NP-MRD: Showing NP-Card for Estradiol-17alpha 3-D-glucuronoside (NP0090903)

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Record Information

Version

2.0

Created at

2022-05-11 18:25:35 UTC

Updated at

2022-05-11 18:25:35 UTC

NP-MRD ID

NP0090903

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Estradiol-17alpha 3-D-glucuronoside

Description

Estradiol-17alpha 3-D-glucuronoside, also known as 17alpha-estradiol 3-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, estradiol-17alpha 3-D-glucuronoside is considered to be a steroid conjugate lipid molecule. Estradiol-17alpha 3-D-glucuronoside is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241200512D          

 35 39  0  0  1  0            999 V2000
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   13.4421   -7.5958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 02241200512D          

 35 39  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0090903

> <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-FNUZHIFDSA-N

> <FORMULA>
C24H32O8

> <MOLECULAR_WEIGHT>
448.5061

> <EXACT_MASS>
448.209718

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
47.425330406916174

> <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,14R,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]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>
111.91649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17α-estradiol 3-glucuronide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      40.673  -6.026   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.432 -12.659   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      27.765 -12.649   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      30.444  -9.580   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      27.783  -8.029   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      25.110  -9.559   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      25.092 -14.179   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      23.767 -11.864   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      38.738  -7.959   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      38.738  -9.499   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      37.404 -10.269   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      36.071  -9.499   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      40.195  -7.490   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      37.404  -7.189   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      40.195  -9.968   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      36.071  -7.959   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      41.094  -8.729   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      37.429 -11.873   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      38.738  -6.419   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.669 -10.280   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      36.046 -12.685   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      34.657 -11.884   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      33.242  -9.411   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      33.216 -12.730   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      31.782 -10.224   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      31.769 -11.895   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      29.102 -11.884   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.108 -10.344   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      27.777  -9.569   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      26.440 -10.334   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      26.434 -11.874   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      25.098 -12.639   0.000  0.00  0.00           C+0
HETATM   33  H   UNK     0      37.437  -8.483   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      38.901 -11.030   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      36.113 -10.908   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   26   27                                                       
CONECT    3   27   31                                                       
CONECT    4   28                                                            
CONECT    5   29                                                            
CONECT    6   30                                                            
CONECT    7   32                                                            
CONECT    8   32                                                            
CONECT    9   10   13   14   19                                             
CONECT   10    9   11   15   34                                             
CONECT   11   10   12   18   33                                             
CONECT   12   11   16   20   35                                             
CONECT   13    1    9   17                                                  
CONECT   14    9   16                                                       
CONECT   15   10   17                                                       
CONECT   16   12   14                                                       
CONECT   17   13   15                                                       
CONECT   18   11   21                                                       
CONECT   19    9                                                            
CONECT   20   12   22   23                                                  
CONECT   21   18   22                                                       
CONECT   22   20   21   24                                                  
CONECT   23   20   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   26                                                       
CONECT   26    2   24   25                                                  
CONECT   27    2    3   28                                                  
CONECT   28    4   27   29                                                  
CONECT   29    5   28   30                                                  
CONECT   30    6   29   31                                                  
CONECT   31    3   30   32                                                  
CONECT   32    7    8   31                                                  
CONECT   33   11                                                            
CONECT   34   10                                                            
CONECT   35   12                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
17alpha-Estradiol 3-glucuronide	ChEBI
17a-Estradiol 3-glucuronide	Generator
17Α-estradiol 3-glucuronide	Generator
Estradiol-17a 3-D-glucuronoside	Generator
Estradiol-17α 3-D-glucuronoside	Generator
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-[[(17R)-17-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-yl]oxy]tetrahydropyran-2-carboxylic acid	HMDB
17a-Estradiol 3-glucosiduronate	HMDB
17a-Estradiol 3-glucosiduronic acid	HMDB
17a-Hydroxyestra-1,3,5(10)-trien-3-yl b-D-glucopyranosiduronate	HMDB
17a-Hydroxyestra-1,3,5(10)-trien-3-yl b-D-glucopyranosiduronic acid	HMDB
17a-Hydroxyestra-1,3,5(10)-trien-3-yl b-delta-glucopyranosiduronate	HMDB
17a-Hydroxyestra-1,3,5(10)-trien-3-yl b-delta-glucopyranosiduronic acid	HMDB
17alpha-Estradiol 3-glucosiduronate	HMDB
17alpha-Estradiol 3-glucosiduronic acid	HMDB
17alpha-Hydroxyestra-1,3,5(10)-trien-3-yl beta-D-glucopyranosiduronate	HMDB
17alpha-Hydroxyestra-1,3,5(10)-trien-3-yl beta-D-glucopyranosiduronic acid	HMDB
17alpha-Hydroxyestra-1,3,5(10)-trien-3-yl beta-delta-glucopyranosiduronate	HMDB
17alpha-Hydroxyestra-1,3,5(10)-trien-3-yl beta-delta-glucopyranosiduronic acid	HMDB
Estradiol-17a 3-delta-glucuronoside	HMDB
Estradiol-17alpha 3-delta-glucuronoside	HMDB
Estradiol-17alpha 3-D-glucuronoside	ChEBI
17Α-estradiol 3-glucosiduronate	Generator
17Α-estradiol 3-glucosiduronic acid	Generator

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,14R,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-5-yl]oxy}oxane-2-carboxylic acid

Traditional Name

17α-estradiol 3-glucuronide

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-FNUZHIFDSA-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
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
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

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:15822 )
Glucuronides (LMST05010026 )

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	47.43 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

HMDB0010349

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB027501

KNApSAcK ID

Not Available

Chemspider ID

10160731

KEGG Compound ID

C04300

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11988264

PDB ID

Not Available

ChEBI ID

15822

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Estradiol-17alpha 3-D-glucuronoside (NP0090903)

MOL for NP0090903 (Estradiol-17alpha 3-D-glucuronoside)

3D MOL for NP0090903 (Estradiol-17alpha 3-D-glucuronoside)

3D SDF for NP0090903 (Estradiol-17alpha 3-D-glucuronoside)

3D-SDF for NP0090903 (Estradiol-17alpha 3-D-glucuronoside)

PDB for NP0090903 (Estradiol-17alpha 3-D-glucuronoside)

3D PDB for NP0090903 (Estradiol-17alpha 3-D-glucuronoside)

SMILES for NP0090903 (Estradiol-17alpha 3-D-glucuronoside)

INCHI for NP0090903 (Estradiol-17alpha 3-D-glucuronoside)

Structure for NP0090903 (Estradiol-17alpha 3-D-glucuronoside)

3D Structure for NP0090903 (Estradiol-17alpha 3-D-glucuronoside)