Showing Compound Lithocholate 3-O-glucuronide (FDB023020)

Record Information

Version

1.0

Creation date

2011-09-21 00:23:22 UTC

Update date

2015-07-21 06:57:29 UTC

Primary ID

FDB023020

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Lithocholate 3-O-glucuronide

Description

Analysis of sequential bile samples by thin-layer chromatography (TLC) demonstrated that lithocholic acid glucuronide was present in bile throughout the course of the experiments and that its secretion rate paralleled that of total isotope secretion. Initial confirmation of the identity of this metabolite was obtained by the recovery of labeled lithocholic acid after beta-glucuronidase hydrolysis of bile samples. Glucuronates; Lithocholic Acid [HMDB]

CAS Number

75239-91-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Showing 1 to 4 of 4 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	2.72	ALOGPS
logP	3.57	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	139.96 m³·mol⁻¹	ChemAxon
Polarizability	61.69 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C30H48O9

IUPAC name

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

InChI Identifier

InChI=1S/C30H48O9/c1-15(4-9-22(31)32)19-7-8-20-18-6-5-16-14-17(10-12-29(16,2)21(18)11-13-30(19,20)3)38-28-25(35)23(33)24(34)26(39-28)27(36)37/h15-21,23-26,28,33-35H,4-14H2,1-3H3,(H,31,32)(H,36,37)/t15-,16-,17+,18+,19-,20+,21+,23+,24+,25-,26+,28-,29+,30-/m1/s1

InChI Key

GIQXKAXWRLHLDD-VOJQCDQYSA-N

Isomeric SMILES

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

Average Molecular Weight

552.6967

Monoisotopic Molecular Weight

552.329833134

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
Bile acid, alcohol, or derivatives
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Pyran
Hydroxy acid
Oxane
Monosaccharide
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen 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

Subcellular:

Biofluid and excreta:

Organ and components:

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

Show entries

Search:

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	Lithocholate 3-O-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-002r-6205590000-38694c7925c18dd4ba1c	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-3406029000-7229a6fee33463889575	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, "Lithocholate 3-O-glucuronide,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_3_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_3_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lithocholate 3-O-glucuronide, TMS_3_8, 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	splash10-0pdr-0009060000-fa8d533035a152914053	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0009010000-74247478eda83981ec00	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-016r-0219000000-be750b2c39743b6aa36b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zi0-1206190000-7574484741f16ee01e6a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-2209120000-c6eb5b3f627f13090a9e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-6109000000-d30e9d34ffefc8d871e6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000090000-f7afaa19600b0cf8248c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ue9-3101290000-0da9a01a36fd677f1f7f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9103420000-b66fce6cf25d53f02e6f	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-0000190000-b0bd8da6810e3293385c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-2296230000-2b21fbe8cdc2bfaee104	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-2934200000-59a123ab0679c6c41b9d	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

112415

ChEMBL ID

Not Available

KEGG Compound ID

C03033

Pubchem Compound ID

126511

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02513

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

Show entries

Search:

Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Show entries

Search:

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