NP-MRD: Showing NP-Card for 7,10,12-Trihydroxycoumestan (NP0056791)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 02:27:04 UTC

Updated at

2022-04-28 02:27:04 UTC

NP-MRD ID

NP0056791

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,10,12-Trihydroxycoumestan

Description

Repensol 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, repensol is considered to be a flavonoid lipid molecule. Repensol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, repensol has been detected, but not quantified in, a few different foods, such as green vegetables, herbs and spices, and tea. 7,10,12-Trihydroxycoumestan is found in Trifolium repens . This could make repensol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -0.1879    1.1769    2.8362 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3939    0.6175    1.8775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6608    0.3005    2.0012 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3084   -0.2959    0.9987 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6387   -0.6154    1.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3070   -1.2316    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6497   -1.5419    0.3189 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -1.5249   -1.0592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3254   -1.2044   -1.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6626   -0.5863   -0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273   -0.2725   -0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5360   -0.4183   -1.3255 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146    0.0567   -0.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9336    0.1302   -1.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0489    0.6909   -1.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2695    0.7646   -1.7910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9243    1.1770    0.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7111    1.1059    0.8667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6061    1.5974    2.1474 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5980    0.5472    0.2879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035    0.3484    0.7210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1428   -0.3754    2.1087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3376   -0.8297    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1877   -2.0127   -1.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7749   -1.4188   -2.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0117   -0.2543   -2.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3734    0.4183   -2.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8028    1.6247    0.6515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3497    2.0260    2.6700 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4 10  2  0
 10  9  1  0
  9  8  2  0
 10 11  1  0
 11 21  2  0
 21 20  1  0
 20 18  2  0
 18 19  1  0
 18 17  1  0
 17 15  2  0
 15 16  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 21  2  1  0
  2  1  2  0
  2  3  1  0
  8  6  1  0
 12 11  1  0
  3  4  1  0
 13 20  1  0
  7 23  1  0
  5 22  1  0
  9 25  1  0
  8 24  1  0
 19 29  1  0
 17 28  1  0
 16 27  1  0
 14 26  1  0
M  END


  Mrv0541 05061307362D          

 21 24  0  0  0  0            999 V2000
    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
   -0.4867    3.2441    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
    0.1682    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
   -0.5259    2.4201    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
    0.2466    3.6222    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
    0.9407    3.1762    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
   -1.2591    2.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    4.4463    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
    1.6731    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
  2  1  2  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  5  2  0  0  0  0
 12  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
 16  6  1  0  0  0  0
 17  7  1  0  0  0  0
 18  9  1  0  0  0  0
 19 15  2  0  0  0  0
 20 11  1  0  0  0  0
 20 14  1  0  0  0  0
 21 10  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056791

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C1=C(C3=C(O)C=C(O)C=C3O1)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C15H8O6/c16-6-1-2-8-10(4-6)21-15(19)13-12-9(18)3-7(17)5-11(12)20-14(8)13/h1-5,16-18H

> <INCHI_KEY>
CFUAZBGEKBTCSH-UHFFFAOYSA-N

> <FORMULA>
C15H8O6

> <MOLECULAR_WEIGHT>
284.2204

> <EXACT_MASS>
284.032087988

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.244056714381358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,12,14-trihydroxy-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>
2.58

> <JCHEM_LOGP>
2.0937560006666662

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.940014865035821

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.071419585310014

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9182363982868913

> <JCHEM_POLAR_SURFACE_AREA>
100.13

> <JCHEM_REFRACTIVITY>
71.6004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,12,14-trihydroxy-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       8.006   3.936   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.756   5.929   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.236   5.399   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.533   8.300   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       3.123   3.846   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.472   7.798   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    8                                                       
CONECT    3    7    9                                                       
CONECT    4    6   10                                                       
CONECT    5    7   11                                                       
CONECT    6    1    4   16                                                  
CONECT    7    3    5   17                                                  
CONECT    8    2   10   14                                                  
CONECT    9    3   12   18                                                  
CONECT   10    4    8   21                                                  
CONECT   11    5   12   20                                                  
CONECT   12    9   11   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14    8   13   20                                                  
CONECT   15   13   19   21                                                  
CONECT   16    6                                                            
CONECT   17    7                                                            
CONECT   18    9                                                            
CONECT   19   15                                                            
CONECT   20   11   14                                                       
CONECT   21   10   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

View in JSmol

Synonyms

Value	Source
3,7,9-Trihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9ci	HMDB
7,10,12-Trihydroxycoumestan	HMDB
Repensol3,7,9-trihydroxycoumestan	HMDB

Chemical Formula

C₁₅H₈O₆

Average Mass

284.2204 Da

Monoisotopic Mass

284.03209 Da

IUPAC Name

5,12,14-trihydroxy-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

5,12,14-trihydroxy-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

Not Available

SMILES

OC1=CC2=C(C=C1)C1=C(C3=C(O)C=C(O)C=C3O1)C(=O)O2

InChI Identifier

InChI=1S/C15H8O6/c16-6-1-2-8-10(4-6)21-15(19)13-12-9(18)3-7(17)5-11(12)20-14(8)13/h1-5,16-18H

InChI Key

CFUAZBGEKBTCSH-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
Trifolium repens	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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Lactone
Polyol
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090029 )

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	2.58	ALOGPS
logP	2.09	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.07	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.6 m³·mol⁻¹	ChemAxon
Polarizability	27.24 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

HMDB0034138

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012413

KNApSAcK ID

C00009758

Chemspider ID

24843113

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257533

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 7,10,12-Trihydroxycoumestan (NP0056791)

MOL for NP0056791 (7,10,12-Trihydroxycoumestan)

3D MOL for NP0056791 (7,10,12-Trihydroxycoumestan)

3D SDF for NP0056791 (7,10,12-Trihydroxycoumestan)

3D-SDF for NP0056791 (7,10,12-Trihydroxycoumestan)

PDB for NP0056791 (7,10,12-Trihydroxycoumestan)

3D PDB for NP0056791 (7,10,12-Trihydroxycoumestan)

SMILES for NP0056791 (7,10,12-Trihydroxycoumestan)

INCHI for NP0056791 (7,10,12-Trihydroxycoumestan)

Structure for NP0056791 (7,10,12-Trihydroxycoumestan)

3D Structure for NP0056791 (7,10,12-Trihydroxycoumestan)