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Showing NP-Card for 2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-5,7-diol (NP0214588)

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Record Information
Version2.0
Created at2022-09-05 13:55:57 UTC
Updated at2022-09-05 13:55:57 UTC
NP-MRD IDNP0214588
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-5,7-diol
Description2-(3-Hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-5,7-diol belongs to the class of organic compounds known as 8-prenylated flavans. These are flavans that features a C5-isoprenoid substituent at the 8-position. 2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-5,7-diol is found in Cyperus conglomeratus. 2-(3-Hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-5,7-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0214588 (2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-5,7-diol)


  Mrv0541 04121512092D          

 26 28  0  0  0  0            999 V2000
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
   -1.4289   -1.6500    0.0000 C   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 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
    0.0000   -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
    0.7145   -0.4125    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   -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 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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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 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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 19 25  2  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 26  1  0  0  0  0
M  END
Download

3D MOL for NP0214588 (2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-5,7-diol)

Download
3D SDF for NP0214588 (2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-5,7-diol)

  Mrv0541 04121512092D          

 26 28  0  0  0  0            999 V2000
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    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
   -1.4289   -1.6500    0.0000 C   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 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
    0.0000   -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
    0.7145   -0.4125    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   -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 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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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 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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 19 25  2  0  0  0  0
 13 25  1  0  0  0  0
 25 26  1  0  0  0  0
 10 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0214588

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=CC(=C1)C1CCC2=C(O)C=C(O)C(CC=C(C)C)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O5/c1-12(2)4-5-16-18(23)11-19(24)17-6-7-20(26-21(16)17)13-8-14(22)10-15(9-13)25-3/h4,8-11,20,22-24H,5-7H2,1-3H3

> <INCHI_KEY>
HGORYRLTYUTUHO-UHFFFAOYSA-N

> <FORMULA>
C21H24O5

> <MOLECULAR_WEIGHT>
356.418

> <EXACT_MASS>
356.162373873

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.58800280322268

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-5,7-diol

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
4.744471677666666

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.677558659378308

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.078313713973795

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5718406260064315

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
101.3633

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-5,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0214588 (2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-5,7-diol)
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PDB for NP0214588 (2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-5,7-diol)
HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -0.770   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  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   25                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   19   13   26                                                  
CONECT   26   25   10                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

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3D PDB for NP0214588 (2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-5,7-diol)
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SMILES for NP0214588 (2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-5,7-diol)
COC1=CC(O)=CC(=C1)C1CCC2=C(O)C=C(O)C(CC=C(C)C)=C2O1
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INCHI for NP0214588 (2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-5,7-diol)
InChI=1S/C21H24O5/c1-12(2)4-5-16-18(23)11-19(24)17-6-7-20(26-21(16)17)13-8-14(22)10-15(9-13)25-3/h4,8-11,20,22-24H,5-7H2,1-3H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC21H24O5
Average Mass356.4180 Da
Monoisotopic Mass356.16237 Da
IUPAC Name2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-5,7-diol
Traditional Name2-(3-hydroxy-5-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-5,7-diol
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=CC(=C1)C1CCC2=C(O)C=C(O)C(CC=C(C)C)=C2O1
InChI Identifier
InChI=1S/C21H24O5/c1-12(2)4-5-16-18(23)11-19(24)17-6-7-20(26-21(16)17)13-8-14(22)10-15(9-13)25-3/h4,8-11,20,22-24H,5-7H2,1-3H3
InChI KeyHGORYRLTYUTUHO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cyperus conglomeratusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 8-prenylated flavans. These are flavans that features a C5-isoprenoid substituent at the 8-position.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassFlavonoids  
Sub ClassFlavans  
Direct Parent8-prenylated flavans  
Alternative Parents
Substituents
  • 8-prenylated flavan
    • 

  • 3p-methoxyflavonoid-skeleton
    • 

  • 7-hydroxyflavonoid
    • 

  • 3'-hydroxyflavonoid
    • 

  • Hydroxyflavonoid
    • 

  • 5-hydroxyflavonoid
    • 

  • Chromane
    • 

  • Benzopyran
    • 

  • Methoxyphenol
    • 

  • 1-benzopyran
    • 

  • Anisole
    • 

  • Phenoxy compound
    • 

  • Methoxybenzene
    • 

  • Phenol ether
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Organoheterocyclic compound
    • 

  • Organic oxygen compound
    • 

  • 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
logP3.64ALOGPS
logP4.74ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.08ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.15 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity101.36 m³·mol⁻¹ChemAxon
Polarizability38.59 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 Compound91127489  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]