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Showing NP-Card for Wairol (NP0047811)

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Record Information
Version2.0
Created at2022-03-17 20:46:22 UTC
Updated at2022-03-17 20:46:22 UTC
NP-MRD IDNP0047811
Secondary Accession NumbersNone
Natural Product Identification
Common NameWairol
DescriptionWairol 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, wairol is considered to be a flavonoid lipid molecule. Wairol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Wairol has been detected, but not quantified in, alfalfa and pulses. Wairol is found in Ascochyta imperfecta. This could make wairol a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047811 (Wairol)


  Mrv0541 05061307292D          

 23 26  0  0  0  0            999 V2000
   -1.9532    2.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0191    4.8244    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
   -0.4867    3.2441    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
    3.3838    3.4879    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
    0.9014    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
    1.6548    4.8202    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
    1.6731    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  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  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  9  1  0  0  0  0
 21  2  1  0  0  0  0
 21 12  1  0  0  0  0
 22 13  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
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3D MOL for NP0047811 (Wairol)

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3D SDF for NP0047811 (Wairol)

  Mrv0541 05061307292D          

 23 26  0  0  0  0            999 V2000
   -1.9532    2.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0191    4.8244    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
   -0.4867    3.2441    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
    3.3838    3.4879    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
    0.9014    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
    1.6548    4.8202    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
    1.6731    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  6  2  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  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  9  1  0  0  0  0
 21  2  1  0  0  0  0
 21 12  1  0  0  0  0
 22 13  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>
NP0047811

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
GYNHMEBOILXPQT-UHFFFAOYSA-N

> <FORMULA>
C17H12O6

> <MOLECULAR_WEIGHT>
312.2736

> <EXACT_MASS>
312.063388116

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.346714831997502

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-12,14-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>
2.48

> <JCHEM_LOGP>
2.385544112666666

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.1565543727419385

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8612841439459626

> <JCHEM_POLAR_SURFACE_AREA>
78.13000000000001

> <JCHEM_REFRACTIVITY>
80.56500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
wairol

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047811 (Wairol)
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PDB for NP0047811 (Wairol)
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      -3.646   4.644   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.902   9.006   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      -0.909   6.056   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      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.624   5.135   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       0.460   6.761   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.756   5.929   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      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.533   8.300   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   10                                                       
CONECT    5    8   11                                                       
CONECT    6    9   12                                                       
CONECT    7    9   13                                                       
CONECT    8    3    5   18                                                  
CONECT    9    6    7   20                                                  
CONECT   10    4   11   16                                                  
CONECT   11    5   10   23                                                  
CONECT   12    6   14   21                                                  
CONECT   13    7   14   22                                                  
CONECT   14   12   13   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   10   15   22                                                  
CONECT   17   15   19   23                                                  
CONECT   18    8                                                            
CONECT   19   17                                                            
CONECT   20    1    9                                                       
CONECT   21    2   12                                                       
CONECT   22   13   16                                                       
CONECT   23   11   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

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3D PDB for NP0047811 (Wairol)
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SMILES for NP0047811 (Wairol)
COC1=CC(OC)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1
Download
INCHI for NP0047811 (Wairol)
InChI=1S/C17H12O6/c1-20-9-6-12(21-2)14-13(7-9)22-16-10-4-3-8(18)5-11(10)23-17(19)15(14)16/h3-7,18H,1-2H3
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Synonyms
ValueSource
3-Hydroxy-7,9-dimethoxycoumestanHMDB
7-Hydroxy-10,12-dimethoxycoumestanHMDB
Chemical FormulaC17H12O6
Average Mass312.2736 Da
Monoisotopic Mass312.06339 Da
IUPAC Name5-hydroxy-12,14-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 Namewairol
CAS Registry Number77331-73-8
SMILES
COC1=CC(OC)=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1
InChI Identifier
InChI=1S/C17H12O6/c1-20-9-6-12(21-2)14-13(7-9)22-16-10-4-3-8(18)5-11(10)23-17(19)15(14)16/h3-7,18H,1-2H3
InChI KeyGYNHMEBOILXPQT-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ascochyta imperfectaFungi
Medicago sativaFooDB
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.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassIsoflavonoids  
Sub ClassCoumestans  
Direct ParentCoumestans  
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.48ALOGPS
logP2.39ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.16ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area78.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity80.56 m³·mol⁻¹ChemAxon
Polarizability31.35 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033993  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012227  
KNApSAcK IDC00009767  
Chemspider ID4589918  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5488650  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available