NP-MRD: Showing NP-Card for 3,6,7-trimethoxy-2-phenylchromen-4-one (NP0246906)

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Record Information

Version

2.0

Created at

2022-09-07 08:31:35 UTC

Updated at

2022-09-07 08:31:35 UTC

NP-MRD ID

NP0246906

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,6,7-trimethoxy-2-phenylchromen-4-one

Description

3,6,7-Trimethoxyflavone 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. 3,6,7-trimethoxy-2-phenylchromen-4-one was first documented in 2012 (PMID: 22799090). Based on a literature review a small amount of articles have been published on 3,6,7-trimethoxyflavone (PMID: 30384535) (PMID: 30520588) (PMID: 30088885) (PMID: 26411006).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    3.7315   -1.7683    3.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9837   -1.0706    2.0066 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0087   -0.5510    1.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6713   -0.6503    1.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7402   -0.1036    0.4898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5329   -0.2077    0.7082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4703    0.2999   -0.1142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8631    0.1103    0.2548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464    0.7161   -0.2953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2589    0.4330    0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5008   -0.4857    1.0772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4319   -1.1154    1.6554 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1482   -0.8343    1.2645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    0.9489   -1.2258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    1.4957   -2.1327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926    0.6018   -3.2164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3287    1.1014   -1.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6714    1.7094   -2.5614 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2069    0.5524   -0.6289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5573    0.6503   -0.8388 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4794    0.1131    0.0335 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8136    0.2489   -0.2396 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2480    0.9270   -1.3944 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7594   -1.5107    3.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7738   -2.8663    2.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5762   -1.6265    3.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115   -1.1695    2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8010    1.4717   -1.0501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0683    0.9445   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5022   -0.7432    1.4213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6037   -1.8574    2.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3103   -1.3464    1.7359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2975   -0.4407   -2.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2888    0.8599   -3.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5295    0.6894   -4.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8755    1.1796   -1.7393 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3581    0.8926   -1.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8819    1.9824   -1.3516 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8540    0.4193   -2.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 21  2  0
 21 22  1  0
 22 23  1  0
 21 20  1  0
 20 19  2  0
 19 17  1  0
 17 18  2  0
 17 14  1  0
 14 15  1  0
 15 16  1  0
 14  7  2  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  4  3  1  0
 13  8  1  0
  5 19  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
 23 37  1  0
 23 38  1  0
 23 39  1  0
 20 36  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
  4 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
M  END


  Mrv1652309072210312D          

 23 25  0  0  0  0            999 V2000
   -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 O   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    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 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
    4.2868   -0.0000    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
    5.0013    1.2375    0.0000 C   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
    5.7158   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
    4.2868   -2.4750    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
    2.8579   -2.4750    0.0000 O   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 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 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
  7 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
  3 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246906

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2C(=O)C(OC)=C(OC2=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O5/c1-20-14-9-12-13(10-15(14)21-2)23-17(18(22-3)16(12)19)11-7-5-4-6-8-11/h4-10H,1-3H3

> <INCHI_KEY>
KQNCAPDRHYRSCV-UHFFFAOYSA-N

> <FORMULA>
C18H16O5

> <MOLECULAR_WEIGHT>
312.321

> <EXACT_MASS>
312.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.838096094944774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6,7-trimethoxy-2-phenyl-4H-chromen-4-one

> <JCHEM_LOGP>
2.5180456086666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.415892439256992

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
86.61619999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,6,7-trimethoxy-2-phenylchromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -0.770   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  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -2.310   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  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    7   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    5   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    3   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₅

Average Mass

312.3210 Da

Monoisotopic Mass

312.09977 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C2C(=O)C(OC)=C(OC2=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C18H16O5/c1-20-14-9-12-13(10-15(14)21-2)23-17(18(22-3)16(12)19)11-7-5-4-6-8-11/h4-10H,1-3H3

InChI Key

KQNCAPDRHYRSCV-UHFFFAOYSA-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

Not Available

Chemical Taxonomy

Description

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

3-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
Flavone
3-methoxychromone
Chromone
Benzopyran
1-benzopyran
Anisole
Pyranone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00004586

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

129711225

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chen HY, Tu LF, Xiao CR, Luo YM: [Chemical constituents from fruits of Vitex trifolia var. simplicifolia]. Zhongguo Zhong Yao Za Zhi. 2018 Sep;43(18):3694-3700. doi: 10.19540/j.cnki.cjcmm.20180625.002. [PubMed:30384535 ]
Wang M, Xu GB, Liu J, Zhanga YH, Liu JH, Li J, Zhou M, Xiao YH, He X, Liao SG: Buxusoside, a Flavonoid Disaccharide from Buxus sinica. Nat Prod Commun. 2017 Apr;12(4):525-526. [PubMed:30520588 ]
Zhao XM, Li N, Du CX: [Chemical Constituents of Lowering LDL-C in Effective Part of Oroxylum indicum]. Zhong Yao Cai. 2016 Mar;39(3):555-8. [PubMed:30088885 ]
Diaz O, Alarcon R, Gutierrez D, Pacciaroni A, Cayo F, Sosa V: 6-Methoxyflavonoids and Other Constituents from Microliabum polymnioides (Asteraceae). Nat Prod Commun. 2015 Jul;10(7):1183-4. [PubMed:26411006 ]
Hussain J, Begum N, Hussain H, Khan FU, Rehman NU, Al-Harrasi A, Ali L: Ajuganane: a new phenolic compound from Ajuga bracteosa. Nat Prod Commun. 2012 May;7(5):615-6. [PubMed:22799090 ]
LOTUS database [Link]

Showing NP-Card for 3,6,7-trimethoxy-2-phenylchromen-4-one (NP0246906)

MOL for NP0246906 (3,6,7-trimethoxy-2-phenylchromen-4-one)

3D MOL for NP0246906 (3,6,7-trimethoxy-2-phenylchromen-4-one)

3D SDF for NP0246906 (3,6,7-trimethoxy-2-phenylchromen-4-one)

3D-SDF for NP0246906 (3,6,7-trimethoxy-2-phenylchromen-4-one)

PDB for NP0246906 (3,6,7-trimethoxy-2-phenylchromen-4-one)

3D PDB for NP0246906 (3,6,7-trimethoxy-2-phenylchromen-4-one)

SMILES for NP0246906 (3,6,7-trimethoxy-2-phenylchromen-4-one)

INCHI for NP0246906 (3,6,7-trimethoxy-2-phenylchromen-4-one)

Structure for NP0246906 (3,6,7-trimethoxy-2-phenylchromen-4-one)

3D Structure for NP0246906 (3,6,7-trimethoxy-2-phenylchromen-4-one)