[18F]-(2S)-2-(((3R,5S)-5-carboxy-1-((S)-4-carboxy-4-(6-(4-fluorobenzamido)hexanamido)butanoyl)pyrrolidin-3-yloxy)(hydroxy)phosphorylamino)pentanedioic acid

ID: ALA3427444

Chembl Id: CHEMBL3427444

PubChem CID: 118737818

Max Phase: Preclinical

Molecular Formula: C56H76F2N8O28P2

Molecular Weight: 704.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC[C@H](NP(=O)(O)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)CC[C@H](NC(=O)CCCCCNC(=O)c2ccc(F)cc2)C(=O)O)C1)C(=O)O.O=C(O)CC[C@H](NP(=O)(O)O[C@@H]1C[C@@H](C(=O)O)N(C(=O)CC[C@H](NC(=O)CCCCCNC(=O)c2ccc([18F])cc2)C(=O)O)C1)C(=O)O

Standard InChI:  InChI=1S/2C28H38FN4O14P/c2*29-17-7-5-16(6-8-17)25(38)30-13-3-1-2-4-22(34)31-19(26(39)40)9-11-23(35)33-15-18(14-21(33)28(43)44)47-48(45,46)32-20(27(41)42)10-12-24(36)37/h2*5-8,18-21H,1-4,9-15H2,(H,30,38)(H,31,34)(H,36,37)(H,39,40)(H,41,42)(H,43,44)(H2,32,45,46)/t2*18-,19+,20+,21+/m11/s1/i29-1;

Standard InChI Key:  QEZCNKNUGICFRG-SUOKHXJLSA-N

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: 704.60

Molecular Weight (Monoisotopic): 704.2106

AlogP: 0.54

#Rotatable Bonds: 21

Polar Surface Area: 286.27

Molecular Species: ACID

HBA: 9

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.49

CX Basic pKa: 4.16

CX LogP: -1.00

CX LogD: -16.38

Aromatic Rings: 1

Heavy Atoms: 48

QED Weighted: 0.06

Np Likeness Score: -0.25

References

1. Ley CR, Beattie NR, Dannoon S, Regan M, VanBrocklin H, Berkman CE..  (2015)  Synthesis and evaluation of constrained phosphoramidate inhibitors of prostate-specific membrane antigen.,  25  (12): [PMID:25956413] [10.1016/j.bmcl.2015.04.047]

Source

Source(1):

• Scientific Literature