NP-MRD: Showing NP-Card for estrone 3-glucuronide (NP0191360)

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Record Information

Version

2.0

Created at

2022-09-04 08:17:38 UTC

Updated at

2022-09-04 08:17:38 UTC

NP-MRD ID

NP0191360

Secondary Accession Numbers

None

Natural Product Identification

Common Name

estrone 3-glucuronide

Description

Estrone 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, estrone glucuronide is considered to be a steroid conjugate lipid molecule. Estrone glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Estrone glucuronide and uridine 5'-diphosphate can be biosynthesized from estrone and uridine diphosphate glucuronic acid through the action of the enzyme UDP-glucuronosyltransferase 1-1. In humans, estrone glucuronide is involved in estrone metabolism. estrone 3-glucuronide is found in Apis cerana, Homo sapiens and Mus musculus. estrone 3-glucuronide was first documented in 2010 (PMID: 20541211). The 3-beta-D-glucuronide of estrone.

Structure

MOL 3D MOL SDF PDB SMILES InChI

HMDB04483.mol
  Mrv0541 02231219562D          

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M  END

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HMDB04483.mol
  Mrv0541 02231219562D          

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M  END
> <DATABASE_ID>
NP0191360

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C3CC[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O8/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/h3,5,10,14-16,18-21,23,26-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,18+,19+,20-,21+,23-,24+/m1/s1

> <INCHI_KEY>
FJAZVHYPASAQKM-JBAURARKSA-N

> <FORMULA>
C24H30O8

> <MOLECULAR_WEIGHT>
446.4902

> <EXACT_MASS>
446.194067936

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
46.77478379122559

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
2.361235478666667

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.216821222809472

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.300315342672925

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868267622517834

> <JCHEM_POLAR_SURFACE_AREA>
133.51999999999998

> <JCHEM_REFRACTIVITY>
111.09419999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
estrone-3-glucuronide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB04483.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.185  -0.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.185  -1.740   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.149  -2.510   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.483  -1.740   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.483  -0.200   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.149   0.570   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.816  -2.510   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.150  -1.740   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.150  -0.200   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.816   0.570   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.484   0.570   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.484   2.110   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.150   2.880   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.816   2.110   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.948   0.094   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.853   1.340   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.948   2.586   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.520  -0.200   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.520  -1.740   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.186  -2.510   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.852  -1.740   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.852  -0.201   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.186   0.570   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.186   2.110   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.519  -2.510   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -7.853  -2.510   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -7.853   0.570   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -5.186  -4.050   0.000  0.00  0.00           O+0
HETATM   29  H   UNK     0       1.483   1.340   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.484  -0.970   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.150   1.340   0.000  0.00  0.00           H+0
HETATM   32  O   UNK     0       7.424   4.050   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.644   3.641   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.852   2.880   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -6.520   2.880   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   25                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   31                                             
CONECT   10    9    5   14   29                                             
CONECT   11    9   12   15   30                                             
CONECT   12   11   13   17   33                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   32                                                  
CONECT   18   19   23   27                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23   34   35                                                  
CONECT   25   21    2                                                       
CONECT   26   19                                                            
CONECT   27   18                                                            
CONECT   28   20                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31    9                                                            
CONECT   32   17                                                            
CONECT   33   12                                                            
CONECT   34   24                                                            
CONECT   35   24                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Estrone 3-glucosiduronic acid	ChEBI
Estrone 3-glucuronide	ChEBI
Estrone beta-D-glucuronide	ChEBI
Estrone 3-glucosiduronate	Generator
Estrone b-D-glucuronide	Generator
Estrone β-D-glucuronide	Generator
Estrone beta-delta-glucuronide	HMDB
Estrone-3-glucosiduronic acid	HMDB
Estrone-3-glucuronide	HMDB
Estrone-3-glucosiduronate	HMDB

Chemical Formula

C₂₄H₃₀O₈

Average Mass

446.4902 Da

Monoisotopic Mass

446.19407 Da

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylic acid

Traditional Name

estrone-3-glucuronide

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C24H30O8/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/h3,5,10,14-16,18-21,23,26-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,18+,19+,20-,21+,23-,24+/m1/s1

InChI Key

FJAZVHYPASAQKM-JBAURARKSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Apis cerana	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C18 steroids (estrogens) and derivatives (C11133 )
Glucuronides (C11133 )
Glucuronides (LMST05010011 )

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	1.92	ALOGPS
logP	2.36	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	111.09 m³·mol⁻¹	ChemAxon
Polarizability	46.77 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

HMDB0004483

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021803

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Good Scents ID

Not Available

References

General References

Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024. Epub 2010 May 25. [PubMed:20541211 ]
LOTUS database [Link]

Showing NP-Card for estrone 3-glucuronide (NP0191360)

MOL for NP0191360 (estrone 3-glucuronide)

3D MOL for NP0191360 (estrone 3-glucuronide)

3D SDF for NP0191360 (estrone 3-glucuronide)

3D-SDF for NP0191360 (estrone 3-glucuronide)

PDB for NP0191360 (estrone 3-glucuronide)

3D PDB for NP0191360 (estrone 3-glucuronide)

SMILES for NP0191360 (estrone 3-glucuronide)

INCHI for NP0191360 (estrone 3-glucuronide)

Structure for NP0191360 (estrone 3-glucuronide)

3D Structure for NP0191360 (estrone 3-glucuronide)