(S)-2-(2-Formyl-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid benzyl ester

ID: ALA79993

Chembl Id: CHEMBL79993

Cas Number: 88795-32-8

PubChem CID: 122623

Max Phase: Preclinical

Molecular Formula: C18H22N2O4

Molecular Weight: 330.38

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Synonyms: JTP-4819 | Z-Pro-prolinal|N-Benzyloxycarbonylprolylprolinal|n-benzyloxycarbonyl-l-prolyl-l-prolinal|N-Benzyloxycarbonyl-prolyl-prolinal|z-prolyl-prolinal|88795-32-8|4YM8D0GKX6|CHEMBL79993|Z-PP-CHO|Prolyl Endopeptidase Inhibitor II|Boc-Pro-prolinal;(Boc)-Prolyl-prolinal;BPP|BRN 4821785|UNII-4YM8D0GKX6|benzyl (2S)-2-[(2S)-2-formylpyrrolidine-1-carbonyl]pyrrolidine-1-carboxylate|BSPBio_001545|KBioGR_000265|KBioSS_000265|benzyl 2-(2-formylpyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate|SCHEMBL12193Show More

Canonical SMILES:  O=C[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)OCc1ccccc1

Standard InChI:  InChI=1S/C18H22N2O4/c21-12-15-8-4-10-19(15)17(22)16-9-5-11-20(16)18(23)24-13-14-6-2-1-3-7-14/h1-3,6-7,12,15-16H,4-5,8-11,13H2/t15-,16-/m0/s1

Standard InChI Key:  ORZXYSPOAVJYRU-HOTGVXAUSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

PREP Tchem Prolyl endopeptidase (1176 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CELA1 Tchem Elastase 1 (40 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPT Tclin Microtubule-associated protein tau (95507 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
VDR Tclin Vitamin D receptor (26531 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BCHE Tclin Butyrylcholinesterase (7174 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHE Tclin Acetylcholinesterase (18204 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FAP Tchem Fibroblast activation protein alpha (827 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

PREP Prolyl endopeptidase (246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Prep Prolyl endopeptidase (113 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
f1pep1 Prolyl endopeptidase (3 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Prep Prolyl endopeptidase (55 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PREP Prolyl endopeptidase (14 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 330.38Molecular Weight (Monoisotopic): 330.1580AlogP: 1.98#Rotatable Bonds: 4
Polar Surface Area: 66.92Molecular Species: NEUTRALHBA: 4HBD:
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): #RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: CX LogP: 1.43CX LogD: 1.43
Aromatic Rings: 1Heavy Atoms: 24QED Weighted: 0.79Np Likeness Score: -0.29

References

1. Tanaka Y, Niwa S, Nishioka H, Yamanaka T, Torizuka M, Yoshinaga K, Kobayashi N, Ikeda Y, Arai H..  (1994)  New potent prolyl endopeptidase inhibitors: synthesis and structure-activity relationships of indan and tetralin derivatives and their analogues.,  37  (13): [PMID:8027988] [10.1021/jm00039a019]
2. Portevin B, Benoist A, Rémond G, Hervé Y, Vincent M, Lepagnol J, De Nanteuil G..  (1996)  New prolyl endopeptidase inhibitors: in vitro and in vivo activities of azabicyclo[2.2.2]octane, azabicyclo[2.2.1]heptane, and perhydroindole derivatives.,  39  (12): [PMID:8691432] [10.1021/jm950858c]
3. Wallén EA, Christiaans JA, Forsberg MM, Venäläinen JI, Männistö PT, Gynther J..  (2002)  Dicarboxylic acid bis(L-prolyl-pyrrolidine) amides as prolyl oligopeptidase inhibitors.,  45  (20): [PMID:12238937] [10.1021/jm020966g]
4. Jarho EM, Wallén EA, Christiaans JA, Forsberg MM, Venäläinen JI, Männistö PT, Gynther J, Poso A..  (2005)  Dicarboxylic acid azacycle l-prolyl-pyrrolidine amides as prolyl oligopeptidase inhibitors and three-dimensional quantitative structure-activity relationship of the enzyme-inhibitor interactions.,  48  (15): [PMID:16033257] [10.1021/jm0500020]
5. Ahmad VU, Hussain H, Jassbi AR, Hussain J, Bukhari IA, Yasin A, Aziz N, Choudhary MI..  (2003)  New bioactive diterpene polyesters from Euphorbia decipiens.,  66  (9): [PMID:14510601] [10.1021/np020186a]
6. Song KS, Raskin I..  (2002)  A prolyl endopeptidase-inhibiting benzofuran dimer from Polyozellus multiflex.,  65  (1): [PMID:11809072] [10.1021/np010194b]
7. Lawandi J, Gerber-Lemaire S, Juillerat-Jeanneret L, Moitessier N..  (2010)  Inhibitors of prolyl oligopeptidases for the therapy of human diseases: defining diseases and inhibitors.,  53  (9): [PMID:20058865] [10.1021/jm901104g]
8. Racys DT, Rea D, Fülöp V, Wills M..  (2010)  Inhibition of prolyl oligopeptidase with a synthetic unnatural dipeptide.,  18  (13): [PMID:20627594] [10.1016/j.bmc.2010.05.012]
9. PubChem BioAssay data set, 
10. Mariaule G, De Cesco S, Airaghi F, Kurian J, Schiavini P, Rocheleau S, Huskić I, Auclair K, Mittermaier A, Moitessier N..  (2016)  3-Oxo-hexahydro-1H-isoindole-4-carboxylic Acid as a Drug Chiral Bicyclic Scaffold: Structure-Based Design and Preparation of Conformationally Constrained Covalent and Noncovalent Prolyl Oligopeptidase Inhibitors.,  59  (9): [PMID:26619267] [10.1021/acs.jmedchem.5b01296]
11. Hostalkova A, Marikova J, Opletal L, Korabecny J, Hulcova D, Kunes J, Novakova L, Perez DI, Jun D, Kucera T, Andrisano V, Siatka T, Cahlikova L..  (2019)  Isoquinoline Alkaloids from Berberis vulgaris as Potential Lead Compounds for the Treatment of Alzheimer's Disease.,  82  (2): [PMID:30701972] [10.1021/acs.jnatprod.8b00592]
12. Plescia J, De Cesco S, Patrascu MB, Kurian J, Di Trani J, Dufresne C, Wahba AS, Janmamode N, Mittermaier AK, Moitessier N..  (2019)  Integrated Synthetic, Biophysical, and Computational Investigations of Covalent Inhibitors of Prolyl Oligopeptidase and Fibroblast Activation Protein α.,  62  (17): [PMID:31393718] [10.1021/acs.jmedchem.9b00642]
13. Plescia J, Hédou D, Pousse ME, Labarre A, Dufresne C, Mittermaier A, Moitessier N..  (2022)  Modulating the selectivity of inhibitors for prolyl oligopeptidase inhibitors and fibroblast activation protein-α for different indications.,  240  [PMID:35797897] [10.1016/j.ejmech.2022.114543]