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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:05 UTC
HMDB IDHMDB0014663
Secondary Accession Numbers
  • HMDB14663
Metabolite Identification
Common NameBentiromide
DescriptionBentiromide is a peptide used as a screening test for exocrine pancreatic insufficiency and to monitor the adequacy of supplemental pancreatic therapy. It is given by mouth as a noninvasive test. The amount of 4-aminobenzoic acid and its metabolites excreted in the urine is taken as a measure of the chymotrypsin-secreting activity of the pancreas. Headache and gastrointestinal disturbances have been reported in patients taking bentiromide. Bentiromide is not available in the U.S. or Canada (It was withdrawn in the US in October 1996).
Structure
Data?1582753205
Synonyms
ValueSource
(S)-4-((2-(Benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl)amino)benzoic acidChEBI
(S)-p-(alpha-Benzamido-p-hydroxyhydrocinnamamido)benzoic acidChEBI
4-(N-Benzoyl-L-tyrosylamino)benzoic acidChEBI
BentiromidoChEBI
BentiromidumChEBI
Benzoyltyrosyl-p-aminobenzoic acidChEBI
BT-PABAChEBI
BTPABAChEBI
N-Benzoyl-L-tyrosyl-p-aminobenzoateChEBI
N-Benzoyl-L-tyrosyl-p-aminobenzoic acidChEBI
PFDChEBI
PFTChEBI
(S)-4-((2-(Benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl)amino)benzoateGenerator
(S)-p-(a-Benzamido-p-hydroxyhydrocinnamamido)benzoateGenerator
(S)-p-(a-Benzamido-p-hydroxyhydrocinnamamido)benzoic acidGenerator
(S)-p-(alpha-Benzamido-p-hydroxyhydrocinnamamido)benzoateGenerator
(S)-p-(Α-benzamido-p-hydroxyhydrocinnamamido)benzoateGenerator
(S)-p-(Α-benzamido-p-hydroxyhydrocinnamamido)benzoic acidGenerator
4-(N-Benzoyl-L-tyrosylamino)benzoateGenerator
Benzoyltyrosyl-p-aminobenzoateGenerator
N-Benzoyl-L-tyrosyl-pabaHMDB
PABA-peptideHMDB
Benzoyl-tyrosyl-pabaHMDB
Chemical FormulaC23H20N2O5
Average Molecular Weight404.4153
Monoisotopic Molecular Weight404.13722176
IUPAC Name4-[(2S)-3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]benzoic acid
Traditional Namebentiromide
CAS Registry Number37106-97-1
SMILES
OC(=O)C1=CC=C(NC(=O)[C@H](CC2=CC=C(O)C=C2)NC(=O)C2=CC=CC=C2)C=C1
InChI Identifier
InChI=1S/C23H20N2O5/c26-19-12-6-15(7-13-19)14-20(25-21(27)16-4-2-1-3-5-16)22(28)24-18-10-8-17(9-11-18)23(29)30/h1-13,20,26H,14H2,(H,24,28)(H,25,27)(H,29,30)/t20-/m0/s1
InChI KeySPPTWHFVYKCNNK-FQEVSTJZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tyrosine and derivatives. Tyrosine and derivatives are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentTyrosine and derivatives
Alternative Parents
Substituents
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • Hippuric acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Acylaminobenzoic acid or derivatives
  • Alpha-amino acid amide
  • Amphetamine or derivatives
  • Benzoic acid or derivatives
  • Anilide
  • Benzoic acid
  • Benzamide
  • N-arylamide
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Fatty amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point241 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0041 g/LNot Available
LogP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0041 g/LALOGPS
logP2.99ALOGPS
logP3.54ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area115.73 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity112.74 m³·mol⁻¹ChemAxon
Polarizability42.16 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-0951000000-3408813d239b684fcca1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0a59-0902130000-2e52e28c1a3b2bc381ceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0479500000-9b7d3992e6800b7ec069Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4l-0951000000-0e8e632e5411e48e747eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-2920000000-786eb7e2b52e3322399dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0254900000-a07141fcfe2759e41e1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zg3-3694200000-da9c1e7b3b855e5436e0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6900000000-d9bd094cd00bd79ca2a7Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00522 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00522 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00522
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5329364
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBentiromide
METLIN IDNot Available
PubChem Compound6957673
PDB IDNot Available
ChEBI ID31263
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Toskes PP: The bentiromide test for pancreatic exocrine insufficiency. Pharmacotherapy. 1984 Mar-Apr;4(2):74-80. [PubMed:6371722 ]