NP-MRD: Showing NP-Card for 3-Hydroxy-8,9-dimethoxycoumestan (NP0045943)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 19:45:47 UTC

Updated at

2022-03-17 19:45:47 UTC

NP-MRD ID

NP0045943

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Hydroxy-8,9-dimethoxycoumestan

Description

3-Hydroxy-8,9-dimethoxycoumestan, also known as alpha-ethyl-3-nitrocinnamic acid, belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, 3-hydroxy-8,9-dimethoxycoumestan is considered to be a flavonoid lipid molecule. 3-Hydroxy-8,9-dimethoxycoumestan is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3-hydroxy-8,9-dimethoxycoumestan has been detected, but not quantified in, alfalfa and pulses. 3-Hydroxy-8,9-dimethoxycoumestan is found in Melilotus messanensis and Myroxylon balsamum . This could make 3-hydroxy-8,9-dimethoxycoumestan a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305212D          

 23 26  0  0  0  0            999 V2000
   -1.9140    3.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9532    2.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2891    2.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    2.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2075    3.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466    3.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    2.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0128    2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9407    3.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    3.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    2.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    3.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    2.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365    3.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    4.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4838    2.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548    4.8202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1807    3.6901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2591    2.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312    4.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  4  1  0  0  0  0
 10  6  2  0  0  0  0
 11  5  1  0  0  0  0
 11  9  2  0  0  0  0
 12  7  2  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14 13  2  0  0  0  0
 15 10  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  2  0  0  0  0
 17 15  1  0  0  0  0
 18  8  1  0  0  0  0
 19 17  2  0  0  0  0
 20  1  1  0  0  0  0
 20 13  1  0  0  0  0
 21  2  1  0  0  0  0
 21 14  1  0  0  0  0
 22 12  1  0  0  0  0
 22 16  1  0  0  0  0
 23 11  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045943

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O6/c1-20-13-6-10-12(7-14(13)21-2)22-16-9-4-3-8(18)5-11(9)23-17(19)15(10)16/h3-7,18H,1-2H3

> <INCHI_KEY>
PKLPURDVDNBFCI-UHFFFAOYSA-N

> <FORMULA>
C17H12O6

> <MOLECULAR_WEIGHT>
312.2736

> <EXACT_MASS>
312.063388116

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.595376212289068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-13,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.385544112666666

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.117751669730867

> <JCHEM_PKA_STRONGEST_BASIC>
-4.109703129647038

> <JCHEM_POLAR_SURFACE_AREA>
78.13000000000001

> <JCHEM_REFRACTIVITY>
80.56500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-13,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

> <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      -3.573   6.182   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.646   4.644   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.006   3.936   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.756   5.929   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.236   5.399   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.089   8.998   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.204   6.888   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.123   3.846   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.472   7.798   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    8   11                                                       
CONECT    6   10   13                                                       
CONECT    7   12   14                                                       
CONECT    8    3    5   18                                                  
CONECT    9    4   11   16                                                  
CONECT   10    6   12   15                                                  
CONECT   11    5    9   23                                                  
CONECT   12    7   10   22                                                  
CONECT   13    6   14   20                                                  
CONECT   14    7   13   21                                                  
CONECT   15   10   16   17                                                  
CONECT   16    9   15   22                                                  
CONECT   17   15   19   23                                                  
CONECT   18    8                                                            
CONECT   19   17                                                            
CONECT   20    1   13                                                       
CONECT   21    2   14                                                       
CONECT   22   12   16                                                       
CONECT   23   11   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

View in JSmol

Synonyms

Value	Source
7-Hydroxy-11,12-dimethoxycoumestan (obsol.)	HMDB
alpha-Ethyl-3-nitrocinnamic acid	HMDB

Chemical Formula

C₁₇H₁₂O₆

Average Mass

312.2736 Da

Monoisotopic Mass

312.06339 Da

IUPAC Name

5-hydroxy-13,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

Traditional Name

5-hydroxy-13,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

CAS Registry Number

5252-40-4

SMILES

COC1=C(OC)C=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1

InChI Identifier

InChI=1S/C17H12O6/c1-20-13-6-10-12(7-14(13)21-2)22-16-9-4-3-8(18)5-11(9)23-17(19)15(10)16/h3-7,18H,1-2H3

InChI Key

PKLPURDVDNBFCI-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
Medicago sativa	FooDB	KNAPSACK
Melilotus messanensis	Plant	KNApSAcK
Myroxylon balsamum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Benzofuran
Furopyran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090028 )

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	2.5	ALOGPS
logP	2.39	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	78.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.56 m³·mol⁻¹	ChemAxon
Polarizability	31.6 Å³	ChemAxon
Number of Rings	4	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

HMDB0030561

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002445

KNApSAcK ID

C00009768

Chemspider ID

4678016

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5748556

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3-Hydroxy-8,9-dimethoxycoumestan (NP0045943)

MOL for NP0045943 (3-Hydroxy-8,9-dimethoxycoumestan)

3D MOL for NP0045943 (3-Hydroxy-8,9-dimethoxycoumestan)

3D SDF for NP0045943 (3-Hydroxy-8,9-dimethoxycoumestan)

3D-SDF for NP0045943 (3-Hydroxy-8,9-dimethoxycoumestan)

PDB for NP0045943 (3-Hydroxy-8,9-dimethoxycoumestan)

3D PDB for NP0045943 (3-Hydroxy-8,9-dimethoxycoumestan)

SMILES for NP0045943 (3-Hydroxy-8,9-dimethoxycoumestan)

INCHI for NP0045943 (3-Hydroxy-8,9-dimethoxycoumestan)

Structure for NP0045943 (3-Hydroxy-8,9-dimethoxycoumestan)

3D Structure for NP0045943 (3-Hydroxy-8,9-dimethoxycoumestan)