NP-MRD: Showing NP-Card for Estriol-16-glucuronide (NP0087628)

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Record Information

Version

2.0

Created at

2022-05-11 16:55:13 UTC

Updated at

2022-05-11 16:55:13 UTC

NP-MRD ID

NP0087628

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Estriol-16-glucuronide

Description

Estriol-16-Glucuronide, also known as 16-glucuronide-estriol, 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. Thus, estriol-16-glucuronide is considered to be a steroid conjugate lipid molecule. Estriol-16-glucuronide is found in Mus musculus. Estriol-16-glucuronide was first documented in 1976 (PMID: 1263497). Estriol-16-Glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 16586468) (PMID: 16414729) (PMID: 190739) (PMID: 192950).

Structure

MOL 3D MOL SDF PDB SMILES InChI

 
  Mrv0541 02231220512D          

 33 37  0  0  1  0            999 V2000
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    2.6190   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END

 
  Mrv0541 02231220512D          

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M  END
> <DATABASE_ID>
NP0087628

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(O)=C4)[C@@H]1C[C@@H](O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)[C@@H]2O

> <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(21(24)29)32-23-19(28)17(26)18(27)20(33-23)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+/m1/s1

> <INCHI_KEY>
FQYGGFDZJFIDPU-JRSYHJKYSA-N

> <FORMULA>
C24H32O9

> <MOLECULAR_WEIGHT>
464.5055

> <EXACT_MASS>
464.204632622

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
48.42230571826707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.220036613666667

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.321463239537326

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.457276818780923

> <JCHEM_PKA_STRONGEST_BASIC>
-3.346062051897775

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
113.5469

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.397  -0.314   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.882  -1.480   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      10.813   1.738   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.991   0.746   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.439   1.269   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.616   0.276   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.345  -1.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.897  -1.763   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.719  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      12.626  -3.279   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.177  -3.802   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.803  -4.272   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      15.522  -2.233   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      16.065   0.799   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      13.710   2.785   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.811   2.218   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   10                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   28                                                  
CONECT    6    5    7   25                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9    2   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16                                                            
CONECT   23   15                                                            
CONECT   24   14                                                            
CONECT   25    6   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   32                                                  
CONECT   28   27    5   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31   27                                                       
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

View in JSmol

Synonyms

Value	Source
16-Glucuronide-estriol	ChEBI
16alpha,17beta-Estriol 16-(beta-D-glucuronide)	ChEBI
16alpha,17beta-Estriol 16-O-(beta-D-glucuronide)	ChEBI
Estra-1,3,5(10)-triene-3,16alpha,17beta-triol 16-D-glucuronide	ChEBI
Estriol-16-glucosiduronate	ChEBI
Estriol-16alpha-glucuronide	ChEBI
Oestriol-16alpha-glucuronide	ChEBI
16a,17b-Estriol 16-(b-D-glucuronide)	Generator
16Α,17β-estriol 16-(β-D-glucuronide)	Generator
16a,17b-Estriol 16-O-(b-D-glucuronide)	Generator
16Α,17β-estriol 16-O-(β-D-glucuronide)	Generator
Estra-1,3,5(10)-triene-3,16a,17b-triol 16-D-glucuronide	Generator
Estra-1,3,5(10)-triene-3,16α,17β-triol 16-D-glucuronide	Generator
Estriol-16-glucosiduronic acid	Generator
Estriol-16a-glucuronide	Generator
Estriol-16α-glucuronide	Generator
Oestriol-16a-glucuronide	Generator
Oestriol-16α-glucuronide	Generator
16alpha,17beta-Estriol 16-(beta-delta-glucuronide)	HMDB
Estriol-16 alpha-(beta-D-glucuronide)	HMDB
Estriol-16 alpha-(beta-D-glucuronide), sodium salt	HMDB
Estriol-16-(beta-D-glucuronide), (16beta,17beta)-isomer	HMDB
3,17 beta-Dihydroxy-1,3,5(10)-estratrien-16 alpha-yl-beta-D-glucopyranosiduronic acid	HMDB
Estriol-16 alpha-glucuronide	HMDB

Chemical Formula

C₂₄H₃₂O₉

Average Mass

464.5055 Da

Monoisotopic Mass

464.20463 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=C3C=CC(O)=C4)[C@@H]1C[C@@H](O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)[C@@H]2O

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(21(24)29)32-23-19(28)17(26)18(27)20(33-23)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+/m1/s1

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

steroid saponin (CHEBI:766 )
C18 steroids (estrogens) and derivatives (C05504 )
Glucuronides (C05504 )
Glucuronides (LMST05010008 )

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	1.03	ALOGPS
logP	1.22	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	-3.3	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	48.42 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

HMDB0006766

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB024069

KNApSAcK ID

Not Available

Chemspider ID

109041

KEGG Compound ID

C05504

BioCyc ID

Not Available

BiGG ID

45936

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122281

PDB ID

Not Available

ChEBI ID

766

Good Scents ID

Not Available

References

General References

Lampinen-Salomonsson M, Bondesson U, Petersson C, Hedeland M: Differentiation of estriol glucuronide isomers by chemical derivatization and electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(9):1429-40. doi: 10.1002/rcm.2463. [PubMed:16586468 ]
Adlercreutz H, Lehtinen T, Tikkanen M: Preliminary studies on the determination of estriol-16alpha-glucuronide in pregnancy urine by direct radioimmunoassay without hydrolysis. J Steroid Biochem. 1976 Feb;7(2):105-7. doi: 10.1016/0022-4731(76)90143-6. [PubMed:1263497 ]
Sher A, Rahman A: Effect of rifampicin on the enterohepatic recycling of estrogen in female tuberculous patients. Pak J Pharm Sci. 1993 Jan;6(1):67-79. [PubMed:16414729 ]
Musey PI, Collins DC, Preedy JR: Estrogen metabolism in nonhuman primates. I. In vitro biosynthesis of estrogen glucosiduronates in rhesus monkey liver. Steroids. 1977 Jan;29(1):93-104. doi: 10.1016/0039-128x(77)90112-x. [PubMed:190739 ]
Lehtinen T, Adlerceutz H: Solid-phase radioimmunoassays of estriol-16alpha-glucuronide in urine and pregnancy plasma. J Steroid Biochem. 1977 Jan;8(1):99-104. doi: 10.1016/0022-4731(77)90223-0. [PubMed:192950 ]

Showing NP-Card for Estriol-16-glucuronide (NP0087628)

MOL for NP0087628 (Estriol-16-glucuronide)

3D MOL for NP0087628 (Estriol-16-glucuronide)

3D SDF for NP0087628 (Estriol-16-glucuronide)

3D-SDF for NP0087628 (Estriol-16-glucuronide)

PDB for NP0087628 (Estriol-16-glucuronide)

3D PDB for NP0087628 (Estriol-16-glucuronide)

SMILES for NP0087628 (Estriol-16-glucuronide)

INCHI for NP0087628 (Estriol-16-glucuronide)

Structure for NP0087628 (Estriol-16-glucuronide)

3D Structure for NP0087628 (Estriol-16-glucuronide)