(S)-2-[3-((S)-3-Carboxy-1-carboxy-propyl)-ureido]-pentanedioic acid

ID: ALA46005

Chembl Id: CHEMBL46005

Cas Number: 302941-52-2

PubChem CID: 9797132

Max Phase: Preclinical

Molecular Formula: C11H16N2O9

Molecular Weight: 320.25

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (2S,2'S)-2,2'-Carbonylbis(Azanediyl)Dipentanedioic Acid | DUPA|302941-52-2|CHEMBL46005|N,N'-Carbonylbis[L-glutamicacid]|(2S,2'S)-2,2'-(Carbonylbis(azanediyl))diglutaric acid|(2S,2'S)-2,2'-Carbonylbis(Azanediyl)Dipentanedioic Acid|SCHEMBL12145776|N,N'-Carbonylbis[L-glutamic Acid]|SWN41522|(2S)-2-[[(1S)-1,3-dicarboxypropyl]carbamoylamino]pentanedioic Acid|BDBM50102258|AKOS037653350|HY-111606|CS-0088442|2-[3-(1,3-Dicarboxy-propyl)-ureido]-pentanedioic acid|(2S,2'S)-2,2'-(Carbonylbis(azanediyl))dipeShow More⌵

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

Standard InChI:  InChI=1S/C11H16N2O9/c14-7(15)3-1-5(9(18)19)12-11(22)13-6(10(20)21)2-4-8(16)17/h5-6H,1-4H2,(H,14,15)(H,16,17)(H,18,19)(H,20,21)(H2,12,13,22)/t5-,6-/m0/s1

Standard InChI Key:  SOAPXKSPJAZNGO-WDSKDSINSA-N

Alternative Forms

1. Parent:

   

   ALA46005

   (2S,2'S)-2,2'-Carbonylbis(Azanediyl)Dipentanedioic 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: 320.25

Molecular Weight (Monoisotopic): 320.0856

AlogP: -1.08

#Rotatable Bonds: 10

Polar Surface Area: 190.33

Molecular Species: ACID

HBA: 5

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.86

CX Basic pKa: ┄

CX LogP: -1.53

CX LogD: -14.63

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.29

Np Likeness Score: 0.04

References

1. Kozikowski AP, Zhang J, Nan F, Petukhov PA, Grajkowska E, Wroblewski JT, Yamamoto T, Bzdega T, Wroblewska B, Neale JH..  (2004)  Synthesis of urea-based inhibitors as active site probes of glutamate carboxypeptidase II: efficacy as analgesic agents.,  47  (7): [PMID:15027864] [10.1021/jm0306226]

2. Kozikowski AP, Nan F, Conti P, Zhang J, Ramadan E, Bzdega T, Wroblewska B, Neale JH, Pshenichkin S, Wroblewski JT..  (2001)  Design of remarkably simple, yet potent urea-based inhibitors of glutamate carboxypeptidase II (NAALADase).,  44  (3): [PMID:11462970] [10.1021/jm000406m]

3. Graham K, Lesche R, Gromov AV, Böhnke N, Schäfer M, Hassfeld J, Dinkelborg L, Kettschau G..  (2012)  Radiofluorinated derivatives of 2-(phosphonomethyl)pentanedioic acid as inhibitors of prostate specific membrane antigen (PSMA) for the imaging of prostate cancer.,  55  (22): [PMID:23025786] [10.1021/jm300710j]

4. Roy J, Nguyen TX, Kanduluru AK, Venkatesh C, Lv W, Reddy PV, Low PS, Cushman M..  (2015)  DUPA conjugation of a cytotoxic indenoisoquinoline topoisomerase I inhibitor for selective prostate cancer cell targeting.,  58  (7): [PMID:25822623] [10.1021/jm5018384]

5. Young JD, Ma MT, Eykyn TR, Atkinson RA, Abbate V, Cilibrizzi A, Hider RC, Blower PJ..  (2021)  Dipeptide inhibitors of the prostate specific membrane antigen (PSMA): A comparison of urea and thiourea derivatives.,  42  [PMID:33865971] [10.1016/j.bmcl.2021.128044]

Source

Source(1):

• Scientific Literature