NP-MRD: Showing NP-Card for Estriol-17-glucuronide (NP0090888)

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Record Information

Version

2.0

Created at

2022-05-11 18:25:09 UTC

Updated at

2022-05-11 18:25:09 UTC

NP-MRD ID

NP0090888

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Estriol-17-glucuronide

Description

Estriol-17-glucuronide belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. Estriol-17-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241200502D          

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M  END

     RDKit          3D

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  Mrv0541 02241200502D          

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M  END
> <DATABASE_ID>
NP0090888

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@@H](O)[C@H](OC3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@]1(C)CC[C@@]1([H])C3=C(CC[C@]21[H])C=C(O)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(25)8-10(12)2-4-14(13)15(24)9-16(26)21(24)33-23-19(29)17(27)18(28)20(32-23)22(30)31/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)/t13-,14-,15+,16+,17-,18-,19+,20-,21-,23?,24-/m0/s1

> <INCHI_KEY>
CZGFLAQOJPXVRV-GITAKMRZSA-N

> <FORMULA>
C24H32O9

> <MOLECULAR_WEIGHT>
464.5055

> <EXACT_MASS>
464.204632622

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
48.50565948635248

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R)-6-{[(1R,10S,11R,13R,14R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
1.220036613666667

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.321563192381923

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5470418792688974

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1633806628316394

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
113.54689999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R)-6-{[(1R,10S,11R,13R,14R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <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      34.936  -9.294   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      36.896 -11.997   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      37.471 -10.123   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      35.893  -6.366   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      38.907  -5.731   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      24.695 -15.928   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      40.964  -8.024   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      39.529 -12.415   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      41.514 -10.634   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      33.000 -11.227   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      33.000 -12.767   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.667 -13.537   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.458 -10.758   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      30.333 -12.767   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      34.458 -13.237   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.667 -10.457   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      35.357 -11.997   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.333 -11.227   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.692 -15.141   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.000  -9.687   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.932 -13.548   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      30.309 -15.954   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.919 -15.152   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      36.443  -8.976   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      27.504 -12.679   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      27.479 -15.998   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      36.922  -7.513   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.045 -13.492   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      38.429  -7.195   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      26.032 -15.163   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      38.979  -9.805   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      39.457  -8.341   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      40.007 -10.951   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0      33.139 -14.069   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      31.548 -11.950   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      30.414 -14.525   0.000  0.00  0.00           H+0
CONECT    1   13   24                                                       
CONECT    2   17                                                            
CONECT    3   24   31                                                       
CONECT    4   27                                                            
CONECT    5   29                                                            
CONECT    6   30                                                            
CONECT    7   32                                                            
CONECT    8   33                                                            
CONECT    9   33                                                            
CONECT   10   11   13   16   20                                             
CONECT   11   10   12   15   34                                             
CONECT   12   11   14   19   35                                             
CONECT   13    1   10   17                                                  
CONECT   14   12   18   21   36                                             
CONECT   15   11   17                                                       
CONECT   16   10   18                                                       
CONECT   17    2   13   15                                                  
CONECT   18   14   16                                                       
CONECT   19   12   22                                                       
CONECT   20   10                                                            
CONECT   21   14   23   25                                                  
CONECT   22   19   23                                                       
CONECT   23   21   22   26                                                  
CONECT   24    1    3   27                                                  
CONECT   25   21   28                                                       
CONECT   26   23   30                                                       
CONECT   27    4   24   29                                                  
CONECT   28   25   30                                                       
CONECT   29    5   27   32                                                  
CONECT   30    6   26   28                                                  
CONECT   31    3   32   33                                                  
CONECT   32    7   29   31                                                  
CONECT   33    8    9   31                                                  
CONECT   34   11                                                            
CONECT   35   12                                                            
CONECT   36   14                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(16alpha,17beta)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-yl beta-D-glucopyranosiduronic acid	HMDB
(16alpha,17beta)-3,16-Dihydroxyestra-1,3,5(10)-trien-17-yl beta-delta-glucopyranosiduronic acid	HMDB
17beta-(beta-D-Glucopyranuronosyloxy)estra-1,3,5(10)-triene-3,16alpha-diol	HMDB
17beta-(beta-delta-Glucopyranuronosyloxy) estra-1,3,5(10)-triene-3,16alpha-diol	HMDB
17beta-(beta-delta-Glucopyranuronosyloxy)estra-1,3,5(10)-triene-3,16alpha-diol	HMDB
3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17beta-yl glucopyranosiduronic acid	HMDB
beta-D-Glucopyranosiduronic acid derivative OF estrane	HMDB
beta-delta-Glucopyranosiduronic acid derivative OF estrane	HMDB
Estriol 17-glucuronide	HMDB
Estriol 17beta-(beta-D-glucuronide)	HMDB
Estriol 17beta-(beta-delta-glucuronide)	HMDB
Estriol 17beta-glucuronide	HMDB
Estriol 17beta-monoglucuronide	HMDB

Chemical Formula

C₂₄H₃₂O₉

Average Mass

464.5055 Da

Monoisotopic Mass

464.20463 Da

IUPAC Name

(2S,3S,4S,5R)-6-{[(1R,10S,11R,13R,14R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R)-6-{[(1R,10S,11R,13R,14R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@H](O)[C@H](OC3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@]1(C)CC[C@@]1([H])C3=C(CC[C@]21[H])C=C(O)C=C3

InChI Identifier

InChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(25)8-10(12)2-4-14(13)15(24)9-16(26)21(24)33-23-19(29)17(27)18(28)20(32-23)22(30)31/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)/t13-,14-,15+,16+,17-,18-,19+,20-,21-,23?,24-/m0/s1

InChI Key

CZGFLAQOJPXVRV-GITAKMRZSA-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 steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically 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

Steroidal glycosides

Alternative Parents

Substituents

Steroidal glycoside
Estrogen-skeleton
3-hydroxysteroid
Estrane-skeleton
Hydroxysteroid
16-alpha-hydroxysteroid
16-hydroxysteroid
1-o-glucuronide
O-glucuronide
Phenanthrene
Glucuronic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Tetralin
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Oxane
Monosaccharide
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	1.01	ALOGPS
logP	1.22	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	113.55 m³·mol⁻¹	ChemAxon
Polarizability	48.51 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB027485

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

151453

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Estriol-17-glucuronide (NP0090888)

MOL for NP0090888 (Estriol-17-glucuronide)

3D MOL for NP0090888 (Estriol-17-glucuronide)

3D SDF for NP0090888 (Estriol-17-glucuronide)

3D-SDF for NP0090888 (Estriol-17-glucuronide)

PDB for NP0090888 (Estriol-17-glucuronide)

3D PDB for NP0090888 (Estriol-17-glucuronide)

SMILES for NP0090888 (Estriol-17-glucuronide)

INCHI for NP0090888 (Estriol-17-glucuronide)

Structure for NP0090888 (Estriol-17-glucuronide)

3D Structure for NP0090888 (Estriol-17-glucuronide)