| In ZINC since | Heavy atoms | Benign functionality |
|---|---|---|
| September 27th, 2005 | 14 | No |
Popular Name: Captopril Captopril
Find On: PubMed — Wikipedia — Google
CAS Numbers: 62571-86-2 , [62571-86-2]
(2S)-1-(3-Mercapto-2-methylpropionyl)-L-proline
(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
(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
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
3-Mercapto-2-methylpropionyl-proline
62571-86-2; Apopril (TN); Capoten (TN); Captopril (JP16/USP/INN); D00251
62571-86-2; Captopril; Prestwick_103
CAPTOPRIL; CPD000059061; SAM002564201
Captoprilum [INN-Latin];Captopryl;L-Captopril
D-2-Methyl-3-mercaptopropanoyl-L-proline
D-3-Mercapto-2-methylpropanoyl-L-proline
D-3-Mercapto-2-methylpropionylproline
L-Proline, 1-((2S)-3-mercapto-2-methyl-1-oxopropyl)-
L-Proline, 1-(3-mercapto-2-methyl-1-oxopropyl)-, (S)-
| 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 | ↓ |
| 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 |
| 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 |
| 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_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 |
| ACE_RAT | P47820 | Angiotensin-converting Enzyme, Rat | 11 | 0.80 | 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 |
| Description | Species |
|---|---|
| Metabolism of Angiotensinogen to Angiotensins |
| 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 |
