Bovine Metabolome Database: Showing metabocard for Taurodeoxycholic acid (BMDB0000896)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:38:14 UTC

Update Date

2020-05-11 20:09:24 UTC

BMDB ID

BMDB0000896

Secondary Accession Numbers

BMDB00896

Metabolite Identification

Common Name

Taurodeoxycholic acid

Description

Taurodeoxycholic acid, also known as taurodeoxycholate or acid, taurodeoxycholic, belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety. Based on a literature review a significant number of articles have been published on Taurodeoxycholic acid.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Taurodeoxycholate	ChEBI
Acid, taurodeoxycholic	HMDB
Deoxycholate, taurine	HMDB
Sodium taurodeoxycholate	HMDB
Taurine deoxycholate	HMDB
Deoxycholyltaurine	HMDB
Taurodeoxycholate, sodium	HMDB
Deoxytaurocholate	HMDB
Deoxytaurocholic acid	HMDB
N-(3a,12a-Dihydroxy-5b-cholan-24-oyl)-taurine	HMDB
Sodium taurodeoxylate	HMDB
Taurodeoxycholic acid sodium salt	HMDB
Taurodeoxycholic acid sodium salt hydrate	HMDB
Taurodesoxycholate	HMDB
Taurodesoxycholic acid	HMDB
Tudcabil	HMDB

Chemical Formula

C₂₆H₄₅NO₆S

Average Molecular Weight

499.704

Monoisotopic Molecular Weight

499.296758867

IUPAC Name

2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethane-1-sulfonic acid

Traditional Name

2-[(4R)-4-[(1S,2S,5R,7R,10R,11S,14R,15R,16S)-5,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanamido]ethanesulfonic acid

CAS Registry Number

516-50-7

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@H](O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(=O)NCCS(O)(=O)=O

InChI Identifier

InChI=1S/C26H45NO6S/c1-16(4-9-24(30)27-12-13-34(31,32)33)20-7-8-21-19-6-5-17-14-18(28)10-11-25(17,2)22(19)15-23(29)26(20,21)3/h16-23,28-29H,4-15H2,1-3H3,(H,27,30)(H,31,32,33)/t16-,17-,18-,19+,20-,21+,22+,23+,25+,26-/m1/s1

InChI Key

AWDRATDZQPNJFN-VAYUFCLWSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as taurinated bile acids and derivatives. These are bile acid derivatives containing a taurine conjugated to the bile acid moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Taurinated bile acids and derivatives

Alternative Parents

Substituents

Taurinated bile acid
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
3-hydroxysteroid
12-hydroxysteroid
3-alpha-hydroxysteroid
Hydroxysteroid
Fatty amide
Fatty acyl
N-acyl-amine
Cyclic alcohol
Alkanesulfonic acid
Sulfonyl
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Organosulfonic acid
Secondary alcohol
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

bile acid taurine conjugate (CHEBI:9410 )
Taurine conjugates (LMST05040013 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	204 - 208 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	41 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.19	ALOGPS
logP	1.14	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	-0.75	ChemAxon
pKa (Strongest Basic)	-0.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	123.93 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	130.6 m³·mol⁻¹	ChemAxon
Polarizability	56.55 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lu-0111900000-a90e31e3c4cf2f0c6f3a	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-004i-4201229000-01b8d5e2d286a6e403aa	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0ikd-0047930000-8f9f65d8c1d3c8253501	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03g0-0950300000-d3a559bd8c5ccd049d7b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9545740000-d9a7750b1b579bd2bb05	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0a4i-0009500000-11f56619a58a7f9fe2df	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000690000-02978b9c502ebd7d68d6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000900000-c7214ee029f71204bb8f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0470-1596200000-357f5937f8ae2d422ba2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0470-1596200000-078d7c7763da8bb11d2e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01si-0302920000-c2629184642c876303ac	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-1904400000-52b97ee82fecb26d2df7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004l-8906300000-1c0dd8ea92d737243ce2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000t-2001900000-5090bd6cae3b061c80e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-7504900000-0d93eba8b9f15618357f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001l-9202000000-2e68ed7e43eb97ec4ad8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000900000-31f17d1d48b7afdf3bae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0000900000-09a127bb8eacbd0a6ab7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001j-9201800000-97168e49aaa085a3735c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-0000950000-e77d9cab9a8afc22e8b1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08gi-2414910000-42610292496f161b3e8d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052e-8912000000-fd93247f3ff2a43d83dd	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm

Biospecimen Locations

Blood
Intestine
Liver

Pathways

Name	SMPDB/Pathwhiz	KEGG
Bile Acid Biosynthesis		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Abnormal (male calves/vaccination biomarker)	PMID: 25828073	details

External Links

HMDB ID

HMDB0000896

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022304

KNApSAcK ID

Not Available

Chemspider ID

2015539

KEGG Compound ID

C05463

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Taurodeoxycholic_acid

METLIN ID

5853

PubChem Compound

2733768

PDB ID

Not Available

ChEBI ID

9410

References

Synthesis Reference

Parenti, Massimo. Preparation of tauroursodesoxycholic acid dihydrate. Eur. Pat. Appl. (1990), 3 pp. CODEN: EPXXDW EP 400695 A2 19901205 CAN 114:82269 AN 1991:82269

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Taurodeoxycholic acid (BMDB0000896)

Structure for BMDB0000896 (Taurodeoxycholic acid)