=CC(O)=C2CC1O

InChI Identifier

InChI=1S/C16H16O6/c1-21-14-3-2-8(4-12(14)19)16-13(20)7-10-11(18)5-9(17)6-15(10)22-16/h2-6,13,16-20H,7H2,1H3

InChI Key

ZHDMPVIDHWJGTN-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	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
4p-methoxyflavonoid-skeleton
3'-hydroxyflavonoid
3-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Polyol
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen 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	1.31	ALOGPS
logP	1.94	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.27	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.48 m³·mol⁻¹	ChemAxon
Polarizability	30.29 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

HMDB0030662

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002573

KNApSAcK ID

C00008810

Chemspider ID

13077666

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14332897

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol (NP0224736)

MOL for NP0224736 (2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

3D MOL for NP0224736 (2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

3D SDF for NP0224736 (2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

3D-SDF for NP0224736 (2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

PDB for NP0224736 (2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

3D PDB for NP0224736 (2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

SMILES for NP0224736 (2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

INCHI for NP0224736 (2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

Structure for NP0224736 (2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)

3D Structure for NP0224736 (2-(3-hydroxy-4-methoxyphenyl)-3,4-dihydro-2h-1-benzopyran-3,5,7-triol)