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Record Information
Version5.0
StatusPredicted
Creation Date2021-08-30 18:38:56 UTC
Update Date2022-11-15 17:47:02 UTC
HMDB IDHMDB0242401
Secondary Accession NumbersNone
Metabolite Identification
Common NameChenodeoxycholylvaline
DescriptionChenodeoxycholylvaline belongs to a class of molecules known as bile acid-amino acid conjugates. These are bile acid conjugates that consist of a primary bile acid such as cholic acid, doxycholic acid and chenodeoxycholic acid, conjugated to an amino acid. Chenodeoxycholylvaline consists of the bile acid chenodeoxycholic acid conjugated to the amino acid Valine conjugated at the C24 acyl site.Bile acids play an important role in regulating various physiological systems, such as fat digestion, cholesterol metabolism, vitamin absorption, liver function, and enterohepatic circulation through their combined signaling, detergent, and antimicrobial mechanisms (PMID: 34127070 ). Bile acids also act as detergents in the gut and support the absorption of fats through the intestinal membrane. These same properties allow for the disruption of bacterial membranes, thereby allowing them to serve a bacteriocidal or bacteriostatic function. In humans (and other mammals) bile acids are normally conjugated with the amino acids glycine and taurine by the liver. This conjugation catalyzed by two liver enzymes, bile acid CoA ligase (BAL) and bile acid CoA: amino acid N-acyltransferase (BAT). Glycine and taurine bound BAs are also referred to as bile salts due to their decreased pKa and complete ionization resulting in these compounds being present as anions in vivo. Unlike glycine and taurine-conjugated bile acids, these recently discovered bile acids, such as Chenodeoxycholylvaline, are produced by the gut microbiota, making them secondary bile acids (PMID: 32103176 ) or microbially conjugated bile acids (MCBAs) (PMID: 34127070 ). Evidence suggests that these bile acid-amino acid conjugates are produced by microbes belonging to Clostridia species (PMID: 32103176 ). These unusual bile acid-amino acid conjugates are found in higher frequency in patients with inflammatory bowel disease (IBD), cystic fibrosis (CF) and in infants (PMID: 32103176 ). Chenodeoxycholylvaline appears to act as an agonist for the farnesoid X receptor (FXR) and it can also lead to reduced expression of bile acid synthesis genes (PMID: 32103176 ). It currently appears that microbially conjugated bile acids (MCBAs) or amino acid-bile acid conjugates are only conjugated to cholic acid, deoxycholic acid and chenodeoxycholic acid (PMID: 34127070 ). It has been estimated that if microbial conjugation of bile acids is very promiscuous and occurs for all potential oxidized, epimerized, and dehydroxylated states of each hydroxyl group present on cholic acid (C3, C7, C12) in addition to ring orientation, the total number of potential human bile acid conjugates could be over 2800 (PMID: 34127070 ).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC29H49NO5
Average Molecular Weight491.713
Monoisotopic Molecular Weight491.361073682
IUPAC Name2-(4-{5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)-3-methylbutanoic acid
Traditional Name2-(4-{5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}pentanamido)-3-methylbutanoic acid
CAS Registry NumberNot Available
SMILES
CC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CCC12C)C(O)=O
InChI Identifier
InChI=1S/C29H49NO5/c1-16(2)26(27(34)35)30-24(33)9-6-17(3)20-7-8-21-25-22(11-13-29(20,21)5)28(4)12-10-19(31)14-18(28)15-23(25)32/h16-23,25-26,31-32H,6-15H2,1-5H3,(H,30,33)(H,34,35)
InChI KeyDWKUILAFNXKAFN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as glycinated bile acids and derivatives. Glycinated bile acids and derivatives are compounds with a structure characterized by the presence of a glycine linked to a bile acid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentGlycinated bile acids and derivatives
Alternative Parents
Substituents
  • Glycinated bile acid
  • Dihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • 7-hydroxysteroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • Valine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Fatty acyl
  • N-acyl-amine
  • Fatty amide
  • Cyclic alcohol
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.9ALOGPS
logP4.06ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.92ChemAxon
pKa (Strongest Basic)-0.39ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area106.86 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity135.57 m³·mol⁻¹ChemAxon
Polarizability57.8 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-245.48530932474
DeepCCS[M+Na]+220.71430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ChenodeoxycholylvalineCC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CCC12C)C(O)=O3212.4Standard polar33892256
ChenodeoxycholylvalineCC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CCC12C)C(O)=O3169.5Standard non polar33892256
ChenodeoxycholylvalineCC(C)C(NC(=O)CCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CCC12C)C(O)=O4089.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chenodeoxycholylvaline,4TMS,isomer #1CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C)[Si](C)(C)C3809.3Semi standard non polar33892256
Chenodeoxycholylvaline,4TMS,isomer #1CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C)[Si](C)(C)C3885.7Standard non polar33892256
Chenodeoxycholylvaline,4TMS,isomer #1CC(C)C(C(=O)O[Si](C)(C)C)N(C(=O)CCC(C)C1CCC2C3C(O[Si](C)(C)C)CC4CC(O[Si](C)(C)C)CCC4(C)C3CCC12C)[Si](C)(C)C4152.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chenodeoxycholylvaline GC-MS (Non-derivatized) - 70eV, Positivesplash10-01u1-0212900000-f880a4498a3ddee4e2102021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chenodeoxycholylvaline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chenodeoxycholylvaline 10V, Positive-QTOFsplash10-0002-0003900000-5fef8953bd3fdb7526d12021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chenodeoxycholylvaline 20V, Positive-QTOFsplash10-0a6r-1509500000-4c886595bb78182ad4832021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chenodeoxycholylvaline 40V, Positive-QTOFsplash10-054k-9654000000-66264f9191483e65c98f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chenodeoxycholylvaline 10V, Negative-QTOFsplash10-0006-0000900000-ab03d857758aa85e5c6e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chenodeoxycholylvaline 20V, Negative-QTOFsplash10-00dl-0108900000-af79c60831afb3216e682021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chenodeoxycholylvaline 40V, Negative-QTOFsplash10-05fu-2009000000-7d9dbf25f8481c73821d2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue Locations
  • Intestine
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID9379926
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11204859
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Guzior DV, Quinn RA: Review: microbial transformations of human bile acids. Microbiome. 2021 Jun 14;9(1):140. doi: 10.1186/s40168-021-01101-1. [PubMed:34127070 ]
  2. Quinn RA, Melnik AV, Vrbanac A, Fu T, Patras KA, Christy MP, Bodai Z, Belda-Ferre P, Tripathi A, Chung LK, Downes M, Welch RD, Quinn M, Humphrey G, Panitchpakdi M, Weldon KC, Aksenov A, da Silva R, Avila-Pacheco J, Clish C, Bae S, Mallick H, Franzosa EA, Lloyd-Price J, Bussell R, Thron T, Nelson AT, Wang M, Leszczynski E, Vargas F, Gauglitz JM, Meehan MJ, Gentry E, Arthur TD, Komor AC, Poulsen O, Boland BS, Chang JT, Sandborn WJ, Lim M, Garg N, Lumeng JC, Xavier RJ, Kazmierczak BI, Jain R, Egan M, Rhee KE, Ferguson D, Raffatellu M, Vlamakis H, Haddad GG, Siegel D, Huttenhower C, Mazmanian SK, Evans RM, Nizet V, Knight R, Dorrestein PC: Global chemical effects of the microbiome include new bile-acid conjugations. Nature. 2020 Mar;579(7797):123-129. doi: 10.1038/s41586-020-2047-9. Epub 2020 Feb 26. [PubMed:32103176 ]