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Showing NP-Card for (2s)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one (NP0327310)

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Record Information
Version2.0
Created at2022-09-12 09:46:51 UTC
Updated at2022-09-12 09:46:51 UTC
NP-MRD IDNP0327310
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one
Description(2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position. (2s)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one is found in Flourensia fiebrigii. Based on a literature review very few articles have been published on (2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0327310 ((2s)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)


  Mrv1652309122211462D          

 25 27  0  0  1  0            999 V2000
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    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
   -1.4289   -0.0000    0.0000 O   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   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   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
    2.1434   -1.2375    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
    1.4289   -2.4750    0.0000 O   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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
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 15 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
Download

3D MOL for NP0327310 ((2s)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)

Download
3D SDF for NP0327310 ((2s)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)

  Mrv1652309122211462D          

 25 27  0  0  1  0            999 V2000
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    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
   -1.4289   -0.0000    0.0000 O   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   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   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
    2.1434   -1.2375    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
    1.4289   -2.4750    0.0000 O   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
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 11 24  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0327310

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C=CC2=C1O[C@@H](CC2=O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O5/c1-11(2)3-5-13-15(21)8-6-14-17(23)10-19(25-20(13)14)12-4-7-16(22)18(24)9-12/h3-4,6-9,19,21-22,24H,5,10H2,1-2H3/t19-/m0/s1

> <INCHI_KEY>
ADFZZQAJJGHYDR-IBGZPJMESA-N

> <FORMULA>
C20H20O5

> <MOLECULAR_WEIGHT>
340.375

> <EXACT_MASS>
340.131073744

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
35.76486172527872

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

> <JCHEM_LOGP>
3.913675049666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.223061630446045

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.598094449939797

> <JCHEM_PKA_STRONGEST_BASIC>
-4.950431384354126

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
95.5326

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0327310 ((2s)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)
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PDB for NP0327310 ((2s)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   24                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15                                                       
CONECT   23   14   24                                                       
CONECT   24   23   11   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

Download
3D PDB for NP0327310 ((2s)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)
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SMILES for NP0327310 ((2s)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)
CC(C)=CCC1=C(O)C=CC2=C1O[C@@H](CC2=O)C1=CC=C(O)C(O)=C1
Download
INCHI for NP0327310 ((2s)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one)
InChI=1S/C20H20O5/c1-11(2)3-5-13-15(21)8-6-14-17(23)10-19(25-20(13)14)12-4-7-16(22)18(24)9-12/h3-4,6-9,19,21-22,24H,5,10H2,1-2H3/t19-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H20O5
Average Mass340.3750 Da
Monoisotopic Mass340.13107 Da
IUPAC Name(2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name(2S)-2-(3,4-dihydroxyphenyl)-7-hydroxy-8-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
CC(C)=CCC1=C(O)C=CC2=C1O[C@@H](CC2=O)C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C20H20O5/c1-11(2)3-5-13-15(21)8-6-14-17(23)10-19(25-20(13)14)12-4-7-16(22)18(24)9-12/h3-4,6-9,19,21-22,24H,5,10H2,1-2H3/t19-/m0/s1
InChI KeyADFZZQAJJGHYDR-IBGZPJMESA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Flourensia fiebrigiiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 8-position.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavans  
Direct Parent8-prenylated flavanones  
Alternative Parents
Substituents
  • 8-prenylated flavanone
    • 

  • Flavanone
    • 

  • Hydroxyflavonoid
    • 

  • 3'-hydroxyflavonoid
    • 

  • 4'-hydroxyflavonoid
    • 

  • 7-hydroxyflavonoid
    • 

  • Chromone
    • 

  • Benzopyran
    • 

  • Chromane
    • 

  • 1-benzopyran
    • 

  • Catechol
    • 

  • Aryl alkyl ketone
    • 

  • Aryl ketone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Alkyl aryl ether
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP3.91ChemAxon
pKa (Strongest Acidic)7.6ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.53 m³·mol⁻¹ChemAxon
Polarizability35.76 ųChemAxon
Number of Rings3ChemAxon
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 Compound25837768  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]