NP-MRD: Showing NP-Card for 17b-Estradiol 3-glucuronide (NP0086531)

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Record Information

Version

2.0

Created at

2022-05-11 16:23:30 UTC

Updated at

2022-05-11 16:23:30 UTC

NP-MRD ID

NP0086531

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17b-Estradiol 3-glucuronide

Description

17-Beta-Estradiol-3-glucuronide, also known as 17β-estradiol 3-glucosiduronate or estradiol-17β-3-(β-D-glucuronide), belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton. Thus, 17-beta-estradiol-3-glucuronide is considered to be a steroid conjugate lipid molecule. A steroid glucosiduronic acid that consists of 17beta-estradiol having a beta-glucuronyl residue attached at position 3 via a glycosidic linkage. 17-Beta-Estradiol-3-glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 17-beta-Estradiol-3-glucuronide is found, on average, in the highest concentration within milk (cow). 17b-Estradiol 3-glucuronide is found in Homo sapiens and Mus musculus. 17b-Estradiol 3-glucuronide was first documented in 1999 (PMID: 10365435). This could make 17-beta-estradiol-3-glucuronide a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652303062020182D          

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M  END

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M  END
> <DATABASE_ID>
NP0086531

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-17(24)25)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-21,23,25-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,17+,18+,19+,20-,21+,23-,24+/m1/s1

> <INCHI_KEY>
MUOHJTRCBBDUOW-QXYWQCSFSA-N

> <FORMULA>
C24H32O8

> <MOLECULAR_WEIGHT>
448.5061

> <EXACT_MASS>
448.209718

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
48.13253863462879

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.46

> <JCHEM_LOGP>
1.7977077730000004

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.216821230699406

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3003535897009564

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8838739528848581

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
111.91649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0      -1.185  -1.740   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.185  -0.200   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.149   0.570   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.149  -2.510   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.483  -1.740   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.816  -2.510   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.150  -1.740   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.150  -0.200   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.484   0.570   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.948   0.094   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.853   1.340   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.948   2.586   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.424   4.050   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.484   2.110   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.484   3.650   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.150   2.880   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.816   2.110   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.816   0.570   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.483  -0.200   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.519  -2.510   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.852  -1.740   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.186  -2.510   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.186  -4.050   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -6.520  -1.740   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -7.853  -2.510   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.520  -0.200   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -7.853   0.570   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.186   0.570   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.852  -0.200   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -5.186   2.110   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.520   2.880   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -3.852   2.880   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       2.816  -0.970   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.150   1.340   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.484  -0.970   0.000  0.00  0.00           H+0
CONECT    1    2    4   20                                                  
CONECT    2    1    3                                                       
CONECT    3    2   19                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   18   34                                             
CONECT    9    8   10   14   35                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    9   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    8   19   33                                             
CONECT   19   18    3    5                                                  
CONECT   20   21    1                                                       
CONECT   21   20   22   29                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28   21                                                       
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   18                                                            
CONECT   34    8                                                            
CONECT   35    9                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
17beta-Estradiol 3-(beta-D-glucuronide)	ChEBI
17beta-Estradiol 3-glucuronide	ChEBI
Estradiol-17beta 3-glucuronide	ChEBI
Estradiol-3-glucuronide	ChEBI
17b-Estradiol 3-(b-D-glucuronide)	Generator
17Β-estradiol 3-(β-D-glucuronide)	Generator
17b-Estradiol 3-glucuronide	Generator
17Β-estradiol 3-glucuronide	Generator
Estradiol-17b 3-glucuronide	Generator
Estradiol-17β 3-glucuronide	Generator
17-b-Estradiol-3-glucuronide	Generator
17-Β-estradiol-3-glucuronide	Generator
(17beta)-17-Hydroxyestra-1,3,5(10)-trien-3-yl beta-D-glucopyranosiduronic acid	HMDB
(17Β)-17-hydroxyestra-1,3,5(10)-trien-3-yl β-D-glucopyranosiduronic acid	HMDB
17beta-Estradiol 3-glucosiduronate	HMDB
17Β-estradiol 3-glucosiduronate	HMDB
Estradiol 3-glucosiduronate	HMDB
Estradiol 3-glucuronide	HMDB
Estradiol-17beta-3-(beta-D-glucuronide)	HMDB
Estradiol-17β-3-(β-D-glucuronide)	HMDB

Chemical Formula

C₂₄H₃₂O₈

Average Mass

448.5061 Da

Monoisotopic Mass

448.20972 Da

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl]oxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C=C3

InChI Identifier

InChI=1S/C24H32O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-17(24)25)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-21,23,25-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,17+,18+,19+,20-,21+,23-,24+/m1/s1

InChI Key

MUOHJTRCBBDUOW-QXYWQCSFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroid glucuronide conjugates

Alternative Parents

Substituents

Steroid-glucuronide-skeleton
Estrane-skeleton
Hydroxysteroid
17-hydroxysteroid
Fatty acyl glycoside
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
1-o-glucuronide
O-glucuronide
Phenanthrene
Glucuronic acid or derivatives
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
Tetralin
Beta-hydroxy acid
Fatty acyl
Pyran
Benzenoid
Oxane
Monosaccharide
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Acetal
Monocarboxylic acid or derivatives
Oxacycle
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

steroid glucosiduronic acid (CHEBI:36489 )
C18 steroids (estrogens) and derivatives (C05503 )
Glucuronides (C05503 )
Glucuronides (LMST05010007 )

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	1.46	ALOGPS
logP	1.8	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	111.92 m³·mol⁻¹	ChemAxon
Polarizability	48.13 Å³	ChemAxon
Number of Rings	5	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

HMDB0006224

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021792

KNApSAcK ID

Not Available

Chemspider ID

389587

KEGG Compound ID

C05503

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440713

PDB ID

Not Available

ChEBI ID

36489

Good Scents ID

Not Available

References

General References

Panter GH, Thompson RS, Beresford N, Sumpter JP: Transformation of a non-oestrogenic steroid metabolite to an oestrogenically active substance by minimal bacterial activity. Chemosphere. 1999 Jun;38(15):3579-96. doi: 10.1016/s0045-6535(98)00572-4. [PubMed:10365435 ]

Showing NP-Card for 17b-Estradiol 3-glucuronide (NP0086531)

MOL for NP0086531 (17b-Estradiol 3-glucuronide)

3D MOL for NP0086531 (17b-Estradiol 3-glucuronide)

3D SDF for NP0086531 (17b-Estradiol 3-glucuronide)

3D-SDF for NP0086531 (17b-Estradiol 3-glucuronide)

PDB for NP0086531 (17b-Estradiol 3-glucuronide)

3D PDB for NP0086531 (17b-Estradiol 3-glucuronide)

SMILES for NP0086531 (17b-Estradiol 3-glucuronide)

INCHI for NP0086531 (17b-Estradiol 3-glucuronide)

Structure for NP0086531 (17b-Estradiol 3-glucuronide)

3D Structure for NP0086531 (17b-Estradiol 3-glucuronide)