ChemFOnt: Showing chemical card for Bentiromide (CFc000009019)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:01 UTC

Chemfont ID

CFc000009019

Molecule Identification

Common Name

Bentiromide

Definition

Bentiromide 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 Bentiromide is not available in the U.S. or Canada (It was withdrawn in the US in October 1996).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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(S)-4-((2-(Benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl)amino)benzoic acid	ChEBI
(S)-p-(alpha-Benzamido-p-hydroxyhydrocinnamamido)benzoic acid	ChEBI
4-(N-Benzoyl-L-tyrosylamino)benzoic acid	ChEBI
Bentiromido	ChEBI
Bentiromidum	ChEBI
Benzoyltyrosyl-p-aminobenzoic acid	ChEBI
BT-PABA	ChEBI
BTPABA	ChEBI
N-Benzoyl-L-tyrosyl-p-aminobenzoate	ChEBI
N-Benzoyl-L-tyrosyl-p-aminobenzoic acid	ChEBI
PFD	ChEBI
PFT	ChEBI
(S)-4-((2-(Benzoylamino)-3-(4-hydroxyphenyl)-1-oxopropyl)amino)benzoate	Generator
(S)-p-(a-Benzamido-p-hydroxyhydrocinnamamido)benzoate	Generator
(S)-p-(a-Benzamido-p-hydroxyhydrocinnamamido)benzoic acid	Generator
(S)-p-(alpha-Benzamido-p-hydroxyhydrocinnamamido)benzoate	Generator
(S)-p-(Α-benzamido-p-hydroxyhydrocinnamamido)benzoate	Generator
(S)-p-(Α-benzamido-p-hydroxyhydrocinnamamido)benzoic acid	Generator
4-(N-Benzoyl-L-tyrosylamino)benzoate	Generator
Benzoyltyrosyl-p-aminobenzoate	Generator
N-Benzoyl-L-tyrosyl-paba	HMDB
PABA-peptide	HMDB
Benzoyl-tyrosyl-paba	HMDB

Chemical Formula

C₂₃H₂₀N₂O₅

Average Molecular Weight

404.4153

Monoisotopic Molecular Weight

404.13722176

IUPAC Name

4-[(2S)-3-(4-hydroxyphenyl)-2-(phenylformamido)propanamido]benzoic acid

Traditional Name

bentiromide

CAS Registry Number

37106-97-1

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 Key

SPPTWHFVYKCNNK-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Tyrosine 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

dipeptide (CHEBI:31263 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014663)

Source

Exogenous

Exogenous (HMDB: HMDB0014663)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0041 g/L	ALOGPS
logP	2.99	ALOGPS
logP	3.54	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.16	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.73 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	112.74 m³·mol⁻¹	ChemAxon
Polarizability	42.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0014663

DrugBank ID

DB00522

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5329364

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bentiromide

METLIN ID

Not Available

PubChem Compound

6957673

PDB ID

Not Available

ChEBI ID

31263

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Bentiromide (CFc000009019)

MOL for CFc000009019 (Bentiromide)

3D MOL for CFc000009019 (Bentiromide)

3D SDF for CFc000009019 (Bentiromide)

3D-SDF for CFc000009019 (Bentiromide)

PDB for CFc000009019 (Bentiromide)

3D PDB for CFc000009019 (Bentiromide)

SMILES for CFc000009019 (Bentiromide)

INCHI for CFc000009019 (Bentiromide)

Structure for CFc000009019 (Bentiromide)

3D Structure for CFc000009019 (Bentiromide)