ID: ALA356323

Max Phase: Phase

Molecular Formula: C13H17N5O2

Molecular Weight: 275.31

Molecule Type: Small molecule

Representations

Synonyms (2): BRL 61063 | BRL-61063
Synonyms from Alternative Forms(2):

Canonical SMILES:  Nc1nc2c([nH]1)c(=O)n(CC1CC1)c(=O)n2CC1CC1

Standard InChI:  InChI=1S/C13H17N5O2/c14-12-15-9-10(16-12)17(5-7-1-2-7)13(20)18(11(9)19)6-8-3-4-8/h7-8H,1-6H2,(H3,14,15,16)

Standard InChI Key:  KSPYMJJKQMWWNB-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 275.31

Molecular Weight (Monoisotopic): 275.1382

AlogP: 0.29

#Rotatable Bonds: 4

Polar Surface Area: 98.70

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.25

CX Basic pKa: 1.40

CX LogP: 0.65

CX LogD: 0.60

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.84

Np Likeness Score: -0.55

References

1. Buckle DR, Arch JR, Connolly BJ, Fenwick AE, Foster KA, Murray KJ, Readshaw SA, Smallridge M, Smith DG..  (1994)  Inhibition of cyclic nucleotide phosphodiesterase by derivatives of 1,3-bis(cyclopropylmethyl)xanthine.,  37  (4): [PMID:8120866] [10.1021/jm00030a007]

2. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

3. Day JP, Lindsay B, Riddell T, Jiang Z, Allcock RW, Abraham A, Sookup S, Christian F, Bogum J, Martin EK, Rae RL, Anthony D, Rosair GM, Houslay DM, Huston E, Baillie GS, Klussmann E, Houslay MD, Adams DR..  (2011)  Elucidation of a structural basis for the inhibitor-driven, p62 (SQSTM1)-dependent intracellular redistribution of cAMP phosphodiesterase-4A4 (PDE4A4).,  54  (9): [PMID:21456625] [10.1021/jm200070e]

4. Felding J, Sørensen MD, Poulsen TD, Larsen J, Andersson C, Refer P, Engell K, Ladefoged LG, Thormann T, Vinggaard AM, Hegardt P, Søhoel A, Nielsen SF..  (2014)  Discovery and early clinical development of 2-{6-[2-(3,5-dichloro-4-pyridyl)acetyl]-2,3-dimethoxyphenoxy}-N-propylacetamide (LEO 29102), a soft-drug inhibitor of phosphodiesterase 4 for topical treatment of atopic dermatitis.,  57  (14): [PMID:24984230] [10.1021/jm500378a]

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names