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Showing NP-Card for (2s,3r)-4-(2h-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one (NP0305350)

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Record Information
Version2.0
Created at2022-09-10 21:06:55 UTC
Updated at2022-09-10 21:06:55 UTC
NP-MRD IDNP0305350
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s,3r)-4-(2h-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one
DescriptionOleiferin D belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety. (2s,3r)-4-(2h-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one is found in Bicuiba oleifera and Iryanthera lancifolia. Based on a literature review very few articles have been published on oleiferin D.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0305350 ((2s,3r)-4-(2h-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one)


  Mrv1652309102223062D          

 25 27  0  0  1  0            999 V2000
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 O   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
   -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
   -0.7145   -2.0625    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
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  2  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
    1.4289   -2.4750    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
    2.1434   -1.2375    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
    3.5724   -2.0625    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
    4.3570   -2.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    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
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 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
 16 21  1  0  0  0  0
  5 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
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3D MOL for NP0305350 ((2s,3r)-4-(2h-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one)

Download
3D SDF for NP0305350 ((2s,3r)-4-(2h-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one)

  Mrv1652309102223062D          

 25 27  0  0  1  0            999 V2000
   -4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 O   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
   -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
   -0.7145   -2.0625    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
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  2  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
    1.4289   -2.4750    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
    2.1434   -1.2375    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
    3.5724   -2.0625    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
    4.3570   -2.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    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
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 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
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 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
 16 21  1  0  0  0  0
  5 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0305350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C(=O)[C@@H](C)[C@H](C)CC1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O5/c1-12(8-14-4-7-17-19(9-14)25-11-24-17)13(2)20(22)15-5-6-16(21)18(10-15)23-3/h4-7,9-10,12-13,21H,8,11H2,1-3H3/t12-,13+/m1/s1

> <INCHI_KEY>
UFCKYLUYWNYRRX-OLZOCXBDSA-N

> <FORMULA>
C20H22O5

> <MOLECULAR_WEIGHT>
342.391

> <EXACT_MASS>
342.146723808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
36.66999010148358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-4-(2H-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one

> <JCHEM_LOGP>
4.246372739333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.338528362611903

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.255167615398983

> <JCHEM_PKA_STRONGEST_BASIC>
-4.511417490951915

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
93.71880000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-4-(2H-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0305350 ((2s,3r)-4-(2h-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one)
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PDB for NP0305350 ((2s,3r)-4-(2h-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one)
HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.668  -3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -3.850   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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.133  -4.326   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.038  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.133  -1.834   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22    5   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    3   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

Download
3D PDB for NP0305350 ((2s,3r)-4-(2h-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one)
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SMILES for NP0305350 ((2s,3r)-4-(2h-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one)
COC1=CC(=CC=C1O)C(=O)[C@@H](C)[C@H](C)CC1=CC=C2OCOC2=C1
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INCHI for NP0305350 ((2s,3r)-4-(2h-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one)
InChI=1S/C20H22O5/c1-12(8-14-4-7-17-19(9-14)25-11-24-17)13(2)20(22)15-5-6-16(21)18(10-15)23-3/h4-7,9-10,12-13,21H,8,11H2,1-3H3/t12-,13+/m1/s1
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SynonymsNot Available
Chemical FormulaC20H22O5
Average Mass342.3910 Da
Monoisotopic Mass342.14672 Da
IUPAC Name(2S,3R)-4-(2H-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one
Traditional Name(2S,3R)-4-(2H-1,3-benzodioxol-5-yl)-1-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbutan-1-one
CAS Registry NumberNot Available
SMILES
COC1=CC(=CC=C1O)C(=O)[C@@H](C)[C@H](C)CC1=CC=C2OCOC2=C1
InChI Identifier
InChI=1S/C20H22O5/c1-12(8-14-4-7-17-19(9-14)25-11-24-17)13(2)20(22)15-5-6-16(21)18(10-15)23-3/h4-7,9-10,12-13,21H,8,11H2,1-3H3/t12-,13+/m1/s1
InChI KeyUFCKYLUYWNYRRX-OLZOCXBDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Bicuiba oleiferaLOTUS Database
Iryanthera lancifoliaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzylbutane lignans. These are lignan compounds containing a 2,3-dibenzylbutane moiety.
KingdomOrganic compounds  
Super ClassLignans, neolignans and related compounds  
ClassDibenzylbutane lignans  
Sub ClassNot Available
Direct ParentDibenzylbutane lignans  
Alternative Parents
Substituents
  • Dibenzylbutane lignan skeleton
    • 

  • Alkyl-phenylketone
    • 

  • Butyrophenone
    • 

  • Methoxyphenol
    • 

  • Benzodioxole
    • 

  • Phenylketone
    • 

  • Phenylpropane
    • 

  • Phenoxy compound
    • 

  • Anisole
    • 

  • Benzoyl
    • 

  • Methoxybenzene
    • 

  • Aryl alkyl ketone
    • 

  • Aryl ketone
    • 

  • Phenol ether
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Ketone
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Aldehyde
    • 

  • Organooxygen 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
logP4.25ChemAxon
pKa (Strongest Acidic)8.26ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity93.72 m³·mol⁻¹ChemAxon
Polarizability36.67 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID23317925  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44450596  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]