NP-MRD: Showing NP-Card for Etiocholanolone glucuronide (NP0087181)

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Record Information

Version

2.0

Created at

2022-05-11 16:42:22 UTC

Updated at

2022-05-11 16:42:23 UTC

NP-MRD ID

NP0087181

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Etiocholanolone glucuronide

Description

Etiocholanolone glucuronide, also known as androsterone glucosiduronate, 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, etiocholanolone glucuronide is considered to be a steroid conjugate lipid molecule. Etiocholanolone glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. ETIO-G has much higher water solubility than etiocholanolone and is eventually excreted in the urine via the kidneys. Etiocholanolone glucuronide and uridine 5'-diphosphate can be biosynthesized from etiocholanolone and uridine diphosphate glucuronic acid; which is mediated by the enzyme UDP-glucuronosyltransferase 1-1. In humans, etiocholanolone glucuronide is involved in androstenedione metabolism. Etiocholanolone glucuronide (ETIO-G) is an endogenous, naturally occurring metabolite of testosterone. Along with androsterone glucuronide, it is one of the major inactive metabolites of testosterone. Etiocholanolone glucuronide is found in Apis cerana. Etiocholanolone glucuronide was first documented in 2002 (PMID: 12051338). It is formed in the liver from etiocholanolone by UDP-glucuronyltransferases.

Structure

MOL 3D MOL SDF PDB SMILES InChI

HMDB04484.mol
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HMDB04484.mol
  Mrv0541 02231219562D          

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 10  5  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 10  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 12  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 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
 23 24  1  1  0  0  0
 19 25  1  1  0  0  0
 21 26  1  1  0  0  0
  4 27  1  1  0  0  0
  5 28  1  1  0  0  0
  9 29  1  1  0  0  0
 12 30  1  1  0  0  0
 17 31  2  0  0  0  0
 24 32  2  0  0  0  0
 24 33  1  0  0  0  0
 18 34  1  6  0  0  0
 20 35  1  6  0  0  0
  2 26  1  6  0  0  0
 10 36  1  6  0  0  0
 11 37  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0087181

> <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+/m1/s1

> <INCHI_KEY>
VFUIRAVTUVCQTF-SDHZCXLISA-N

> <FORMULA>
C25H38O8

> <MOLECULAR_WEIGHT>
466.5644

> <EXACT_MASS>
466.256668192

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
50.36999411721337

> <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,7R,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>
133.52

> <JCHEM_REFRACTIVITY>
116.08959999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
androsterone glucuronide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HMDB04484.mol                                     
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.185  -0.200   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.185  -1.740   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.149  -2.510   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.483  -1.740   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.483  -0.200   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.149   0.570   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.816  -2.510   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.150  -1.740   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.150  -0.200   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.816   0.570   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.484   0.570   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.484   2.110   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.150   2.880   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.816   2.110   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.948   0.094   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.853   1.340   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.948   2.586   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.520  -0.201   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.519  -1.741   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.185  -2.510   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.852  -1.740   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -3.851  -0.202   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -5.186   0.570   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      -7.853  -2.511   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.519  -2.510   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       1.483  -3.280   0.000  0.00  0.00           H+0
HETATM   28  C   UNK     0       1.483   1.340   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0       4.150   1.340   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0       5.645   3.641   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       7.424   4.050   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -3.853   2.880   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -6.520   2.880   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -7.853   0.569   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -5.185  -4.050   0.000  0.00  0.00           O+0
HETATM   36  H   UNK     0       2.816  -0.970   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       5.484  -0.970   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   27                                             
CONECT    5    4    6   10   28                                             
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   29                                             
CONECT   10    9    5   14   36                                             
CONECT   11    9   12   15   37                                             
CONECT   12   11   13   17   30                                             
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   31                                                  
CONECT   18   19   23   34                                                  
CONECT   19   18   20   25                                                  
CONECT   20   19   21   35                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23   32   33                                                  
CONECT   25   19                                                            
CONECT   26   21    2                                                       
CONECT   27    4                                                            
CONECT   28    5                                                            
CONECT   29    9                                                            
CONECT   30   12                                                            
CONECT   31   17                                                            
CONECT   32   24                                                            
CONECT   33   24                                                            
CONECT   34   18                                                            
CONECT   35   20                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
3alpha-Hydroxyetiocholan-17-one 3-glucosiduronic acid	ChEBI
3alpha-Hydroxyetiocholan-17-one 3-glucuronide	ChEBI
Etiocholan-3alpha-ol-17-one 3-glucuronide	ChEBI
Etiocholan-3alpha-ol-17-one 3-glucuronoside	ChEBI
3a-Hydroxyetiocholan-17-one 3-glucosiduronate	Generator
3a-Hydroxyetiocholan-17-one 3-glucosiduronic acid	Generator
3alpha-Hydroxyetiocholan-17-one 3-glucosiduronate	Generator
3Α-hydroxyetiocholan-17-one 3-glucosiduronate	Generator
3Α-hydroxyetiocholan-17-one 3-glucosiduronic acid	Generator
3a-Hydroxyetiocholan-17-one 3-glucuronide	Generator
3Α-hydroxyetiocholan-17-one 3-glucuronide	Generator
Etiocholan-3a-ol-17-one 3-glucuronide	Generator
Etiocholan-3α-ol-17-one 3-glucuronide	Generator
Etiocholan-3a-ol-17-one 3-glucuronoside	Generator
Etiocholan-3α-ol-17-one 3-glucuronoside	Generator
17-Oxoandrostan-3-yl hexopyranosiduronic acid	HMDB
3alpha-Hydroxy-5beta-androstan-17-one 3-glucuronide	HMDB
5Alpha.-androstan-3.alpha.-ol-17-one glucoronide	HMDB
5beta-Androstan-3alpha-ol-17-one 3-glucuronide	HMDB
Etiocholanolone 3-glucuronide	HMDB
Androsterone glucosiduronate	HMDB
Androsterone glucuronide	HMDB
Androsterone glucuronide, (3beta,5alpha)-isomer	HMDB
Androsterone glucuronide, (beta-D)-isomer	HMDB
Androsterone glucuronide, sodium salt, (3alpha,5alpha)-isomer	HMDB
Androsterone glucuronide, sodium salt, (3alpha,5beta)-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,7R,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

androsterone 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+/m1/s1

InChI Key

VFUIRAVTUVCQTF-SDHZCXLISA-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
Apis cerana	LOTUS Database	35616633
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

steroid glucosiduronic acid (CHEBI:37451 )
Glucuronides (C11136 )
Glucuronides (LMST05010014 )

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	50.37 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

HMDB0004484

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023376

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Etiocholanolone glucuronide

METLIN ID

7064

PubChem Compound

443078

PDB ID

Not Available

ChEBI ID

37451

Good Scents ID

Not Available

References

General References

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 ]

Showing NP-Card for Etiocholanolone glucuronide (NP0087181)

MOL for NP0087181 (Etiocholanolone glucuronide)

3D MOL for NP0087181 (Etiocholanolone glucuronide)

3D SDF for NP0087181 (Etiocholanolone glucuronide)

3D-SDF for NP0087181 (Etiocholanolone glucuronide)

PDB for NP0087181 (Etiocholanolone glucuronide)

3D PDB for NP0087181 (Etiocholanolone glucuronide)

SMILES for NP0087181 (Etiocholanolone glucuronide)

INCHI for NP0087181 (Etiocholanolone glucuronide)

Structure for NP0087181 (Etiocholanolone glucuronide)

3D Structure for NP0087181 (Etiocholanolone glucuronide)