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Showing NP-Card for 5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-2,3-dihydro-1-benzopyran-4-one (NP0327162)

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Record Information
Version2.0
Created at2022-09-12 09:27:58 UTC
Updated at2022-09-12 09:27:58 UTC
NP-MRD IDNP0327162
Secondary Accession NumbersNone
Natural Product Identification
Common Name5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-2,3-dihydro-1-benzopyran-4-one
DescriptionMuscomin belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position. Muscomin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Muscomin has been detected, but not quantified in, herbs and spices. 5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-2,3-dihydro-1-benzopyran-4-one is found in Leopoldia comosa, Muscari neglectum and Veltheimia bracteata. This could make muscomin a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0327162 (5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-2,3-dihydro-1-benzopyran-4-one)


  Mrv0541 05061309402D          

 25 27  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -1.4289    0.8250    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   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
    0.7145   -0.4125    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    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 16 12  2  0  0  0  0
 16 15  1  0  0  0  0
 17 14  2  0  0  0  0
 18 15  2  0  0  0  0
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 20 13  2  0  0  0  0
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 23 17  1  0  0  0  0
 24  2  1  0  0  0  0
 24 18  1  0  0  0  0
 25  8  1  0  0  0  0
 25 16  1  0  0  0  0
M  END
Download

3D MOL for NP0327162 (5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-2,3-dihydro-1-benzopyran-4-one)

Download
3D SDF for NP0327162 (5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-2,3-dihydro-1-benzopyran-4-one)

  Mrv0541 05061309402D          

 25 27  0  0  0  0            999 V2000
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    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
   -1.4289    0.8250    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   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
    0.7145   -0.4125    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    0.8250    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  7  1  0  0  0  0
 10  8  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  1  0  0  0  0
 16 12  2  0  0  0  0
 16 15  1  0  0  0  0
 17 14  2  0  0  0  0
 18 15  2  0  0  0  0
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 20 13  2  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23  1  1  0  0  0  0
 23 17  1  0  0  0  0
 24  2  1  0  0  0  0
 24 18  1  0  0  0  0
 25  8  1  0  0  0  0
 25 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327162

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C2=C(C(=O)C(CC3=CC=C(O)C=C3)CO2)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O7/c1-23-17-14(21)12-13(20)10(7-9-3-5-11(19)6-4-9)8-25-16(12)15(22)18(17)24-2/h3-6,10,19,21-22H,7-8H2,1-2H3

> <INCHI_KEY>
PGCPWPPPMWXCMG-UHFFFAOYSA-N

> <FORMULA>
C18H18O7

> <MOLECULAR_WEIGHT>
346.3313

> <EXACT_MASS>
346.10525293

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
34.314716583156674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.51

> <JCHEM_LOGP>
2.8568842476666663

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.75436501828717

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.14640628102314

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9764633616161014

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
89.20389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0327162 (5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-2,3-dihydro-1-benzopyran-4-one)
Download
PDB for NP0327162 (5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-2,3-dihydro-1-benzopyran-4-one)
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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   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  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   23                                                            
CONECT    2   24                                                            
CONECT    3    5    9                                                       
CONECT    4    6    9                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    9   10                                                       
CONECT    8   10   25                                                       
CONECT    9    3    4    7                                                  
CONECT   10    7    8   13                                                  
CONECT   11    5    6   19                                                  
CONECT   12   13   14   16                                                  
CONECT   13   10   12   20                                                  
CONECT   14   12   17   21                                                  
CONECT   15   16   18   22                                                  
CONECT   16   12   15   25                                                  
CONECT   17   14   18   23                                                  
CONECT   18   15   17   24                                                  
CONECT   19   11                                                            
CONECT   20   13                                                            
CONECT   21   14                                                            
CONECT   22   15                                                            
CONECT   23    1   17                                                       
CONECT   24    2   18                                                       
CONECT   25    8   16                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

Download
3D PDB for NP0327162 (5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-2,3-dihydro-1-benzopyran-4-one)
Download
SMILES for NP0327162 (5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-2,3-dihydro-1-benzopyran-4-one)
COC1=C(O)C2=C(C(=O)C(CC3=CC=C(O)C=C3)CO2)C(O)=C1OC
Download
INCHI for NP0327162 (5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-2,3-dihydro-1-benzopyran-4-one)
InChI=1S/C18H18O7/c1-23-17-14(21)12-13(20)10(7-9-3-5-11(19)6-4-9)8-25-16(12)15(22)18(17)24-2/h3-6,10,19,21-22H,7-8H2,1-2H3
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Synonyms
ValueSource
MuscominMeSH
Chemical FormulaC18H18O7
Average Mass346.3313 Da
Monoisotopic Mass346.10525 Da
IUPAC Name5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-6,7-dimethoxy-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
COC1=C(O)C2=C(C(=O)C(CC3=CC=C(O)C=C3)CO2)C(O)=C1OC
InChI Identifier
InChI=1S/C18H18O7/c1-23-17-14(21)12-13(20)10(7-9-3-5-11(19)6-4-9)8-25-16(12)15(22)18(17)24-2/h3-6,10,19,21-22H,7-8H2,1-2H3
InChI KeyPGCPWPPPMWXCMG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Muscari comosumLOTUS Database
Muscari neglectumLOTUS Database
Veltheimia bracteataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassHomoisoflavonoids  
Sub ClassHomoisoflavans  
Direct ParentHomoisoflavanones  
Alternative Parents
Substituents
  • Homoisoflavanone
    • 

  • Chromone
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • Anisole
    • 

  • Aryl ketone
    • 

  • Aryl alkyl ketone
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Vinylogous acid
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP2.51ALOGPS
logP2.86ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.15ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area105.45 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity89.2 m³·mol⁻¹ChemAxon
Polarizability34.31 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037250  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB016261  
KNApSAcK IDNot Available
Chemspider ID10254757  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14427389  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]