NP-MRD: Showing NP-Card for 2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one (NP0332792)

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Record Information

Version

2.0

Created at

2024-04-20 01:33:56 UTC

Updated at

2024-09-03 04:20:19 UTC

NP-MRD ID

NP0332792

Natural Product DOI

https://doi.org/10.57994/2063

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one

Description

2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one is also known as 5-hydroxy-7,4'-dimethoxyflavanone or 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one. 2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one was first documented in 2011 (PMID: 21859261). Based on a literature review a small amount of articles have been published on 2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one (PMID: 22899281) (PMID: 29090551) (PMID: 22737859) (PMID: 30971246).

Structure

MOL SDF PDB SMILES InChI

  Mrv2104 01022304102D          

 22 24  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 O   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
    2.1434   -0.4125    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
    2.8579    0.8250    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   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
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 O   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
    0.0000   -2.4750    0.0000 C   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   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    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
   -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
  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
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
  3 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 14 21  1  0  0  0  0
 13 22  1  0  0  0  0
  2 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0332792

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(OC)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1/C17H16O5/c1-20-11-5-3-10(4-6-11)15-9-14(19)17-13(18)7-12(21-2)8-16(17)22-15/h3-8,15,18H,9H2,1-2H3

> <INCHI_KEY>
CKEXCBVNKRHAMX-UHFFFAOYNA-N

> <FORMULA>
C17H16O5

> <MOLECULAR_WEIGHT>
300.31

> <EXACT_MASS>
300.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.516495776878024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.126896162333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.767401896524785

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.690532705938551

> <JCHEM_PKA_STRONGEST_BASIC>
-4.397738615607933

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
80.25440000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
naringenin 7,4'-dimethyl ether

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-JAN-23         0                                  
HETATM    1  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10    3   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20   17   21                                                       
CONECT   21   20   14                                                       
CONECT   22   13    2                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
5-Hydroxy-2,3-dihydro-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
5-Hydroxy-7,4'-dimethoxyflavanone	ChEBI
5-Hydroxy-7-methoxy-2-(4-methoxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one	ChEBI
5-Hydroxy-7-methoxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one	ChEBI
7,4'-Dimethoxy-5-hydroxyflavanone	ChEBI
Naringenin 7,4'-dimethyl ether	ChEBI

Chemical Formula

C₁₇H₁₆O₅

Average Mass

300.3100 Da

Monoisotopic Mass

300.09977 Da

IUPAC Name

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

Traditional Name

naringenin 7,4'-dimethyl ether

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1CC(=O)C2=C(O)C=C(OC)C=C2O1

InChI Identifier

InChI=1/C17H16O5/c1-20-11-5-3-10(4-6-11)15-9-14(19)17-13(18)7-12(21-2)8-16(17)22-15/h3-8,15,18H,9H2,1-2H3

InChI Key

CKEXCBVNKRHAMX-UHFFFAOYNA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental)	Not Available	Not Available	liulianbanxiangcai	2024-04-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental)	Not Available	Not Available	liulianbanxiangcai	2024-04-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anisomeles indica		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

4p-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
5-hydroxyflavonoid
Flavanone
Hydroxyflavonoid
Flavan
Chromone
Benzopyran
Chromane
1-benzopyran
Phenoxy compound
Methoxybenzene
Anisole
Phenol ether
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140574 )

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	3.13	ChemAxon
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.25 m³·mol⁻¹	ChemAxon
Polarizability	31.52 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

C00008226

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

Not Available

PDB ID

Not Available

ChEBI ID

157737

Good Scents ID

Not Available

References

General References

Kouame PB, Jacques C, Bedi G, Silvestre V, Loquet D, Barille-Nion S, Robins RJ, Tea I: Phytochemicals isolated from leaves of Chromolaena odorata: impact on viability and clonogenicity of cancer cell lines. Phytother Res. 2013 Jun;27(6):835-40. doi: 10.1002/ptr.4787. Epub 2012 Aug 16. [PubMed:22899281 ]
Chen YM, Cao NK, Tu PF, Jiang Y: [Chemical constituents from Murraya euchrestifolia]. Zhongguo Zhong Yao Za Zhi. 2017 May;42(10):1916-1921. doi: 10.19540/j.cnki.cjcmm.20170228.002. [PubMed:29090551 ]
Thuy TT, Quan TD, Anh NT, Van Sung T: A new hydrochalcone from Miliusa sinensis. Nat Prod Res. 2011 Aug;25(14):1361-5. doi: 10.1080/14786419.2011.569505. [PubMed:21859261 ]
Zhang J, Li L, Liu X, Wang Y, Zhao D: [Study on chemical constituents of Artemisia sphaerocephala]. Zhongguo Zhong Yao Za Zhi. 2012 Jan;37(2):238-42. [PubMed:22737859 ]
Cui H, Song MC, Ban YH, Jun SY, Kwon AS, Lee JY, Yoon YJ: High-yield production of multiple O-methylated phenylpropanoids by the engineered Escherichia coli-Streptomyces cocultivation system. Microb Cell Fact. 2019 Apr 10;18(1):67. doi: 10.1186/s12934-019-1118-9. [PubMed:30971246 ]

Showing NP-Card for 2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one (NP0332792)

MOL for NP0332792 (2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one)

3D MOL for NP0332792 (2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one)

3D SDF for NP0332792 (2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one)

3D-SDF for NP0332792 (2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one)

PDB for NP0332792 (2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one)

3D PDB for NP0332792 (2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one)

SMILES for NP0332792 (2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one)

INCHI for NP0332792 (2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one)

Structure for NP0332792 (2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one)

3D Structure for NP0332792 (2,3-Dihydro-5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one)