N-[5-({3-[5-(Acetyl-hydroxy-amino)-pentylcarbamoyl]-propionyl}-hydroxy-amino)-pentyl]-N'-{5-[(adamantane-1-carbonyl)-amino]-pentyl}-N'-hydroxy-succinamide

ID: ALA592000

Chembl Id: CHEMBL592000

PubChem CID: 42599400

Max Phase: Preclinical

Molecular Formula: C36H62N6O9

Molecular Weight: 722.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)C12CC3CC(CC(C3)C1)C2

Standard InChI:  InChI=1S/C36H62N6O9/c1-27(43)40(49)18-8-2-5-15-37-31(44)11-13-33(46)41(50)19-9-3-6-16-38-32(45)12-14-34(47)42(51)20-10-4-7-17-39-35(48)36-24-28-21-29(25-36)23-30(22-28)26-36/h28-30,49-51H,2-26H2,1H3,(H,37,44)(H,38,45)(H,39,48)

Standard InChI Key:  JKDZVYIETMKGIY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA592000

   N-[5-[acetyl(hydroxy)amino]pentyl]-N'-[5-[[4-[5-(adamantane-1-carbonylamino)pentyl-hydroxyamino]-4-oxobutanoyl]amino]pentyl]-N'-hydroxybutanediamide

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: 722.93

Molecular Weight (Monoisotopic): 722.4578

AlogP: 3.30

#Rotatable Bonds: 25

Polar Surface Area: 208.92

Molecular Species: NEUTRAL

HBA: 9

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.92

CX Basic pKa: 0.48

CX LogP: 0.40

CX LogD: 0.28

Aromatic Rings: ┄

Heavy Atoms: 51

QED Weighted: 0.05

Np Likeness Score: -0.12

References

1. Liu J, Obando D, Schipanski LG, Groebler LK, Witting PK, Kalinowski DS, Richardson DR, Codd R..  (2010)  Conjugates of desferrioxamine B (DFOB) with derivatives of adamantane or with orally available chelators as potential agents for treating iron overload.,  53  (3): [PMID:20041672] [10.1021/jm9016703]

2. Telfer TJ, Liddell JR, Duncan C, White AR, Codd R..  (2017)  Adamantyl- and other polycyclic cage-based conjugates of desferrioxamine B (DFOB) for treating iron-mediated toxicity in cell models of Parkinson's disease.,  27  (8): [PMID:28285915] [10.1016/j.bmcl.2017.03.001]

Source

Source(1):

• Scientific Literature