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Showing NP-Card for (3s,4r)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one (NP0235458)

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Record Information
Version2.0
Created at2022-09-06 18:06:02 UTC
Updated at2022-09-06 18:06:02 UTC
NP-MRD IDNP0235458
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3s,4r)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Description(3S,4R)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. (3s,4r)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one is found in Abies nephrolepis. Based on a literature review very few articles have been published on (3S,4R)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0235458 ((3s,4r)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one)


  Mrv1652309062220062D          

 27 29  0  0  1  0            999 V2000
    5.6091   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0284   -2.0811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4131   -0.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715   -0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    0.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015    1.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8547    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678    1.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2524    0.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262   -0.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.1759    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
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 13 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
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
 15 23  1  0  0  0  0
  5 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
Download

3D MOL for NP0235458 ((3s,4r)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one)

Download
3D SDF for NP0235458 ((3s,4r)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one)

  Mrv1652309062220062D          

 27 29  0  0  1  0            999 V2000
    5.6091   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4888   -1.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0284   -2.0811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4131   -0.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715   -0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    0.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1015    1.6988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8547    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678    1.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2524    0.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262   -0.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8946    1.1759    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
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  2  0  0  0  0
 13 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
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 20 23  2  0  0  0  0
 15 23  1  0  0  0  0
  5 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  3 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0235458

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C[C@H]2[C@H](COC2=O)C(=O)C2=CC=C(O)C(OC)=C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O7/c1-25-17-8-11(3-5-15(17)21)7-13-14(10-27-20(13)24)19(23)12-4-6-16(22)18(9-12)26-2/h3-6,8-9,13-14,21-22H,7,10H2,1-2H3/t13-,14-/m0/s1

> <INCHI_KEY>
VBBXDTGECAKSAY-KBPBESRZSA-N

> <FORMULA>
C20H20O7

> <MOLECULAR_WEIGHT>
372.373

> <EXACT_MASS>
372.120902984

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
36.66006163685549

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4R)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

> <JCHEM_LOGP>
2.4813280693333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.953217712075071

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.236414164682053

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5924307750405715

> <JCHEM_POLAR_SURFACE_AREA>
102.29

> <JCHEM_REFRACTIVITY>
96.36980000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4R)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0235458 ((3s,4r)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one)
Download
PDB for NP0235458 ((3s,4r)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      10.470  -0.115   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.137  -0.885   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.803  -0.115   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.469  -0.885   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.512  -2.854   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.572  -4.795   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.032  -4.795   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.091  -2.854   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.053  -3.885   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.771  -1.348   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.693  -0.872   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.014   0.634   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.131   1.665   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.189   3.171   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.595   1.189   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.740   2.219   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.204   1.743   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.916  -0.317   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.803   1.425   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       9.137   2.195   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   26                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   24                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   15                                                       
CONECT   24    5   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    3   27                                                  
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

Download
3D PDB for NP0235458 ((3s,4r)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one)
Download
SMILES for NP0235458 ((3s,4r)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one)
COC1=CC(C[C@H]2[C@H](COC2=O)C(=O)C2=CC=C(O)C(OC)=C2)=CC=C1O
Download
INCHI for NP0235458 ((3s,4r)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one)
InChI=1S/C20H20O7/c1-25-17-8-11(3-5-15(17)21)7-13-14(10-27-20(13)24)19(23)12-4-6-16(22)18(9-12)26-2/h3-6,8-9,13-14,21-22H,7,10H2,1-2H3/t13-,14-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC20H20O7
Average Mass372.3730 Da
Monoisotopic Mass372.12090 Da
IUPAC Name(3S,4R)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
Traditional Name(3S,4R)-4-(4-hydroxy-3-methoxybenzoyl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
CAS Registry NumberNot Available
SMILES
COC1=CC(C[C@H]2[C@H](COC2=O)C(=O)C2=CC=C(O)C(OC)=C2)=CC=C1O
InChI Identifier
InChI=1S/C20H20O7/c1-25-17-8-11(3-5-15(17)21)7-13-14(10-27-20(13)24)19(23)12-4-6-16(22)18(9-12)26-2/h3-6,8-9,13-14,21-22H,7,10H2,1-2H3/t13-,14-/m0/s1
InChI KeyVBBXDTGECAKSAY-KBPBESRZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies nephrolepisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
KingdomOrganic compounds  
Super ClassLignans, neolignans and related compounds  
ClassFuranoid lignans  
Sub ClassTetrahydrofuran lignans  
Direct ParentDibenzylbutyrolactone lignans  
Alternative Parents
Substituents
  • Dibenzylbutyrolactone
    • 

  • Lignan lactone
    • 

  • Alkyl-phenylketone
    • 

  • Methoxyphenol
    • 

  • Phenylketone
    • 

  • Anisole
    • 

  • Benzoyl
    • 

  • Phenoxy compound
    • 

  • Phenol ether
    • 

  • Aryl ketone
    • 

  • Aryl alkyl ketone
    • 

  • Methoxybenzene
    • 

  • Phenol
    • 

  • Alkyl aryl ether
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Gamma butyrolactone
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Carboxylic acid derivative
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP2.48ChemAxon
pKa (Strongest Acidic)8.24ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.29 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity96.37 m³·mol⁻¹ChemAxon
Polarizability36.66 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162892832  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]