UCSF

ZINC00057001

Substance Information

In ZINC since Heavy atoms Benign functionality
September 27th, 2005 14 No

CAS Numbers: 62571-86-2 , [62571-86-2]

Other Names:

(2S)-1-(3-Mercapto-2-methylpropionyl)-L-proline

(2S)-1-(3-Mercapto-2-methylpropionyl)-L-proline; (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid; CPD0-2067; D-2-Methyl-3-mercaptopropanoyl-L-proline; D-3-Mercapto-2-methylpropionylproline; captopril

(2S)-1-(3-Mercapto-2-methylpropionyl)-L-proline; (S)-1-(3-Mercapto-2-methyl-1-oxopropyl)-L-proline; 1-((2S)-3-Mercapto-2-methylpropionyl)-L-proline; 1-(3-Mercapto-2-methyl-1-oxopropyl)-L-proline; 1-(D-3-Mercapto-2-methyl-1-oxopropyl)-L-proline (S,S); 1-Py

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

(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid; CP; Captopryl; D-2-methyl-3-mercaptopropanoyl-L-proline; D-3-mercapto-2-methylpropanoyl-L-proline; L-Captopril

(S)-1-((S)-3-Mercapto-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid

(S)-1-(3-Mercapto-2-methyl-1-oxo-propyl)-L-proline

(S)-1-(3-Mercapto-2-methyl-1-oxopropyl)-L-proline

pril

1-((2S)-3-Mercapto-2-methylpropionyl)-L-proline

1-(3-Mercapto-2-methyl-1-oxopropyl)-L-proline

1-(D-3-Mercapto-2-methyl-1-oxopropyl)-L-proline (S,S)

1-Pyrrolidinecarboxylic acid, 1-(D-3-mercapto-2-methyl-1-propionyl)-, L-(S,S)-

1-[(2S)-2-methyl-3-sulfanylpropanoyl]-L-proline

1j37

3-Mercapto-2-methylpropionyl-proline

62571-86-2

62571-86-2; Apopril (TN); Capoten (TN); Captopril (JP16/USP/INN); D00251

62571-86-2; Captopril; Prestwick_103

AC-12047

AC1L2B4L

AC1Q29GZ

AC1Q5R48

Acediur

Acenorm

Aceplus

Acepress

Acepress; Apopril; Capoten; Captolane; Captoril; Cesplon; Dilabar; Garranil; Hypertil; Lopirin; Tenosbon; Tensobon; Tensoprel

Acepril

Alopresin

Apopril

Apopril (TN)

Asisten

BB_NC-2104

BIM-0050290.0001

BPBio1_000063

BRD-K54529596-001-04-0

BSPBio_000057

BSPBio_002976

C 4042

C4042_SIAL

C4042_SIGMA

C8856_SIAL

C9H15NO3S

Capace

Capoten

Capoten (TN)

Captolane

Captopril (BAN

Captopril (Capoten)

Captopril (JP15/USP/INN)

Captopril [USAN:INN:BAN:JAN]

Captopril, 98%

captopril; captoprilum

CAPTOPRIL; CPD000059061; SAM002564201

Captoprilum

Captoprilum [INN-Latin]

Captoprilum [INN-Latin];Captopryl;L-Captopril

Captopryl

Captoril

Captril

Cesplon

CHEBI:3380

CHEMBL1560

CHEMBL82

CID44093

CPD0-2067

CPD000059061

D-2-Methyl-3-mercaptopropanoyl-L-proline

D-3-Mercapto-2-methylpropanoyl-L-proline

D-3-Mercapto-2-methylpropionylproline

D00251

DAP000589

DB01197

Dilabar

DivK1c_000208

EINECS 263-607-1

EU-0100302

FDA

FT-0082749

Garranil

Garranil (discontinued)

Hipertil

HMS1921C12

HMS2089P19

HMS2092I12

HMS500K10

HSDB 6527

Hypertil

IDI1_000208

INN

Isopresol

JAN

KBio1_000208

KBio2_001168

KBio2_003736

KBio2_006304

KBio3_002196

KBioGR_001321

KBioSS_001168

L-Captopril

L-Proline, 1-((2S)-3-mercapto-2-methyl-1-oxopropyl)-

L-Proline, 1-(3-mercapto-2-methyl-1-oxopropyl)-, (S)-

Lopirin

Lopirin [Switzerland]

Lopril

LS-137465

MCO

MFCD00168073

MLS000069484

MLS001076488

MolPort-001-794-639

N-[(S)-3-Mercapto-2-methylpropionyl]-L-proline

N/A

NCGC00015235-01

NCGC00015235-02

NCGC00023654-03

NCGC00023654-04

NCGC00023654-05

NCGC00023654-06

NCGC00023654-07

NCGC00023654-08

NCGC00023654-09

NCGC00023654-10

NINDS_000208

Prestwick3_000019

Prestwick_103

QA-3169

SA 333

SAM002564201

SMP1_000056

SMR000059061

SPBio_001022

SPECTRUM1500682

Spectrum2_001211

Spectrum3_001388

Spectrum4_000811

Spectrum5_001587

Spectrum_000688

SQ 14,225

SQ 14225

SQ-14,225

SQ-14,534

SQ-14225

SQ-14534

ST079562

STK802012

Tenosbon

Tensiomin

Tensobon

Tensoprel

UNII-9G64RSX1XD

UPCMLD-DP003

UPCMLD-DP003:001

USAN

USP)

X8Z

[2S]-1-[3-Mercapto-2-methylpropionyl]-L-proline

Download: MOL2 SDF SMILES Flexibase

Annotations

Vendors

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) -1.09 5.14 -56.41 0 4 -1 60 216.282 3

Vendor Notes

Note Type Comments Provided By
biological_use Antihypertensive agent ZereneX Building Blocks
Mp [°C] 103 - 108 Acros Organics
MP 106 TCI
ALOGPS_SOLUBILITY 4.52e+00 g/l DrugBank-approved
purity 9.500000000000000e+001 Enamine Building Blocks Enamine Building Blocks
Purity 95% Fluorochem
mechanism ACE inhibitor IBScreen Bioactives IBScreen Bioactives
UniProt Database Links ACE2_HUMAN; ACE2_RAT; ACER_DROME; ACE_DROME; ACE_HUMAN; ACE_MOUSE; ACE_THETS; ULIL_METAC ChEBI
mechanism angiotensin-antagonist IBScreen Bioactives
Therapy Angiotensin-converting enzyme (ACE) inhibitor; antihypertensive SMDC Iconix
Indications antihypertensive KeyOrganics Bioactives
biological_use Antihypertensive agent IBScreen Bioactives IBScreen Bioactives
mechanism apparent primary action involves suppression of the renin-angiotensin-aldosterone-system IBScreen Bioactives
mechanism decrease in plasma-volume IBScreen Bioactives
mechanism decreases plasma-angiotensin-2 concentration IBScreen Bioactives
biological_use Drug used for diagnosis and treatment of renin-dependent hypertension IBScreen Bioactives
Patent Database Links EP0795327; EP0889031; EP1479666; EP1491541; EP1533292; EP1541175; EP1553091; EP1559424; EP1579862; EP1602334; EP1611886; EP1627638; EP1669345; EP1671632; EP1690530; EP1705184; EP1717226; EP1723962; EP1741713; EP1746099; EP1776954; EP1785144; EP1790353; EP ChEBI
biological_use Exp. drug for treatment of myocardial infarction IBScreen Bioactives
H phrase H315: Causes skin irritation Acros Organics
H phrase H315: Causes skin irritation; H335: May cause respiratory irritation; H319: Causes serious eye irritation Acros Organics
mechanism increased plasma-renin causes decrease in aldosterone-secretion resulting in: small increases in serum-potassium IBScreen Bioactives
mechanism increased sodium-excretion IBScreen Bioactives
mechanism increases plasma levels of PGE2 and PGE2-alpha metabolites. IBScreen Bioactives
mechanism increases plasma-renin activity resulting from loss of negative feedback on renin release due to reduced angiotensin-2 concentration IBScreen Bioactives
mechanism Increases urinary excretion of PGE2 IBScreen Bioactives
mechanism May increase prostaglandin synthesis IBScreen Bioactives
mechanism May inhibit local angiotensin 2 at vascular and renal sites so attenuating catecholamine release IBScreen Bioactives
PUBCHEM_SUBSTANCE_COMMENT NCC_SAMPLE_SUPPLIER : LightBiologicals; NCC_SUPPLIER_STRUCTURE_ID : C-5737; NCC_SUPPLIER_SAMPLE_COMMENTS : WHITE POWDER NIH Clinical Collection via PubChem
P phrase P261: Avoid breathing dust/fume/gas/mist/vapors/spray Acros Organics
P phrase P261: Avoid breathing dust/fume/gas/mist/vapors/spray; P302+ P352: IF ON SKIN: Wash with plenty of soap and water; P280: Wear protective gloves/protective clothing/eye protection/face protection; P305 + P351 + P338: IF IN EYES: Rinse cautiously with water Acros Organics
R phrase R36/37/38: Irritating to eyes, respiratory system and skin. Acros Organics
Target RAAS Selleck Chemicals
S phrase S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Acros Organics
S phrase S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S37/39: Wear suitable gloves and eye/face protection. Acros Organics
PUBCHEM_SUBSTANCE_COMMENT SAMPLE_SUPPLIER: LightBiologicals; SUPPLIER_STRUCTURE_ID: C-5737; SUPPLIER_COMMENTS: WHITE POWDER NIH Clinical Collection via PubChem
biological_use Smooth muscle relaxant IBScreen Bioactives
Hazard XI: Irritant Acros Organics

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
ACE-1-E Angiotensin-converting Enzyme (cluster #1 Of 1), Eukaryotic Eukaryotes 23 0.76 Binding ≤ 10μM
ACE-1-E Angiotensin-converting Enzyme (cluster #1 Of 1), Eukaryotic Eukaryotes 70 0.72 Binding ≤ 10μM
ACE2-1-E Angiotensin-converting Enzyme 2 (cluster #1 Of 1), Eukaryotic Eukaryotes 9 0.80 Binding ≤ 10μM
AMPB-1-E Aminopeptidase B (cluster #1 Of 2), Eukaryotic Eukaryotes 2000 0.57 Binding ≤ 10μM
AMPE-1-E Aminopeptidase A (cluster #1 Of 2), Eukaryotic Eukaryotes 2000 0.57 Binding ≤ 10μM
AMPN-1-E Aminopeptidase N (cluster #1 Of 5), Eukaryotic Eukaryotes 2000 0.57 Binding ≤ 10μM
LKHA4-2-E Leukotriene A4 Hydrolase (cluster #2 Of 2), Eukaryotic Eukaryotes 70 0.72 Binding ≤ 10μM
RENI-1-E Renin (cluster #1 Of 1), Eukaryotic Eukaryotes 2 0.87 Binding ≤ 10μM
THRB-1-E Prothrombin (cluster #1 Of 8), Eukaryotic Eukaryotes 48 0.73 Binding ≤ 10μM
DAPE-1-B Succinyl-diaminopimelate Desuccinylase (cluster #1 Of 1), Bacterial Bacteria 3300 0.55 Binding ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
ACE_RAT P47820 Angiotensin-converting Enzyme, Rat 11 0.80 Binding ≤ 1μM
ACE_RABIT P12822 Angiotensin-converting Enzyme, Rabit 0.1 1.00 Binding ≤ 1μM
ACE_HUMAN P12821 Angiotensin-converting Enzyme, Human 0.12 0.99 Binding ≤ 1μM
ACE2_HUMAN Q9BYF1 Angiotensin-converting Enzyme 2, Human 10 0.80 Binding ≤ 1μM
LKHA4_HUMAN P09960 Leukotriene A4 Hydrolase, Human 70 0.72 Binding ≤ 1μM
RENI_HUMAN P00797 Renin, Human 1.7 0.88 Binding ≤ 1μM
THRB_HUMAN P00734 Thrombin, Human 48 0.73 Binding ≤ 1μM
AMPE_HUMAN Q07075 Aminopeptidase A, Human 2000 0.57 Binding ≤ 10μM
AMPB_HUMAN Q9H4A4 Aminopeptidase B, Human 2000 0.57 Binding ≤ 10μM
AMPN_HUMAN P15144 Aminopeptidase N, Human 2000 0.57 Binding ≤ 10μM
ACE_RAT P47820 Angiotensin-converting Enzyme, Rat 11 0.80 Binding ≤ 10μM
ACE_RABIT P12822 Angiotensin-converting Enzyme, Rabit 0.1 1.00 Binding ≤ 10μM
ACE_HUMAN P12821 Angiotensin-converting Enzyme, Human 0.12 0.99 Binding ≤ 10μM
ACE2_HUMAN Q9BYF1 Angiotensin-converting Enzyme 2, Human 10 0.80 Binding ≤ 10μM
LKHA4_HUMAN P09960 Leukotriene A4 Hydrolase, Human 10000 0.50 Binding ≤ 10μM
RENI_HUMAN P00797 Renin, Human 1.7 0.88 Binding ≤ 10μM
DAPE_HAEIN P44514 Succinyl-diaminopimelate Desuccinylase, Haein 1820 0.57 Binding ≤ 10μM
THRB_HUMAN P00734 Thrombin, Human 48 0.73 Binding ≤ 10μM

Direct Reactome Annotations (via ChEBI)

Description Species
Metabolism of Angiotensinogen to Angiotensins

Reactome Annotations from Targets (via Uniprot)

Description Species
Cell surface interactions at the vascular wall
Common Pathway
G alpha (q) signalling events
Gamma-carboxylation of protein precursors
Intrinsic Pathway
Metabolism of Angiotensinogen to Angiotensins
Peptide ligand-binding receptors
Platelet Aggregation (Plug Formation)
Regulation of Insulin-like Growth Factor (IGF) transport and uptake by Insulin-l
Removal of aminoterminal propeptides from gamma-carboxylated proteins
Synthesis of Leukotrienes (LT) and Eoxins (EX)
Thrombin signalling through proteinase activated receptors (PARs)
Transport of gamma-carboxylated protein precursors from the endoplasmic reticulu

Analogs ( Draw Identity 99% 90% 80% 70% )