NP-MRD: Showing NP-Card for 3,17-Androstanediol glucuronide (NP0090877)

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Record Information

Version

2.0

Created at

2022-05-11 18:24:52 UTC

Updated at

2022-05-11 18:24:52 UTC

NP-MRD ID

NP0090877

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,17-Androstanediol glucuronide

Description

Ketoprofen glucuronide belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. Ketoprofen 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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 12 21  1  0  0  0  0
 12 24  1  1  0  0  0
 13 16  1  0  0  0  0
 13 19  1  0  0  0  0
 13 25  1  1  0  0  0
 14 20  1  0  0  0  0
 14 23  1  0  0  0  0
 14 37  1  6  0  0  0
 15 16  1  0  0  0  0
 17 20  1  0  0  0  0
 18 22  1  0  0  0  0
 19 22  1  0  0  0  0
 21 26  1  0  0  0  0
 23 27  1  0  0  0  0
 26 27  1  0  0  0  0
 29 28  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0090877

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](CC[C@]12C)OC(=O)[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O8/c1-24-9-7-13(32-23(31)21-19(28)18(27)20(29)22(30)33-21)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-22,26-30H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-,20+,21-,22+,24-,25-/m0/s1

> <INCHI_KEY>
TWDCYBTXSUNASK-WGGIPMEBSA-N

> <FORMULA>
C25H40O8

> <MOLECULAR_WEIGHT>
468.5803

> <EXACT_MASS>
468.272318256

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
51.30168877328737

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5R,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
1.2559632756666654

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.604392153561587

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.283208059048665

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8838726563088571

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
116.92979999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

> <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      41.039  -6.046   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      30.799 -12.679   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      29.474 -10.364   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      28.125 -14.209   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      26.806 -10.354   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      24.133 -11.883   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      24.121 -14.963   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      26.783 -16.513   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      36.436  -9.519   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.770 -10.289   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      39.104  -9.519   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.035 -10.299   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      39.104  -7.979   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.023 -11.903   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      36.436  -7.979   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.770  -7.209   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      37.795 -11.892   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      40.561  -9.988   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      40.561  -7.509   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.412 -12.705   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      33.608  -9.430   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      41.459  -8.749   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      33.582 -12.750   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      35.047  -8.759   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      39.104  -6.439   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      32.148 -10.243   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      32.135 -11.914   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      29.468 -11.904   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      28.131 -12.669   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      26.801 -11.894   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      25.464 -12.659   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      25.458 -14.198   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      26.789 -14.974   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0      36.477 -11.546   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      37.789  -8.509   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      39.234 -10.744   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0      35.027 -13.135   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2   27   28                                                       
CONECT    3   28                                                            
CONECT    4   29   33                                                       
CONECT    5   30                                                            
CONECT    6   31                                                            
CONECT    7   32                                                            
CONECT    8   33                                                            
CONECT    9   10   12   15   34                                             
CONECT   10    9   11   17   35                                             
CONECT   11   10   13   18   36                                             
CONECT   12    9   14   21   24                                             
CONECT   13   11   16   19   25                                             
CONECT   14   12   20   23   37                                             
CONECT   15    9   16                                                       
CONECT   16   13   15                                                       
CONECT   17   10   20                                                       
CONECT   18   11   22                                                       
CONECT   19    1   13   22                                                  
CONECT   20   14   17                                                       
CONECT   21   12   26                                                       
CONECT   22   18   19                                                       
CONECT   23   14   27                                                       
CONECT   24   12                                                            
CONECT   25   13                                                            
CONECT   26   21   27                                                       
CONECT   27    2   23   26                                                  
CONECT   28    2    3   29                                                  
CONECT   29    4   28   30                                                  
CONECT   30    5   29   31                                                  
CONECT   31    6   30   32                                                  
CONECT   32    7   31   33                                                  
CONECT   33    4    8   32                                                  
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
CONECT   37   14                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
1-(3-Benzoyl-alpha-methylbenzeneacetate) beta-D-glucopyranuronic acid	HMDB
1-(3-Benzoyl-alpha-methylbenzeneacetate) beta-delta-glucopyranuronic acid	HMDB
DL-Ketoprofen glucuronide	HMDB
3-alpha-Androstanediol glucuronide	MeSH, HMDB
Androstane-3,17-diol glucuronide, (3beta,5alpha,17beta)-isomer	MeSH, HMDB
5-alpha-Androstane-3 alpha,17 beta-diol glucuronide	MeSH, HMDB
Androstane-3,17-diol glucuronide, (3alpha,5beta,17beta)-isomer	MeSH, HMDB
3 alpha-Diol g	MeSH, HMDB
3-Hydroxyandrostan-17-yl-glucopyranosiduronic acid	MeSH, HMDB
(1S,2S,5R,7S,10R,11S,14S,15S)-14-Hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid	Generator
3,17-Androstanediol glucuronide	MeSH
Androstane-3,17-diol glucuronide	MeSH

Chemical Formula

C₂₅H₄₀O₈

Average Mass

468.5803 Da

Monoisotopic Mass

468.27232 Da

IUPAC Name

(1S,2S,5R,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

Traditional Name

(1S,2S,5R,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](CC[C@]12C)OC(=O)[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C25H40O8/c1-24-9-7-13(32-23(31)21-19(28)18(27)20(29)22(30)33-21)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-22,26-30H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-,20+,21-,22+,24-,25-/m0/s1

InChI Key

TWDCYBTXSUNASK-WGGIPMEBSA-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 benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzophenones

Direct Parent

Benzophenones

Alternative Parents

Substituents

Benzophenone
O-glucuronide
1-o-glucuronide
Aryl-phenylketone
Diphenylmethane
Glucuronic acid or derivatives
Hexose monosaccharide
Benzoyl
Aryl ketone
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Pyran
Oxane
Hydroxy acid
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Acetal
Carboxylic acid derivative
Polyol
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.53	ALOGPS
logP	1.26	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.28	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	116.93 m³·mol⁻¹	ChemAxon
Polarizability	51.3 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

HMDB0010334

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB027486

KNApSAcK ID

Not Available

Chemspider ID

116053

KEGG Compound ID

Not Available

BioCyc ID

Beta-D-Glucuronides

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131281

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3,17-Androstanediol glucuronide (NP0090877)

MOL for NP0090877 (3,17-Androstanediol glucuronide)

3D MOL for NP0090877 (3,17-Androstanediol glucuronide)

3D SDF for NP0090877 (3,17-Androstanediol glucuronide)

3D-SDF for NP0090877 (3,17-Androstanediol glucuronide)

PDB for NP0090877 (3,17-Androstanediol glucuronide)

3D PDB for NP0090877 (3,17-Androstanediol glucuronide)

SMILES for NP0090877 (3,17-Androstanediol glucuronide)

INCHI for NP0090877 (3,17-Androstanediol glucuronide)

Structure for NP0090877 (3,17-Androstanediol glucuronide)

3D Structure for NP0090877 (3,17-Androstanediol glucuronide)