ContaminantDB: Captopril

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 04:23:28 UTC

Update Date

2016-11-09 01:15:36 UTC

Accession Number

CHEM017481

Identification

Common Name

Captopril

Class

Small Molecule

Description

Captopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE), the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Captopril may be used in the treatment of hypertension.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2S)-1-[(2S)-2-Methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid	ChEBI
Acepress	ChEBI
Apopril	ChEBI
Capoten	ChEBI
Captolane	ChEBI
Captoprilum	ChEBI
Captopryl	ChEBI
Captoril	ChEBI
Cesplon	ChEBI
CP	ChEBI
D-2-Methyl-3-mercaptopropanoyl-L-proline	ChEBI
D-3-Mercapto-2-methylpropanoyl-L-proline	ChEBI
Dilabar	ChEBI
Garranil	ChEBI
Hypertil	ChEBI
L-Captopril	ChEBI
Lopirin	ChEBI
Tenosbon	ChEBI
Tensobon	ChEBI
Tensoprel	ChEBI
(2S)-1-[(2S)-2-Methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylate	Generator
(2S)-1-[(2S)-2-Methyl-3-sulphanylpropanoyl]pyrrolidine-2-carboxylate	Generator
(2S)-1-[(2S)-2-Methyl-3-sulphanylpropanoyl]pyrrolidine-2-carboxylic acid	Generator
(S)-1-(3-Mercapto-2-methyl-1-oxopropyl)-L-proline	HMDB

Chemical Formula

C₉H₁₅NO₃S

Average Molecular Mass

217.285 g/mol

Monoisotopic Mass

217.077 g/mol

CAS Registry Number

62571-86-2

IUPAC Name

(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

captopril

SMILES

C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O

InChI Identifier

InChI=1S/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1

InChI Key

FAKRSMQSSFJEIM-RQJHMYQMSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline 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

Proline and derivatives

Alternative Parents

Substituents

N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
N-acyl-l-alpha-amino acid
Proline or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid
Monocarboxylic acid or derivatives
Alkylthiol
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organosulfur compound
Carbonyl group
Organic oxide
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

L-proline derivative (CHEBI:3380 )
alkanethiol (CHEBI:3380 )
pyrrolidinemonocarboxylic acid (CHEBI:3380 )
N-acylpyrrolidine (CHEBI:3380 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.52 g/L	ALOGPS
logP	1.02	ALOGPS
logP	0.73	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	4.02	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.61 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.63 m³·mol⁻¹	ChemAxon
Polarizability	21.72 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9400000000-51d6dae57d8b305064ac	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9410000000-65f35f9df00d94abb290	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-014i-0940000000-26ddf220b67fb8dcdff0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-001i-0910000000-8797427ebbfead8313f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0940000000-26ddf220b67fb8dcdff0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-01b9-8910000000-d831e8d48402a4c5fe73	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-01b9-9720000000-8218e12ef8f7e988c312	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0490000000-368990ca74ad93e14251	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0290000000-1fecd0b4a33bc6afc4f2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-01b9-0940000000-089a033b51be30f3a297	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-3950000000-02525f49c5ae7c64e751	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00di-9100000000-2d3dff49389d32966270	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-00di-9000000000-5fec50f211615a61cd58	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-9200000000-955e87fa6bbc3b688dc5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-9300000000-12f0a42fb63fd9a341e4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-00di-9100000000-8a3f39d9e1f9e0ddfa3a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-01b9-9720000000-cc5d5a56e386ed3da5df	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-001i-0910000000-8797427ebbfead8313f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-014i-4920000000-abe7ab7a43bb4ab37f27	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0390000000-443943c884569fe9bdde	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-2950000000-6310d54f5354a953ff47	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0890000000-6471cadb8251b2cde228	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-3920000000-93e7eef38f7bf8d57f56	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9400000000-f8b12a12ec76d0508922	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-1930000000-21d83329a778cc965f80	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00yr-2910000000-30e872740f7cb996700d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-015c-9500000000-9c8558c81f9491de8c08	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum