(S)-2-(3-((S)-5-Amino-1-carboxypentyl)ureido)pentanedioic Acid

ID: ALA458202

Chembl Id: CHEMBL458202

Cas Number: 1025796-32-0

PubChem CID: 24952014

Max Phase: Preclinical

Molecular Formula: C12H21N3O7

Molecular Weight: 319.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCCC[C@H](NC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O

Standard InChI:  InChI=1S/C12H21N3O7/c13-6-2-1-3-7(10(18)19)14-12(22)15-8(11(20)21)4-5-9(16)17/h7-8H,1-6,13H2,(H,16,17)(H,18,19)(H,20,21)(H2,14,15,22)/t7-,8-/m0/s1

Standard InChI Key:  ZZASEPMMGWJWOV-YUMQZZPRSA-N

Alternative Forms

1. Parent:

   

   ALA458202

   (S)-2-(3-((S)-5-Amino-1-carboxypentyl)ureido)pentanedioic Acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 319.31

Molecular Weight (Monoisotopic): 319.1380

AlogP: -0.81

#Rotatable Bonds: 11

Polar Surface Area: 179.05

Molecular Species: ZWITTERION

HBA: 5

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.05

CX Basic pKa: 10.21

CX LogP: -3.85

CX LogD: -10.15

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.27

Np Likeness Score: 0.29

References

1. Maresca KP, Hillier SM, Femia FJ, Keith D, Barone C, Joyal JL, Zimmerman CN, Kozikowski AP, Barrett JA, Eckelman WC, Babich JW..  (2009)  A series of halogenated heterodimeric inhibitors of prostate specific membrane antigen (PSMA) as radiolabeled probes for targeting prostate cancer.,  52  (2): [PMID:19111054] [10.1021/jm800994j]

2. Tykvart J, Schimer J, Bařinková J, Pachl P, Poštová-Slavětínská L, Majer P, Konvalinka J, Šácha P..  (2014)  Rational design of urea-based glutamate carboxypeptidase II (GCPII) inhibitors as versatile tools for specific drug targeting and delivery.,  22  (15): [PMID:24954515] [10.1016/j.bmc.2014.05.061]

3. Machulkin AE, Skvortsov DA, Ivanenkov YA, Ber AP, Kavalchuk MV, Aladinskaya AV, Uspenskaya AA, Shafikov RR, Plotnikova EA, Yakubovskaya RI, Nimenko EA, Zyk NU, Beloglazkina EK, Zyk NV, Koteliansky VE, Majouga AG..  (2019)  Synthesis and biological evaluation of PSMA-targeting paclitaxel conjugates.,  29  (16): [PMID:31248772] [10.1016/j.bmcl.2019.06.035]

4. Machulkin AE, Shafikov RR, Uspenskaya AA, Petrov SA, Ber AP, Skvortsov DA, Nimenko EA, Zyk NU, Smirnova GB, Pokrovsky VS, Abakumov MA, Saltykova IV, Akhmirov RT, Garanina AS, Polshakov VI, Saveliev OY, Ivanenkov YA, Aladinskaya AV, Finko AV, Yamansarov EU, Krasnovskaya OO, Erofeev AS, Gorelkin PV, Dontsova OA, Beloglazkina EK, Zyk NV, Khazanova ES, Majouga AG..  (2021)  Synthesis and Biological Evaluation of PSMA Ligands with Aromatic Residues and Fluorescent Conjugates Based on Them.,  64  (8.0): [PMID:33822606] [10.1021/acs.jmedchem.0c01935]

5. Zyk NY, Ber AP, Nimenko EA, Shafikov RR, Evteev SA, Petrov SA, Uspenskaya AA, Dashkova NS, Ivanenkov YA, Skvortsov DA, Beloglazkina EK, Majouga AG, Machulkin AE..  (2022)  Synthesis and initial in vitro evaluation of PSMA-targeting ligands with a modified aromatic moiety at the lysine ε-nitrogen atom.,  71  [PMID:35661685] [10.1016/j.bmcl.2022.128840]

6. Machulkin AE, Uspenskaya AA, Zyk NY, Nimenko EA, Ber AP, Petrov SA, Shafikov RR, Skvortsov DA, Smirnova GB, Borisova YA, Pokrovsky VS, Kolmogorov VS, Vaneev AN, Ivanenkov YA, Khudyakov AD, Kovalev SV, Erofeev AS, Gorelkin PV, Beloglazkina EK, Zyk NV, Khazanova ES, Majouga AG..  (2022)  PSMA-targeted small-molecule docetaxel conjugate: Synthesis and preclinical evaluation.,  227  [PMID:34717125] [10.1016/j.ejmech.2021.113936]

Source

Source(1):

• Scientific Literature