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

ID: ALA592637

Chembl Id: CHEMBL592637

PubChem CID: 46231196

Max Phase: Preclinical

Molecular Formula: C38H66N6O9

Molecular Weight: 750.98

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(C)(CC(C)(C3)C1)C2

Standard InChI:  InChI=1S/C38H66N6O9/c1-29(45)42(51)20-10-4-7-17-39-31(46)13-15-33(48)43(52)21-11-5-8-18-40-32(47)14-16-34(49)44(53)22-12-6-9-19-41-35(50)38-25-30-23-36(2,27-38)26-37(3,24-30)28-38/h30,51-53H,4-28H2,1-3H3,(H,39,46)(H,40,47)(H,41,50)

Standard InChI Key:  MFAUREOOURUGSY-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA592637

   N-[5-[acetyl(hydroxy)amino]pentyl]-N'-[5-[[4-[5-[(3,5-dimethyladamantane-1-carbonyl)amino]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: 750.98

Molecular Weight (Monoisotopic): 750.4891

AlogP: 4.08

#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: 0.98

CX LogP: 1.00

CX LogD: 0.88

Aromatic Rings: ┄

Heavy Atoms: 53

QED Weighted: 0.05

Np Likeness Score: -0.07

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