Showing Compound Tetrahydroaldosterone-3-glucuronide (FDB027509)

Record Information

Version

1.0

Creation date

2011-09-21 01:25:32 UTC

Update date

2015-07-21 06:59:08 UTC

Primary ID

FDB027509

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Tetrahydroaldosterone-3-glucuronide

Description

Tetrahydroaldosterone-3-glucuronide is a natural human metabolite of Tetrahydroaldosterone generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. [HMDB]

CAS Number

20605-81-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(3alpha,5beta,11beta)-11,18-Epoxy-18,21-dihydro-20-oxopregnan-3-yl-beta-D-glucopyranosiduronic acid	HMDB
(3alpha,5beta,11beta)-11,18-epoxy-18,21-dihydro-20-oxopregnan-3-yl-beta-D-Glucopyranosiduronic acid	hmdb
(3alpha,5beta,11beta)-11,18-Epoxy-18,21-dihydro-20-oxopregnan-3-yl-beta-delta-glucopyranosiduronic acid	HMDB
(3alpha,5beta,11beta)-11,18-epoxy-18,21-dihydro-20-oxopregnan-3-yl-beta-delta-Glucopyranosiduronic acid	hmdb
11 beta,18-Epoxy-18,21-dihydroxy-20-oxo-5 beta-pregnan-3 alpha-yl beta-D-glucopyranosiduronic acid	MeSH
11beta,18-Epoxy-18,21-dihydroxy-20-oxo-5beta-pregnan-3alpha-yl beta-D-glucopyranosiduronic acid	HMDB
11beta,18-Epoxy-18,21-dihydroxy-20-oxo-5beta-pregnan-3alpha-yl beta-delta-glucopyranosiduronic acid	HMDB
TA-ga	MeSH
Tetrahydroaldosterone 3 beta-glucosiduronic acid	MeSH
tetrahydroaldosterone 3 beta-glucosiduronic acid	hmdb

Showing 1 to 10 of 11 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.49 g/L	ALOGPS
logP	-0.06	ALOGPS
logP	-0.073	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	183.21 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.78 m³·mol⁻¹	ChemAxon
Polarizability	56.19 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C27H40O11

IUPAC name

(2S,3S,4R,5R,6R)-3,4,5-trihydroxy-6-{[(2S,14S,16S)-18-hydroxy-2-(2-hydroxyacetyl)-14-methyl-17-oxapentacyclo[14.2.1.0¹,⁵.0⁶,¹⁵.0⁹,¹⁴]nonadecan-11-yl]oxy}oxane-2-carboxylic acid

InChI Identifier

InChI=1S/C27H40O11/c1-26-7-6-12(36-24-21(32)19(30)20(31)22(38-24)23(33)34)8-11(26)2-3-13-14-4-5-15(16(29)10-28)27(14)9-17(18(13)26)37-25(27)35/h11-15,17-22,24-25,28,30-32,35H,2-10H2,1H3,(H,33,34)/t11?,12?,13?,14?,15-,17+,18?,19-,20+,21-,22+,24-,25?,26+,27?/m1/s1

InChI Key

CGIURIOFMWUPSV-RUQPETGGSA-N

Isomeric SMILES

[H][C@@]12CC3(C(O)O1)C(CC[C@@H]3C(=O)CO)C1CCC3CC(CC[C@]3(C)C21)O[C@@H]1O[C@@H]([C@@H](O)[C@@H](O)[C@H]1O)C(O)=O

Average Molecular Weight

540.5999

Monoisotopic Molecular Weight

540.257062122

Classification

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
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Oxepane
Pyran
Oxane
Hydroxy acid
Monosaccharide
Alpha-hydroxy ketone
Tetrahydrofuran
Secondary alcohol
Hemiacetal
Ketone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Acetal
Polyol
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Organ and components:

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Molecular messenger:

Signaling molecule

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0ab9-6103690000-14047f2bdb0ef3dd341e	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01b9-6100219000-9d173de05066ac0a8d12	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tetrahydroaldosterone-3-glucuronide, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01bd-0009160000-22ec70399a690aea5bda	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0109000000-e0d766932d3840e4913d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pvi-0229000000-c69b52480d42244e92a0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01pa-2208490000-09855d6e39bfbeb9aa78	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dj-2109210000-4ded13a1278e25bc2630	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08fr-4109000000-dfd16e49a098227e09d3	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000090000-39e628b55b951b77518f	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000b-0249130000-ba4c979ef6f5eec9393d	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-1916070000-9ed3e990712d132a8009	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000390000-33110ebe67045c65c29a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9101420000-e3cc0020a34c77863fcb	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4r-9003610000-08c23161a8e55aa0a0b7	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

146888

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

167918

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB10357

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Beta-glucuronidase	GUSB	P08236
UDP-glucuronosyltransferase 1-1	UGT1A1	P22309
UDP-glucuronosyltransferase 1-3	UGT1A3	P35503
UDP-glucuronosyltransferase 1-4	UGT1A4	P22310
UDP-glucuronosyltransferase 1-5	UGT1A5	P35504
UDP-glucuronosyltransferase 1-6	UGT1A6	P19224
UDP-glucuronosyltransferase 1-9	UGT1A9	O60656
UDP-glucuronosyltransferase 2A1	UGT2A1	Q9Y4X1
UDP-glucuronosyltransferase 2A3	UGT2A3	Q6UWM9
UDP-glucuronosyltransferase 2B11	UGT2B11	O75310