8-Amino-1,3-bis-cyclopropylmethyl-3,7-dihydro-purine-2,6-dione

ID: ALA356323

Chembl Id: CHEMBL356323

Cas Number: 132210-43-6

PubChem CID: 71356

Max Phase: Phase

Molecular Formula: C13H17N5O2

Molecular Weight: 275.31

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BRL 61063 | BRL-61063 | Cipamfylline|132210-43-6|BRL-61063|8-amino-1,3-bis(cyclopropylmethyl)-7H-purine-2,6-dione|AFP56R140L|CHEMBL356323|8-Amino-1,3-bis(cyclopropylmethyl)xanthine|Brl 61063|BRL61063|1H-Purine-2,6-dione, 8-amino-1,3-bis(cyclopropylmethyl)-3,7-dihydro-|Cipamfylline [USAN]|Cipamfylline [USAN:INN]|UNII-AFP56R140L|Cipamfyllinum|Cipamfylline (USAN/INN)|CIPAMFYLLINE [INN]|SCHEMBL26990|MLS006010682|SCHEMBL8327157|Cipamfylline, >=98% (HPLC)|DTXSID50157437|CHEBI:177777|KSPYMJJKQMWWNB-UHFShow More⌵

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

Alternative Forms

1. Parent:

   

   ALA356323

   CIPAMFYLLINE

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

Calculated 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