(S)-4-(3-chloro-4-methoxybenzylamino)-2-(2-(hydroxymethyl)pyrrolidin-1-yl)-N-(3-hydroxypropyl)pyrimidine-5-carboxamide

ID: ALA3352836

Chembl Id: CHEMBL3352836

PubChem CID: 118720075

Max Phase: Preclinical

Molecular Formula: C21H28ClN5O4

Molecular Weight: 449.94

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1ccc(CNc2nc(N3CCC[C@H]3CO)ncc2C(=O)NCCCO)cc1Cl

Standard InChI:  InChI=1S/C21H28ClN5O4/c1-31-18-6-5-14(10-17(18)22)11-24-19-16(20(30)23-7-3-9-28)12-25-21(26-19)27-8-2-4-15(27)13-29/h5-6,10,12,15,28-29H,2-4,7-9,11,13H2,1H3,(H,23,30)(H,24,25,26)/t15-/m0/s1

Standard InChI Key:  RECLIWYSXXJJLO-HNNXBMFYSA-N

Alternative Forms

  1. Parent:

    ALA3352836

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Associated Targets(Human)

PDE5A Tclin Phosphodiesterase 5A (5113 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

PDE5A Phosphodiesterase 5A (190 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Corpus cavernosum (62 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 449.94Molecular Weight (Monoisotopic): 449.1830AlogP: 1.82#Rotatable Bonds: 10
Polar Surface Area: 119.84Molecular Species: NEUTRALHBA: 8HBD: 4
#RO5 Violations: HBA (Lipinski): 9HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 13.98CX Basic pKa: 5.55CX LogP: 1.94CX LogD: 1.94
Aromatic Rings: 2Heavy Atoms: 31QED Weighted: 0.41Np Likeness Score: -1.06

References

1. Sakamoto T, Koga Y, Hikota M, Matsuki K, Murakami M, Kikkawa K, Fujishige K, Kotera J, Omori K, Morimoto H, Yamada K..  (2014)  The discovery of avanafil for the treatment of erectile dysfunction: a novel pyrimidine-5-carboxamide derivative as a potent and highly selective phosphodiesterase 5 inhibitor.,  24  (23): [PMID:25455484] [10.1016/j.bmcl.2014.10.008]
2. Shaaban MA,Elshaier YAMM,Hammad AH,Farag NA,Hassan Haredy H,AbdEl-Ghany AA,Mohamed KO.  (2020)  Design and synthesis of pyrazolo[3,4-d]pyrimidinone derivatives: Discovery of selective phosphodiesterase-5 inhibitors.,  30  (16): [PMID:32631538] [10.1016/j.bmcl.2020.127337]

Source