NP-MRD: Showing NP-Card for Estradiol acetate glucuronide (NP0136318)

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Record Information

Version

2.0

Created at

2022-05-12 15:11:27 UTC

Updated at

2022-05-12 15:11:27 UTC

NP-MRD ID

NP0136318

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Estradiol acetate glucuronide

Description

Estradiol acetate 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. Estradiol acetate glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304062013172D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304062013172D          

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M  END
> <DATABASE_ID>
NP0136318

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CCC2C3CCC4=C(C=CC(OC5OC(C(O)C(O)C5O)C(O)=O)=C4)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O9/c1-12(27)33-19-8-7-18-17-5-3-13-11-14(4-6-15(13)16(17)9-10-26(18,19)2)34-25-22(30)20(28)21(29)23(35-25)24(31)32/h4,6,11,16-23,25,28-30H,3,5,7-10H2,1-2H3,(H,31,32)

> <INCHI_KEY>
UJWWCALEXRYEBV-UHFFFAOYSA-N

> <FORMULA>
C26H34O9

> <MOLECULAR_WEIGHT>
490.5428

> <EXACT_MASS>
490.220282686

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.55221728999761

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{[14-(acetyloxy)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.238833183333334

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.216821230699374

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3003251781516494

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868267622517834

> <JCHEM_POLAR_SURFACE_AREA>
142.75000000000003

> <JCHEM_REFRACTIVITY>
121.06799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{[14-(acetyloxy)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0       0.055   1.210   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.279   0.440   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.279  -1.100   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.055  -1.870   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.389  -1.100   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.389   0.440   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.722  -1.870   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.056  -1.100   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.056   0.440   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.722   1.210   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.722   2.750   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.056   3.520   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.390   2.750   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.828   3.302   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.390   1.210   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.958   0.813   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.797   2.105   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.226   4.789   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.714   5.188   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.484   6.522   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.484   3.854   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.390   4.290   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.612  -1.870   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -3.946  -1.100   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.946   0.440   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.279   1.210   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.613   0.440   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.613  -1.100   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -5.279  -1.870   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -5.279   2.750   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -7.947   1.210   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -7.947  -1.870   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -9.281  -1.100   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -7.947  -3.410   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -2.612   1.210   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    7    6                                                  
CONECT    6    1    5   10                                                  
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   15   10                                                  
CONECT   10    6    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   22                                             
CONECT   14   13   17   18                                                  
CONECT   15    9   16   13                                                  
CONECT   16   15   17                                                       
CONECT   17   14   16                                                       
CONECT   18   14   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   13                                                            
CONECT   23    3   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26   35                                                  
CONECT   26   25   27   30                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29   32                                                  
CONECT   29   24   28                                                       
CONECT   30   26                                                            
CONECT   31   27                                                            
CONECT   32   28   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   25                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Estradiol acetic acid glucuronide	Generator

Chemical Formula

C₂₆H₃₄O₉

Average Mass

490.5428 Da

Monoisotopic Mass

490.22028 Da

IUPAC Name

6-{[14-(acetyloxy)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

6-{[14-(acetyloxy)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CCC2C3CCC4=C(C=CC(OC5OC(C(O)C(O)C5O)C(O)=O)=C4)C3CCC12C

InChI Identifier

InChI=1S/C26H34O9/c1-12(27)33-19-8-7-18-17-5-3-13-11-14(4-6-15(13)16(17)9-10-26(18,19)2)34-25-22(30)20(28)21(29)23(35-25)24(31)32/h4,6,11,16-23,25,28-30H,3,5,7-10H2,1-2H3,(H,31,32)

InChI Key

UJWWCALEXRYEBV-UHFFFAOYSA-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

Not Available

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
Steroid ester
Estrane-skeleton
Fatty acyl glycoside
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
1-o-glucuronide
O-glucuronide
Phenanthrene
Glucuronic acid or derivatives
Alkyl glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Tetralin
Beta-hydroxy acid
Fatty acyl
Benzenoid
Pyran
Oxane
Dicarboxylic acid or derivatives
Monosaccharide
Hydroxy acid
Secondary alcohol
Carboxylic acid ester
Carboxylic acid
Oxacycle
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Acetal
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Alcohol
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	2.17	ALOGPS
logP	2.24	ChemAxon
logS	-3.6	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	142.75 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.07 m³·mol⁻¹	ChemAxon
Polarizability	51.55 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0061687

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

131770405

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Estradiol acetate glucuronide (NP0136318)

MOL for NP0136318 (Estradiol acetate glucuronide)

3D MOL for NP0136318 (Estradiol acetate glucuronide)

3D SDF for NP0136318 (Estradiol acetate glucuronide)

3D-SDF for NP0136318 (Estradiol acetate glucuronide)

PDB for NP0136318 (Estradiol acetate glucuronide)

3D PDB for NP0136318 (Estradiol acetate glucuronide)

SMILES for NP0136318 (Estradiol acetate glucuronide)

INCHI for NP0136318 (Estradiol acetate glucuronide)

Structure for NP0136318 (Estradiol acetate glucuronide)

3D Structure for NP0136318 (Estradiol acetate glucuronide)