NP-MRD: Showing NP-Card for Testosterone glucuronide (NP0087034)

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Record Information

Version

2.0

Created at

2022-05-11 16:38:00 UTC

Updated at

2022-05-11 16:38:00 UTC

NP-MRD ID

NP0087034

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Testosterone glucuronide

Description

Testosterone 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, testosterone glucuronide is considered to be a steroid conjugate lipid molecule. A steroid glucosiduronic that is testosterone carrying a glucosiduronic acid residue at position 17. Testosterone glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Testosterone glucuronide can be biosynthesized from testosterone; which is catalyzed by the enzyme UDP-glucuronosyltransferase 2B17. Testosterone glucuronide is found in Homo sapiens. Testosterone glucuronide was first documented in 1987 (PMID: 3560942). In humans, testosterone glucuronide is involved in androgen and estrogen metabolism (PMID: 10732948) (PMID: 16470578) (PMID: 2030059) (PMID: 8327267).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219392D          

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 23 25  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 31  1  0  0  0  0
 29 32  1  0  0  0  0
 31 33  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0087034

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O8/c1-24-9-7-13(26)11-12(24)3-4-14-15-5-6-17(25(15,2)10-8-16(14)24)32-23-20(29)18(27)19(28)21(33-23)22(30)31/h11,14-21,23,27-29H,3-10H2,1-2H3,(H,30,31)/t14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1

> <INCHI_KEY>
NIKZPECGCSUSBV-HMAFJQTKSA-N

> <FORMULA>
C25H36O8

> <MOLECULAR_WEIGHT>
464.5485

> <EXACT_MASS>
464.241018128

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
49.28932022433058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
1.9148621899999991

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.227590377074694

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.627460376614403

> <JCHEM_PKA_STRONGEST_BASIC>
-3.686499496639537

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
116.71049999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
testosterone glucuronide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      50.098 -26.176   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      52.282 -28.427   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      55.169 -27.834   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      56.126 -24.906   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      53.040 -21.467   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      52.083 -24.395   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      55.576 -22.296   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      39.857 -32.810   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      48.163 -26.569   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      44.106 -28.890   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      48.163 -28.109   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      44.094 -30.430   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      51.605 -25.859   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      52.633 -27.005   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      54.140 -26.687   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      54.619 -25.224   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      49.620 -27.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      48.163 -29.649   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      45.495 -29.649   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      46.829 -30.420   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      53.590 -24.077   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      46.829 -27.339   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      50.519 -28.879   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      45.495 -28.109   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      49.620 -30.119   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      42.666 -29.561   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      46.854 -32.023   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      41.207 -30.374   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      45.471 -32.836   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      54.069 -22.614   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      41.194 -32.045   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      44.081 -32.034   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      42.641 -32.881   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0      48.924 -30.874   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      46.562 -29.033   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      47.732 -31.280   0.000  0.00  0.00           H+0
CONECT    1   13   17                                                       
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   16                                                            
CONECT    5   30                                                            
CONECT    6   13   21                                                       
CONECT    7   30                                                            
CONECT    8   31                                                            
CONECT    9   11                                                            
CONECT   10   12                                                            
CONECT   11    9   17   18   22                                             
CONECT   12   10   19   26   32                                             
CONECT   13    1    6   14                                                  
CONECT   14    2   13   15                                                  
CONECT   15    3   14   16                                                  
CONECT   16    4   15   21                                                  
CONECT   17    1   11   23                                                  
CONECT   18   11   20   25   34                                             
CONECT   19   12   20   24   35                                             
CONECT   20   18   19   27   36                                             
CONECT   21    6   16   30                                                  
CONECT   22   11   24                                                       
CONECT   23   17   25                                                       
CONECT   24   19   22                                                       
CONECT   25   18   23                                                       
CONECT   26   12   28                                                       
CONECT   27   20   29                                                       
CONECT   28   26   31                                                       
CONECT   29   27   32                                                       
CONECT   30    5    7   21                                                  
CONECT   31    8   28   33                                                  
CONECT   32   12   29   33                                                  
CONECT   33   31   32                                                       
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
Testosterone 17beta-(beta-D-glucuronide)	ChEBI
Testosterone glucuronoside	ChEBI
Testosterone 17b-(b-D-glucuronide)	Generator
Testosterone 17β-(β-D-glucuronide)	Generator
(17b)-3-Oxoandrost-4-en-17-yl b-D-glucopyranosiduronic acid	HMDB
b-D-3-Oxoandrost-4-en-17b-yl glucopyranosiduronic acid	HMDB
b-D-Androstane glucopyranosiduronic acid	HMDB
Epitestosterone glucuronide	HMDB
Testosterone 17-glucosiduronate	HMDB
Testosterone 17-glucuronide	HMDB
Testosterone glucopyranuronoside	HMDB
Testosterone glucosiduronide	HMDB
Testosterone glucuronate	HMDB
Testosterone-glucuronide	HMDB
(alpha)-Isomer OF testosterone glucuronate	HMDB

Chemical Formula

C₂₅H₃₆O₈

Average Mass

464.5485 Da

Monoisotopic Mass

464.24102 Da

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

testosterone glucuronide

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@H](O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

InChI Identifier

InChI=1S/C25H36O8/c1-24-9-7-13(26)11-12(24)3-4-14-15-5-6-17(25(15,2)10-8-16(14)24)32-23-20(29)18(27)19(28)21(33-23)22(30)31/h11,14-21,23,27-29H,3-10H2,1-2H3,(H,30,31)/t14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1

InChI Key

NIKZPECGCSUSBV-HMAFJQTKSA-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
Homo sapiens	LOTUS Database	35616633
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
Androgen-skeleton
Androstane-skeleton
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
Delta-4-steroid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Cyclohexenone
Beta-hydroxy acid
Monosaccharide
Hydroxy acid
Pyran
Oxane
Cyclic ketone
Secondary alcohol
Ketone
Polyol
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

steroid glucosiduronic acid (CHEBI:28835 )
C19 steroids (androgens) and derivatives (C11134 )
Glucuronides (C11134 )
Glucuronides (LMST05010012 )

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	1.83	ALOGPS
logP	1.91	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	116.71 m³·mol⁻¹	ChemAxon
Polarizability	49.29 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

HMDB0003193

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023122

KNApSAcK ID

Not Available

Chemspider ID

97270

KEGG Compound ID

C11134

BioCyc ID

Not Available

BiGG ID

2304840

Wikipedia Link

Testosterone glucuronide

METLIN ID

2794

PubChem Compound

108192

PDB ID

Not Available

ChEBI ID

28835

Good Scents ID

Not Available

References

General References

van de Kerkhof DH, de Boer D, Thijssen JH, Maes RA: Evaluation of testosterone/epitestosterone ratio influential factors as determined in doping analysis. J Anal Toxicol. 2000 Mar;24(2):102-15. doi: 10.1093/jat/24.2.102. [PubMed:10732948 ]
Perera DM, McGarrigle HH, Lawrence DM, Lucas M: Amniotic fluid testosterone and testosterone glucuronide levels in the determination of foetal sex. J Steroid Biochem. 1987 Feb;26(2):273-7. doi: 10.1016/0022-4731(87)90082-3. [PubMed:3560942 ]
Jimenez C, de la Torre R, Segura J, Ventura R: Stability studies of testosterone and epitestosterone glucuronides in urine. Rapid Commun Mass Spectrom. 2006;20(5):858-64. doi: 10.1002/rcm.2387. [PubMed:16470578 ]
de Boer D, de Jong EG, van Rossum JM, Maes RA: Doping control of testosterone and human chorionic gonadotrophin: a case study. Int J Sports Med. 1991 Feb;12(1):46-51. doi: 10.1055/s-2007-1024654. [PubMed:2030059 ]
Raynaud E, Audran M, Pages JC, Brun JF, Fedou C, Chanal JL, Orsetti A: [Study of urinary excretion of testosterone and epitestosterone glucuronides in children and adolescents]. Pathol Biol (Paris). 1993 Feb;41(2):159-63. [PubMed:8327267 ]

Showing NP-Card for Testosterone glucuronide (NP0087034)

MOL for NP0087034 (Testosterone glucuronide)

3D MOL for NP0087034 (Testosterone glucuronide)

3D SDF for NP0087034 (Testosterone glucuronide)

3D-SDF for NP0087034 (Testosterone glucuronide)

PDB for NP0087034 (Testosterone glucuronide)

3D PDB for NP0087034 (Testosterone glucuronide)

SMILES for NP0087034 (Testosterone glucuronide)

INCHI for NP0087034 (Testosterone glucuronide)

Structure for NP0087034 (Testosterone glucuronide)

3D Structure for NP0087034 (Testosterone glucuronide)