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Showing NP-Card for 6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-1,4-dihydro-2-benzopyran-3-one (NP0196867)

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Record Information
Version2.0
Created at2022-09-04 15:01:20 UTC
Updated at2022-09-04 15:01:20 UTC
NP-MRD IDNP0196867
Secondary Accession NumbersNone
Natural Product Identification
Common Name6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-1,4-dihydro-2-benzopyran-3-one
Description6,7,8-Trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-3,4-dihydro-1H-2-benzopyran-3-one belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. 6,7,8-Trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-3,4-dihydro-1H-2-benzopyran-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0196867 (6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-1,4-dihydro-2-benzopyran-3-one)


  Mrv1533004251504142D          

 20 21  0  0  0  0            999 V2000
    1.4289   -2.4750    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
    0.7145   -1.2375    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
    0.0000    0.0000    0.0000 O   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 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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    2.8579    2.4750    0.0000 C   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
    4.2868   -1.6500    0.0000 O   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
    2.8579   -2.4750    0.0000 O   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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  2 20  1  0  0  0  0
  7 20  1  0  0  0  0
M  END
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3D MOL for NP0196867 (6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-1,4-dihydro-2-benzopyran-3-one)

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3D SDF for NP0196867 (6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-1,4-dihydro-2-benzopyran-3-one)

  Mrv1533004251504142D          

 20 21  0  0  0  0            999 V2000
    1.4289   -2.4750    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
    0.7145   -1.2375    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
    0.0000    0.0000    0.0000 O   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 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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    2.8579    2.4750    0.0000 C   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
    4.2868   -1.6500    0.0000 O   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
    2.8579   -2.4750    0.0000 O   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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
  2 20  1  0  0  0  0
  7 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196867

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(=O)CC2=C(CC=C(C)C)C(O)=C(O)C(O)=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O5/c1-7(2)4-5-9-10-6-11(16)20-8(3)12(10)14(18)15(19)13(9)17/h4,8,17-19H,5-6H2,1-3H3

> <INCHI_KEY>
BADOYDRZVCGQJD-UHFFFAOYSA-N

> <FORMULA>
C15H18O5

> <MOLECULAR_WEIGHT>
278.304

> <EXACT_MASS>
278.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
28.62978227674919

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-3,4-dihydro-1H-2-benzopyran-3-one

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
2.7425615216666666

> <ALOGPS_LOGS>
-2.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.74117586338213

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.582117557300197

> <JCHEM_PKA_STRONGEST_BASIC>
-6.059499727115619

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
75.2936

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-1,4-dihydro-2-benzopyran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0196867 (6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-1,4-dihydro-2-benzopyran-3-one)
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PDB for NP0196867 (6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-1,4-dihydro-2-benzopyran-3-one)
HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   0.000   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18    2    7                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

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3D PDB for NP0196867 (6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-1,4-dihydro-2-benzopyran-3-one)
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SMILES for NP0196867 (6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-1,4-dihydro-2-benzopyran-3-one)
CC1OC(=O)CC2=C(CC=C(C)C)C(O)=C(O)C(O)=C12
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INCHI for NP0196867 (6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-1,4-dihydro-2-benzopyran-3-one)
InChI=1S/C15H18O5/c1-7(2)4-5-9-10-6-11(16)20-8(3)12(10)14(18)15(19)13(9)17/h4,8,17-19H,5-6H2,1-3H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H18O5
Average Mass278.3040 Da
Monoisotopic Mass278.11542 Da
IUPAC Name6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-3,4-dihydro-1H-2-benzopyran-3-one
Traditional Name6,7,8-trihydroxy-1-methyl-5-(3-methylbut-2-en-1-yl)-1,4-dihydro-2-benzopyran-3-one
CAS Registry NumberNot Available
SMILES
CC1OC(=O)CC2=C(CC=C(C)C)C(O)=C(O)C(O)=C12
InChI Identifier
InChI=1S/C15H18O5/c1-7(2)4-5-9-10-6-11(16)20-8(3)12(10)14(18)15(19)13(9)17/h4,8,17-19H,5-6H2,1-3H3
InChI KeyBADOYDRZVCGQJD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassBenzopyrans  
Sub Class2-benzopyrans  
Direct Parent2-benzopyrans  
Alternative Parents
Substituents
  • 2-benzopyran
    • 

  • Benzenoid
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Polyol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP2.56ALOGPS
logP2.74ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)8.58ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity75.29 m³·mol⁻¹ChemAxon
Polarizability28.63 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]