NP-MRD: Showing NP-Card for Enterolactone (NP0050469)

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Record Information

Version

2.0

Created at

2022-04-27 21:44:38 UTC

Updated at

2022-04-27 21:44:38 UTC

NP-MRD ID

NP0050469

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Enterolactone

Description

Enterolactone, also known as HPMF or BHMDF, belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Enterolactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Enterolactone and lignans may also be protective against cardiovascular disease. Antibiotic treatments can abolish the capacity to produce enterolactone. Enterolactone is a chemical compound formed by the action of intestinal bacteria on plant lignan precursors present in the diet. The richest known dietary sources of enterolactone precursors are flaxseed and sesame seed. In edible plants lignans are bound to the fiber fraction and therefore fiber-rich food products, such as cereals, vegetables, fruits and berries, are generally good sources of lignans and enterolactone. Many dietary plant lignan precursors, such as secoisolariciresinol, matairesinol, lariciresinol, pinoresinol, and sesamin, can be metabolized by gut microbes to enterolactone. Since enterolactone is produced by specific species of gut microbiota, the capacity to produce it varies between people. It may take up to a year before enterolactone production is restored. Enterolactone is suggested to possess beneficial health effects in humans. Enterolactone is found in Homo Sapiens, Mammalian lignana, Urtica dioica and Zingiber zerumbet. Enterolactone was first documented in 2002 (PMID: 12270221). In epidemiological studies lower concentrations of enterolactone have been observed in breast cancer patients compared to healthy controls, which may suggest that enterolactone is anti-carcinogenic (PMID: 16168401).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307191923442D          

 22 24  0  0  0  0            999 V2000
10001.1086 9999.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.9601 9999.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8517 9999.1426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.9998 9999.1426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.545110000.5782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.991510000.8194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.324110000.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5790 9999.5498    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.4040 9999.5498    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.658910000.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.140210000.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.425810000.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.711310000.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7112 9999.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4257 9999.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1403 9999.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.534710000.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.820310000.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8203 9999.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5347 9999.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2492 9999.5538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.249210000.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  9  1  1  1  0  0  0
  8  3  1  6  0  0  0
  7  5  2  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
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 11  1  0  0  0  0
  3 16  1  0  0  0  0
 14  4  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 17  1  0  0  0  0
  1 19  1  0  0  0  0
 21  2  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050469

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m1/s1

> <INCHI_KEY>
HVDGDHBAMCBBLR-PBHICJAKSA-N

> <FORMULA>
C18H18O4

> <MOLECULAR_WEIGHT>
298.338

> <EXACT_MASS>
298.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.942419359849175

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4S)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
3.607125042333333

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.765099955610825

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.163039070788626

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9640436366683405

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
82.70800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
enterolactone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0    8668.7368665.066   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8674.0598665.066   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8664.5238665.066   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8659.2008665.066   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8663.9518667.746   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8666.6518668.196   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8665.4058667.291   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.8818665.826   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8667.4218665.826   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.8978667.291   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8663.1958667.374   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.8618668.144   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8660.5288667.374   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.5288665.834   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8661.8618665.064   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8663.1958665.834   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8671.3988668.144   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.0658667.374   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8670.0658665.834   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8671.3988665.064   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.7328665.834   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8672.7328667.374   0.000  0.00  0.00           C+0
CONECT    1    9   19                                                       
CONECT    2   21                                                            
CONECT    3    8   16                                                       
CONECT    4   14                                                            
CONECT    5    7                                                            
CONECT    6    7   10                                                       
CONECT    7    8    6    5                                                  
CONECT    8    7    9    3                                                  
CONECT    9    8   10    1                                                  
CONECT   10    9    6                                                       
CONECT   11   12   16                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15    4                                                  
CONECT   15   14   16                                                       
CONECT   16   15   11    3                                                  
CONECT   17   18   22                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20    1                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22    2                                                  
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
2,3-Bis(3'-hydroxybenzyl)butyrolactone	HMDB
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-isomer	HMDB
HPMF	HMDB
trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactone	HMDB
BHMDF	HMDB
2,3-BHBB	HMDB
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-(+-)-isomer	HMDB
3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanone	HMDB
(+)-Enterolactone	HMDB
(3S)-trans-Enterolactone	HMDB
(3S,4S)-Dihydro-3,4-bis[(3-hydroxyphenyl)methyl]-2(3H)-furanone	HMDB
(3S,4S)-Enterolactone	HMDB
(±)-enterolactone	HMDB
2,3-Bis(3’-hydroxybenzyl)butyrolactone	HMDB
trans-2,3-Bis(3-hydroxybenzyl)-γ-butyrolactone	HMDB
Enterolactone	HMDB

Chemical Formula

C₁₈H₁₈O₄

Average Mass

298.3380 Da

Monoisotopic Mass

298.12051 Da

IUPAC Name

(3S,4S)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one

Traditional Name

enterolactone

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17+/m1/s1

InChI Key

HVDGDHBAMCBBLR-PBHICJAKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	Animalia	KNApSAcK
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Mammalian lignana	-	KNApSAcK
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Urtica dioica	LOTUS Database	35616633
Zingiber zerumbet	LOTUS Database	35616633

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.

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
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

lignan (CHEBI:81555 )

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	3.2	ALOGPS
logP	3.61	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.71 m³·mol⁻¹	ChemAxon
Polarizability	30.94 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

HMDB0006101

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000703

Chemspider ID

Not Available

KEGG Compound ID

C18165

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Enterolactone

METLIN ID

Not Available

PubChem Compound

114739

PDB ID

Not Available

ChEBI ID

81555

Good Scents ID

Not Available

References

General References

Wang LQ: Mammalian phytoestrogens: enterodiol and enterolactone. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):289-309. doi: 10.1016/s1570-0232(02)00281-7. [PubMed:12270221 ]
Boccardo F, Puntoni M, Guglielmini P, Rubagotti A: Enterolactone as a risk factor for breast cancer: a review of the published evidence. Clin Chim Acta. 2006 Mar;365(1-2):58-67. doi: 10.1016/j.cca.2005.07.026. Epub 2005 Sep 15. [PubMed:16168401 ]

Showing NP-Card for Enterolactone (NP0050469)

MOL for NP0050469 (Enterolactone)

3D MOL for NP0050469 (Enterolactone)

3D SDF for NP0050469 (Enterolactone)

3D-SDF for NP0050469 (Enterolactone)

PDB for NP0050469 (Enterolactone)

3D PDB for NP0050469 (Enterolactone)

SMILES for NP0050469 (Enterolactone)

INCHI for NP0050469 (Enterolactone)

Structure for NP0050469 (Enterolactone)

3D Structure for NP0050469 (Enterolactone)