NP-MRD: Showing NP-Card for Androsterone glucuronide (NP0087012)

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Record Information

Version

2.0

Created at

2022-05-11 16:37:20 UTC

Updated at

2022-05-11 16:37:20 UTC

NP-MRD ID

NP0087012

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Androsterone glucuronide

Description

Androsterone glucuronide, also known as etiocholanolone 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, androsterone glucuronide is considered to be a steroid conjugate lipid molecule. Androsterone glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Androsterone glucuronide and uridine 5'-diphosphate can be biosynthesized from androsterone and uridine diphosphate glucuronic acid through its interaction with the enzyme UDP-glucuronosyltransferase 1-1. In humans, androsterone glucuronide is involved in androstenedione metabolism. Androsterone glucuronide was first documented in 1996 (PMID: 8837296). A steroid glucosiduronic acid having androsterone as the steroid component (PMID: 9141545) (PMID: 12051338).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Untitled Document-2
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Untitled Document-2
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 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 16  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 18  1  0  0  0  0
  6 24  1  1  0  0  0
  4 25  1  1  0  0  0
  2 26  1  1  0  0  0
 11 27  1  1  0  0  0
 15 28  1  1  0  0  0
 18 29  1  1  0  0  0
  1 30  1  6  0  0  0
  3 31  1  6  0  0  0
  8 25  1  6  0  0  0
 10 32  1  6  0  0  0
 16 33  1  6  0  0  0
 17 34  1  6  0  0  0
 23 35  2  0  0  0  0
 24 36  2  0  0  0  0
 24 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087012

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,18-,19-,20+,21-,23+,24-,25-/m0/s1

> <INCHI_KEY>
VFUIRAVTUVCQTF-BSOWLZGZSA-N

> <FORMULA>
C25H38O8

> <MOLECULAR_WEIGHT>
466.5644

> <EXACT_MASS>
466.256668192

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
50.56350254454351

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
2.3167234289999996

> <ALOGPS_LOGS>
-3.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.227618824082947

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4672441884156613

> <JCHEM_PKA_STRONGEST_BASIC>
-3.68649922655017

> <JCHEM_POLAR_SURFACE_AREA>
133.51999999999998

> <JCHEM_REFRACTIVITY>
116.08959999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
etiocholanolone glucuronide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Untitled Document-2                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.520  -0.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.520  -1.740   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.186  -2.510   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.852  -1.740   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.852  -0.200   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.186   0.570   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.185  -0.200   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.185  -1.740   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.149  -2.510   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.483  -1.740   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.483  -0.200   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.149   0.570   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.816  -2.510   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.150  -1.740   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.150  -0.200   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.816   0.570   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.484   0.570   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.484   2.110   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.150   2.880   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.816   2.110   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.948   0.094   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.853   1.340   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.948   2.586   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.186   2.110   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.519  -2.510   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -7.853  -2.510   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.483   1.340   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0       4.150   1.340   0.000  0.00  0.00           H+0
HETATM   29  C   UNK     0       5.644   3.641   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -7.853   0.570   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -5.186  -4.050   0.000  0.00  0.00           O+0
HETATM   32  H   UNK     0       1.483  -3.280   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.816  -0.970   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.484  -0.970   0.000  0.00  0.00           H+0
HETATM   35  O   UNK     0       7.424   4.050   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -3.852   2.880   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -6.520   2.880   0.000  0.00  0.00           O+0
CONECT    1    2    6   30                                                  
CONECT    2    1    3   26                                                  
CONECT    3    2    4   31                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1   24                                                  
CONECT    7    8   12                                                       
CONECT    8    7    9   25                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13   32                                             
CONECT   11   10   12   16   27                                             
CONECT   12   11    7                                                       
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   28                                             
CONECT   16   15   11   20   33                                             
CONECT   17   15   18   21   34                                             
CONECT   18   17   19   23   29                                             
CONECT   19   18   20                                                       
CONECT   20   19   16                                                       
CONECT   21   17   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18   35                                                  
CONECT   24    6   36   37                                                  
CONECT   25    4    8                                                       
CONECT   26    2                                                            
CONECT   27   11                                                            
CONECT   28   15                                                            
CONECT   29   18                                                            
CONECT   30    1                                                            
CONECT   31    3                                                            
CONECT   32   10                                                            
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   23                                                            
CONECT   36   24                                                            
CONECT   37   24                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
3alpha-Hydroxy-5alpha-androstan-17-one glucuronide	ChEBI
Androsterone 3-glucuronide	ChEBI
Androsterone glucosiduronate	ChEBI
Androsterone glucuronoside	ChEBI
Etiocholanolone glucuronide	ChEBI
3a-Hydroxy-5a-androstan-17-one glucuronide	Generator
3Α-hydroxy-5α-androstan-17-one glucuronide	Generator
Androsterone glucosiduronic acid	Generator
5a-Androstan-3a-ol-17-one glucuronide	HMDB
Androsterone monoglucosiduronate	HMDB
b-D-17-oxo-5a-Androstan-3a-yl glucopyranosiduronic acid	HMDB
Androsterone glucuronide, sodium salt, (3alpha,5alpha)-isomer	HMDB
Androsterone glucuronide, sodium salt, (3alpha,5beta)-isomer	HMDB
Androsterone glucuronide, (beta-D)-isomer	HMDB
Androsterone glucuronide, (3beta,5alpha)-isomer	HMDB
(3alpha,5alpha)-17-Oxoandrostan-3-yl beta-D-glucopyranosiduronic acid	HMDB

Chemical Formula

C₂₅H₃₈O₈

Average Mass

466.5644 Da

Monoisotopic Mass

466.25667 Da

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

etiocholanolone glucuronide

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,18-,19-,20+,21-,23+,24-,25-/m0/s1

InChI Key

VFUIRAVTUVCQTF-BSOWLZGZSA-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 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
Androstane-skeleton
Oxosteroid
17-oxosteroid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Monosaccharide
Pyran
Oxane
Hydroxy acid
Ketone
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

beta-D-glucosiduronic acid (CHEBI:28832 )
steroid glucosiduronic acid (CHEBI:28832 )
C19 steroids (androgens) and derivatives (C11135 )
Glucuronides (C11135 )
Glucuronides (LMST05010013 )

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	2.06	ALOGPS
logP	2.32	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.47	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	116.09 m³·mol⁻¹	ChemAxon
Polarizability	50.56 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

HMDB0002829

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023070

KNApSAcK ID

Not Available

Chemspider ID

102793

KEGG Compound ID

C11135

BioCyc ID

Not Available

BiGG ID

2304839

Wikipedia Link

Androsterone glucuronide

METLIN ID

2796

PubChem Compound

114833

PDB ID

Not Available

ChEBI ID

28832

Good Scents ID

Not Available

References

General References

Tchernof A, Labrie F, Belanger A, Prud'homme D, Bouchard C, Tremblay A, Nadeau A, Despres JP: Androstane-3alpha,17beta-diol glucuronide as a steroid correlate of visceral obesity in men. J Clin Endocrinol Metab. 1997 May;82(5):1528-34. doi: 10.1210/jcem.82.5.3924. [PubMed:9141545 ]
Nakazono T, Kashimura S, Hayashiba Y, Hisatomi T, Hara K: Identification of human urine stains by HPLC analysis of 17-ketosteroid conjugates. J Forensic Sci. 2002 May;47(3):568-72. [PubMed:12051338 ]
Brind J, Borofsky N, Chervinsky K, Vogelman JH, Orentreich N: A simple, differential extraction method for the simultaneous direct radioimmunoassay of androgens and androgen glucuronides in human serum. Steroids. 1996 Jul;61(7):429-32. doi: 10.1016/0039-128x(96)00063-3. [PubMed:8837296 ]

Showing NP-Card for Androsterone glucuronide (NP0087012)

MOL for NP0087012 (Androsterone glucuronide)

3D MOL for NP0087012 (Androsterone glucuronide)

3D SDF for NP0087012 (Androsterone glucuronide)

3D-SDF for NP0087012 (Androsterone glucuronide)

PDB for NP0087012 (Androsterone glucuronide)

3D PDB for NP0087012 (Androsterone glucuronide)

SMILES for NP0087012 (Androsterone glucuronide)

INCHI for NP0087012 (Androsterone glucuronide)

Structure for NP0087012 (Androsterone glucuronide)

3D Structure for NP0087012 (Androsterone glucuronide)