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Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2017-03-02 21:33:23 UTC
HMDB IDHMDB14663
Secondary Accession NumbersNone
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 Bentiromide is not available in the U.S. or Canada (It was withdrawn in the US in October 1996).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
Thumb
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-pabaMeSH
PABA-peptideMeSH
Benzoyl-tyrosyl-pabaMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as tyrosine and derivatives. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
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
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Diagnostic aids
  • Indicators and Reagents
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point241 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.12e-03 g/LNot Available
LogP3.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0041 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity112.75 m3·mol-1ChemAxon
Polarizability42.16 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00522
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00522
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00522
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5329364
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBentiromide
NuGOwiki LinkHMDB14663
Metagene LinkHMDB14663
METLIN IDNot Available
PubChem Compound6957673
PDB IDNot Available
ChEBI ID31263
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. [6371722 ]