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Showing NP-Card for 5-Hydroxyenterolactone (NP0339404)

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Record Information
Version2.0
Created at2024-09-11 21:40:24 UTC
Updated at2024-09-11 21:40:25 UTC
NP-MRD IDNP0339404
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-Hydroxyenterolactone
Description 5-Hydroxyenterolactone was first documented in 2024 (PMID: 38123079). Based on a literature review very few articles have been published on 5-Hydroxyenterolactone.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339404 (5-Hydroxyenterolactone)


  Mrv2104 05272300122D          

 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
   -3.3595    1.8223    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
 15 23  1  0  0  0  0
M  END
Download

3D MOL for NP0339404 (5-Hydroxyenterolactone)

Download
3D SDF for NP0339404 (5-Hydroxyenterolactone)

  Mrv2104 05272300122D          

 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
   -3.3595    1.8223    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
 15 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339404

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(O)=CC(O)=C2)=C1

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

> <INCHI_KEY>
VZASJFJTVXPGCE-HTCGWVBYNA-N

> <FORMULA>
C18H18O5

> <MOLECULAR_WEIGHT>
314.337

> <EXACT_MASS>
314.11542368

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.84539555954537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R)-3-[(3,5-dihydroxyphenyl)methyl]-4-[(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>
9.623296337605806

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.006406239102773

> <JCHEM_PKA_STRONGEST_BASIC>
-5.670914807638063

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
84.68889999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339404 (5-Hydroxyenterolactone)
Download
PDB for NP0339404 (5-Hydroxyenterolactone)
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      -6.271   3.402   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                                                       
CONECT   11   10   12    8                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   22                                                  
CONECT   14   13    9                                                       
CONECT   15   16   20   23                                                  
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   15                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

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3D PDB for NP0339404 (5-Hydroxyenterolactone)
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SMILES for NP0339404 (5-Hydroxyenterolactone)
OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(O)=CC(O)=C2)=C1
Download
INCHI for NP0339404 (5-Hydroxyenterolactone)
InChI=1/C18H18O5/c19-14-3-1-2-11(5-14)4-13-10-23-18(22)17(13)8-12-6-15(20)9-16(21)7-12/h1-3,5-7,9,13,17,19-21H,4,8,10H2/t13-,17+/s2
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View in JSmol
SynonymsNot Available
Chemical FormulaC18H18O5
Average Mass314.3370 Da
Monoisotopic Mass314.11542 Da
IUPAC Name(3R,4R)-3-[(3,5-dihydroxyphenyl)methyl]-4-[(3-hydroxyphenyl)methyl]oxolan-2-one
Traditional Name(3R,4R)-3-[(3,5-dihydroxyphenyl)methyl]-4-[(3-hydroxyphenyl)methyl]oxolan-2-one
CAS Registry NumberNot Available
SMILES
OC1=CC=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(O)=CC(O)=C2)=C1
InChI Identifier
InChI=1/C18H18O5/c19-14-3-1-2-11(5-14)4-13-10-23-18(22)17(13)8-12-6-15(20)9-16(21)7-12/h1-3,5-7,9,13,17,19-21H,4,8,10H2/t13-,17+/s2
InChI KeyVZASJFJTVXPGCE-HTCGWVBYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound 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
    • 

  • Resorcinol
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Gamma butyrolactone
    • 

  • Tetrahydrofuran
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • 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
logP3.3ChemAxon
pKa (Strongest Acidic)9.01ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity84.69 m³·mol⁻¹ChemAxon
Polarizability31.85 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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Fu Q, Qiu Y, Zhao J, Li J, Xie S, Liao Q, Fu X, Huang Y, Yao Z, Dai Z, Qiu Y, Yang Y, Li F, Chen H: Monotonic trends of soil microbiomes, metagenomic and metabolomic functioning across ecosystems along water gradients in the Altai region, northwestern China. Sci Total Environ. 2024 Feb 20;912:169351. doi: 10.1016/j.scitotenv.2023.169351.  Epub 2023 Dec 18. [PubMed:38123079  ]