(S)-5-(4-benzyloxyphenyl)-4-[(7-phenylheptanoyl)amino]pentanoic acid

ID: ALA1084102

Cas Number: 393569-31-8

PubChem CID: 446400

Product Number: S339610, Order Now?

Max Phase: Preclinical

Molecular Formula: C31H37NO4

Molecular Weight: 487.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC[C@@H](Cc1ccc(OCc2ccccc2)cc1)NC(=O)CCCCCCc1ccccc1

Standard InChI:  InChI=1S/C31H37NO4/c33-30(16-10-2-1-5-11-25-12-6-3-7-13-25)32-28(19-22-31(34)35)23-26-17-20-29(21-18-26)36-24-27-14-8-4-9-15-27/h3-4,6-9,12-15,17-18,20-21,28H,1-2,5,10-11,16,19,22-24H2,(H,32,33)(H,34,35)/t28-/m0/s1

Standard InChI Key:  KWLUIYFCMHKLKY-NDEPHWFRSA-N

Molfile:  

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 36 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1084102

   sPLA2 inhibitor

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: 487.64

Molecular Weight (Monoisotopic): 487.2723

AlogP: 6.35

#Rotatable Bonds: 16

Polar Surface Area: 75.63

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.26

CX Basic pKa: ┄

CX LogP: 6.89

CX LogD: 3.90

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.23

Np Likeness Score: -0.04

References

1. Drews A, Bovens S, Roebrock K, Sunderkötter C, Reinhardt D, Schäfers M, van der Velde A, Schulze Elfringhoff A, Fabian J, Lehr M..  (2010)  1-(5-carboxyindol-1-yl)propan-2-one inhibitors of human cytosolic phospholipase A(2)alpha with reduced lipophilicity: synthesis, biological activity, metabolic stability, solubility, bioavailability, and topical in vivo activity.,  53  (14): [PMID:20583844] [10.1021/jm1001088]

2. Bovens S, Schulze Elfringhoff A, Kaptur M, Reinhardt D, Schäfers M, Lehr M..  (2010)  1-(5-Carboxyindol-1-yl)propan-2-one inhibitors of human cytosolic phospholipase A2α: effect of substituents in position 3 of the indole scaffold on inhibitory potency, metabolic stability, solubility, and bioavailability.,  53  (23): [PMID:21067218] [10.1021/jm101094p]

3. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

4. Vasilakaki S, Barbayianni E, Magrioti V, Pastukhov O, Constantinou-Kokotou V, Huwiler A, Kokotos G..  (2016)  Inhibitors of secreted phospholipase A2 suppress the release of PGE2 in renal mesangial cells.,  24  (13): [PMID:27234891] [10.1016/j.bmc.2016.05.017]

5. Starkus JG, Poerzgen P, Layugan K, Kawabata KG, Goto JI, Suzuki S, Myers G, Kelly M, Penner R, Fleig A, Horgen FD..  (2017)  Scalaradial Is a Potent Inhibitor of Transient Receptor Potential Melastatin 2 (TRPM2) Ion Channels.,  80  (10): [PMID:29019677] [10.1021/acs.jnatprod.7b00515]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data