NP-MRD: Showing NP-Card for 6'-Hydroxyenterolactone (NP0339405)

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Record Information

Version

2.0

Created at

2024-09-11 21:40:47 UTC

Updated at

2024-09-11 21:40:48 UTC

NP-MRD ID

NP0339405

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6'-Hydroxyenterolactone

Description

6'-Hydroxyenterolactone belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Based on a literature review very few articles have been published on 6'-Hydroxyenterolactone.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05272300132D          

 23 25  0  0  0  0            999 V2000
   -0.1499    2.0795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8174    1.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5624    0.8099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2626    0.8099    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5175    1.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6020    1.8495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0474    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    0.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7240    1.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9035    0.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5680    0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0529   -0.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8734   -0.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2089    0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0239    1.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5088    0.4012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1732   -0.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3528   -0.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8678    0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2034    0.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6582   -1.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3583   -1.0199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4186    1.6498    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  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  1  0  0  0
  4  8  1  6  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
  8 11  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 15 20  2  0  0  0  0
  7 19  1  0  0  0  0
 17 21  1  0  0  0  0
 13 22  1  0  0  0  0
 10 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339405

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC(C[C@@H]2[C@@H](CC3=CC(O)=CC=C3O)COC2=O)=C1

> <INCHI_IDENTIFIER>
InChI=1/C18H18O5/c19-14-3-1-2-11(6-14)7-16-13(10-23-18(16)22)8-12-9-15(20)4-5-17(12)21/h1-6,9,13,16,19-21H,7-8,10H2/t13-,16+/s2

> <INCHI_KEY>
OUWRXHXCIKQNEC-WKTCHCBJNA-N

> <FORMULA>
C18H18O5

> <MOLECULAR_WEIGHT>
314.337

> <EXACT_MASS>
314.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.706385377238394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R)-4-[(2,5-dihydroxyphenyl)methyl]-3-[(3-hydroxyphenyl)methyl]oxolan-2-one

> <JCHEM_LOGP>
3.303559720666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.809120825103808

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.206622907665636

> <JCHEM_PKA_STRONGEST_BASIC>
-5.894065228718977

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
84.6889

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R)-4-[(2,5-dihydroxyphenyl)methyl]-3-[(3-hydroxyphenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  O   UNK     0      -0.280   3.882   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.526   2.977   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.050   1.512   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.490   1.512   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.966   2.977   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.990   3.452   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.955   0.266   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.395   0.266   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.085   1.995   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.553   1.834   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.927   0.427   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.832  -0.819   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.364  -0.658   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.990   0.749   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.645   1.995   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.550   0.749   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.923  -0.658   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.392  -0.819   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.487   0.427   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.113   1.834   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.829  -1.904   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.269  -1.904   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.648   3.080   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    1                                                       
CONECT    6    2                                                            
CONECT    7    3   19                                                       
CONECT    8    4   11                                                       
CONECT    9   10   14                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12    8                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13    9                                                       
CONECT   15   16   20                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   21                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20    7                                                  
CONECT   20   19   15                                                       
CONECT   21   17                                                            
CONECT   22   13                                                            
CONECT   23   10                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₈O₅

Average Mass

314.3370 Da

Monoisotopic Mass

314.11542 Da

IUPAC Name

(3R,4R)-4-[(2,5-dihydroxyphenyl)methyl]-3-[(3-hydroxyphenyl)methyl]oxolan-2-one

Traditional Name

(3R,4R)-4-[(2,5-dihydroxyphenyl)methyl]-3-[(3-hydroxyphenyl)methyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

OC1=CC=CC(C[C@@H]2[C@@H](CC3=CC(O)=CC=C3O)COC2=O)=C1

InChI Identifier

InChI=1/C18H18O5/c19-14-3-1-2-11(6-14)7-16-13(10-23-18(16)22)8-12-9-15(20)4-5-17(12)21/h1-6,9,13,16,19-21H,7-8,10H2/t13-,16+/s2

InChI Key

OUWRXHXCIKQNEC-WKTCHCBJNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
Hydroquinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Gamma butyrolactone
Benzenoid
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.3	ChemAxon
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-5.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.69 m³·mol⁻¹	ChemAxon
Polarizability	31.71 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6'-Hydroxyenterolactone (NP0339405)

MOL for NP0339405 (6'-Hydroxyenterolactone)

3D MOL for NP0339405 (6'-Hydroxyenterolactone)

3D SDF for NP0339405 (6'-Hydroxyenterolactone)

3D-SDF for NP0339405 (6'-Hydroxyenterolactone)

PDB for NP0339405 (6'-Hydroxyenterolactone)

3D PDB for NP0339405 (6'-Hydroxyenterolactone)

SMILES for NP0339405 (6'-Hydroxyenterolactone)

INCHI for NP0339405 (6'-Hydroxyenterolactone)

Structure for NP0339405 (6'-Hydroxyenterolactone)

3D Structure for NP0339405 (6'-Hydroxyenterolactone)