(R)-2-((S)-1-amino-3-(1H-indol-3-yl)-1-oxopropan-2-ylcarbamoyl)-4-methylpentyl((R)-1-amino-3-phenylpropyl)phosphinic acid

ID: ALA4863168

PubChem CID: 164625468

Max Phase: Preclinical

Molecular Formula: C27H37N4O4P

Molecular Weight: 512.59

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)C[C@@H](CP(=O)(O)[C@@H](N)CCc1ccccc1)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(N)=O

Standard InChI:  InChI=1S/C27H37N4O4P/c1-18(2)14-21(17-36(34,35)25(28)13-12-19-8-4-3-5-9-19)27(33)31-24(26(29)32)15-20-16-30-23-11-7-6-10-22(20)23/h3-11,16,18,21,24-25,30H,12-15,17,28H2,1-2H3,(H2,29,32)(H,31,33)(H,34,35)/t21-,24-,25+/m0/s1

Standard InChI Key:  QKFOTLXPIIESQI-GVXSCFBNSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4863168

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 512.59

Molecular Weight (Monoisotopic): 512.2552

AlogP: 3.53

#Rotatable Bonds: 13

Polar Surface Area: 151.30

Molecular Species: ZWITTERION

HBA: 4

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.65

CX Basic pKa: 9.61

CX LogP: 1.77

CX LogD: 1.77

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.22

Np Likeness Score: 0.10

References

1. Wilding B, Pasqua AE, E A Chessum N, Pierrat OA, Hahner T, Tomlin K, Shehu E, Burke R, Richards GM, Whitton B, Arwert EN, Thapaliya A, Salimraj R, van Montfort R, Skawinska A, Hayes A, Raynaud F, Chopra R, Jones K, Newton G, Cheeseman MD..  (2021)  Investigating the phosphinic acid tripeptide mimetic DG013A as a tool compound inhibitor of the M1-aminopeptidase ERAP1.,  42  [PMID:33887439] [10.1016/j.bmcl.2021.128050]

2. Chen, H H, Noble, F F, Roques, B P BP and Fournié-Zaluski, M C MC.  2001-10-11  Long lasting antinociceptive properties of enkephalin degrading enzyme (NEP and APN) inhibitor prodrugs.  [PMID:11585456]

3. Vassiliou, Stamatia S and 7 more authors.  2014-10-09  Structure-guided, single-point modifications in the phosphinic dipeptide structure yield highly potent and selective inhibitors of neutral aminopeptidases.  [PMID:25192493]

4. Węglarz-Tomczak, Ewelina and 5 more authors.  2016-07-19  A structural insight into the P1S1 binding mode of diaminoethylphosphonic and phosphinic acids, selective inhibitors of alanine aminopeptidases.  [PMID:27100031]

5. Singh, Rohit R, Williams, Jessica J and Vince, Robert R.  2017-10-20  Puromycin based inhibitors of aminopeptidases for the potential treatment of hematologic malignancies.  [PMID:28803047]

6. Pascual, Isel and 10 more authors.  2017-11  Discovery of novel non-competitive inhibitors of mammalian neutral M1 aminopeptidase (APN).  [PMID:28964831]

Source

Source(1):

• Scientific Literature