NP-MRD: Showing NP-Card for 5,6,7-Trimethoxycoumarin (NP0051461)

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Record Information

Version

2.0

Created at

2022-04-27 22:49:11 UTC

Updated at

2022-04-27 22:49:11 UTC

NP-MRD ID

NP0051461

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6,7-Trimethoxycoumarin

Description

5,6,7-Trimethoxycoumarin, also known as fraxinol methyl ether, belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). 5,6,7-Trimethoxycoumarin is found in Aleurites cordata, Artemisia capillaris, Diosma pilosa, Pelargonium reniforme, Pelargonium sidoides , Rhododendron collettianum and Aleurites fordii. 5,6,7-Trimethoxycoumarin was first documented in 1997 (PMID: 9434601). 5,6,7-Trimethoxycoumarin is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 18058380) (PMID: 11295313) (PMID: 14661854) (PMID: 17613825).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    3.2846    1.2127    1.6318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6571    0.1091    1.0152 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3682    0.2514    0.5442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7333    1.4664    0.6902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5769    1.6015    0.2082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1778    2.7611    0.3497 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3999    2.9240   -0.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9563    4.0697    0.0669 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0718    1.8903   -0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4652    0.6732   -0.8574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1760    0.5084   -0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5388   -0.7170   -0.5421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2215   -1.7411   -1.1547 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0308   -2.6681   -0.4431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7392   -0.8269   -0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4245   -2.0125   -0.1809 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2271   -2.2844   -1.3316 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2436    2.0962    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7435    1.3992    2.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3497    0.9624    1.8187 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2111    2.3157    1.1628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0984    2.0291   -1.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9338   -0.1796   -1.3275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3774   -3.0530    0.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8925   -2.1560    0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3650   -3.4731   -1.1045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5674   -2.7644   -2.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013   -3.0032   -1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7313   -1.3911   -1.7116 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 11  2  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 12 15  2  0
 15 16  1  0
 16 17  1  0
 15  3  1  0
  6  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
 10 23  1  0
  9 22  1  0
 14 24  1  0
 14 25  1  0
 14 26  1  0
 17 27  1  0
 17 28  1  0
 17 29  1  0
M  END


  Mrv1533004241509062D          

 17 18  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 O   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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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
    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  5 11  2  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
 12 15  2  0  0  0  0
  3 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051461

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=CC(=O)O2)C(OC)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C12H12O5/c1-14-9-6-8-7(4-5-10(13)17-8)11(15-2)12(9)16-3/h4-6H,1-3H3

> <INCHI_KEY>
FOBNRKTURPWTQX-UHFFFAOYSA-N

> <FORMULA>
C12H12O5

> <MOLECULAR_WEIGHT>
236.223

> <EXACT_MASS>
236.068473486

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
23.17567976141844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,6,7-trimethoxy-2H-chromen-2-one

> <ALOGPS_LOGP>
1.79

> <JCHEM_LOGP>
1.310345818333333

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.454602954437557

> <JCHEM_POLAR_SURFACE_AREA>
53.99000000000001

> <JCHEM_REFRACTIVITY>
60.93820000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6,7-trimethoxycoumarin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         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  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -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  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   17  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   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12    3   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
5,6,7-Trimethoxy-2H-1-benzopyran-2-one	ChEBI
Fraxinol methyl ether	ChEBI

Chemical Formula

C₁₂H₁₂O₅

Average Mass

236.2230 Da

Monoisotopic Mass

236.06847 Da

IUPAC Name

5,6,7-trimethoxy-2H-chromen-2-one

Traditional Name

5,6,7-trimethoxycoumarin

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=CC(=O)O2)C(OC)=C1OC

InChI Identifier

InChI=1S/C12H12O5/c1-14-9-6-8-7(4-5-10(13)17-8)11(15-2)12(9)16-3/h4-6H,1-3H3

InChI Key

FOBNRKTURPWTQX-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, 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
Aleurites cordata	Plant	KNApSAcK
Artemisia capillaris	LOTUS Database	35616633
Diosma pilosa	Plant	KNApSAcK
Pelargonium reniforme	Plant	KNApSAcK
Pelargonium sidoides	Plant	KNApSAcK
Rhododendron collettianum	Plant	KNApSAcK
Vernicia fordii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:28126 )
coumarins (CHEBI:28126 )
coumarins (C09313 )

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	1.79	ALOGPS
logP	1.31	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	60.94 m³·mol⁻¹	ChemAxon
Polarizability	23.18 Å³	ChemAxon
Number of Rings	2	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

C00002501

Chemspider ID

Not Available

KEGG Compound ID

C09313

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

148724

PDB ID

Not Available

ChEBI ID

28126

Good Scents ID

Not Available

References

General References

Saeed MA, Sabir AW: Irritant and cytotoxic coumarins from Angelica glauca Edgew roots. J Asian Nat Prod Res. 2008 Jan-Feb;10(1-2):49-58. doi: 10.1080/10286020701273759. [PubMed:18058380 ]
Satyanarayana P, Kumar KA, Singh SK, Rao GN: A new phorbol diester from Aleurites moluccana. Fitoterapia. 2001 Mar;72(3):304-6. doi: 10.1016/s0367-326x(00)00314-2. [PubMed:11295313 ]
Lee S, Kim KS, Shim SH, Park YM, Kim BK: Constituents from the non-polar fraction of Artemisia apiacea. Arch Pharm Res. 2003 Nov;26(11):902-5. doi: 10.1007/BF02980197. [PubMed:14661854 ]
Uddin SJ, Shilpi JA, Middleton M, Byres M, Shoeb M, Nahar L, Sarker SD: Swarnalin and cis-swarnalin, two new tetrahydrofuran derivatives with free radical scavenging activity, from the aerial parts of Cuscuta reflexa. Nat Prod Res. 2007 Jun;21(7):663-8. doi: 10.1080/14786410701371405. [PubMed:17613825 ]
Kayser O, Kolodziej H: Antibacterial activity of extracts and constituents of Pelargonium sidoides and Pelargonium reniforme. Planta Med. 1997 Dec;63(6):508-10. doi: 10.1055/s-2006-957752. [PubMed:9434601 ]

Showing NP-Card for 5,6,7-Trimethoxycoumarin (NP0051461)

MOL for NP0051461 (5,6,7-Trimethoxycoumarin)

3D MOL for NP0051461 (5,6,7-Trimethoxycoumarin)

3D SDF for NP0051461 (5,6,7-Trimethoxycoumarin)

3D-SDF for NP0051461 (5,6,7-Trimethoxycoumarin)

PDB for NP0051461 (5,6,7-Trimethoxycoumarin)

3D PDB for NP0051461 (5,6,7-Trimethoxycoumarin)

SMILES for NP0051461 (5,6,7-Trimethoxycoumarin)

INCHI for NP0051461 (5,6,7-Trimethoxycoumarin)

Structure for NP0051461 (5,6,7-Trimethoxycoumarin)

3D Structure for NP0051461 (5,6,7-Trimethoxycoumarin)