N-[(1R,3R)-3-(2,3-Dihydro-benzofuran-4-yl)-2,2-dimethyl-cyclopropanecarbonyl]-guanidine

ID: ALA51879

Chembl Id: CHEMBL51879

Cas Number: 230640-88-7

PubChem CID: 9925502

Max Phase: Preclinical

Molecular Formula: C15H19N3O2

Molecular Weight: 273.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BMS-284640 | BMS-284640|230640-88-7|Cyclopropanecarboxamide, N-(aminoiminomethyl)-3-(2,3-dihydro-4-benzofuranyl)-2,2-dimethyl-, (1R,3R)-|UNII-XP87V064PV|XP87V064PV|(+)-BMS-284640|CHEMBL51879|(1R,3R)-N-(diaminomethylidene)-3-(2,3-dihydro-1-benzofuran-4-yl)-2,2-dimethylcyclopropane-1-carboxamide|SCHEMBL13285838|BDBM50104844|AKOS040750850|Q27293948|N-[(1R,3R)-3-(2,3-Dihydro-benzofuran-4-yl)-2,2-dimethyl-cyclopropanecarbonyl]-guanidine|(1r,3r)-N-(diaminomethylene)-3-(2,3-dihydro-1-benzofuran-4-yl)-2Show More⌵

Canonical SMILES:  CC1(C)[C@H](C(=O)N=C(N)N)[C@H]1c1cccc2c1CCO2

Standard InChI:  InChI=1S/C15H19N3O2/c1-15(2)11(12(15)13(19)18-14(16)17)9-4-3-5-10-8(9)6-7-20-10/h3-5,11-12H,6-7H2,1-2H3,(H4,16,17,18,19)/t11-,12+/m1/s1

Standard InChI Key:  BSKQEHDSFIRYHK-NEPJUHHUSA-N

Alternative Forms

1. Parent:

   

   ALA51879

   Cyclopropanecarboxamide, N-(aminoiminomethyl)-3-(2,3-dihydro-4-benzofuranyl)-2,2-dimethyl-, (1R,3R)-

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: 273.34

Molecular Weight (Monoisotopic): 273.1477

AlogP: 1.16

#Rotatable Bonds: 2

Polar Surface Area: 90.70

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.63

CX LogP: 0.97

CX LogD: -0.21

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.62

Np Likeness Score: 0.23

References

1. Ahmad S, Ngu K, Combs DW, Wu SC, Weinstein DS, Liu W, Chen BC, Chandrasena G, Dorso CR, Kirby M, Atwal KS..  (2004)  Aminoimidazoles as bioisosteres of acylguanidines: novel, potent, selective and orally bioavailable inhibitors of the sodium hydrogen exchanger isoform-1.,  14  (1): [PMID:14684323] [10.1016/j.bmcl.2003.09.066]

2. Ahmad S, Doweyko LM, Dugar S, Grazier N, Ngu K, Wu SC, Yost KJ, Chen BC, Gougoutas JZ, DiMarco JD, Lan SJ, Gavin BJ, Chen AY, Dorso CR, Serafino R, Kirby M, Atwal KS..  (2001)  Arylcyclopropanecarboxyl guanidines as novel, potent, and selective inhibitors of the sodium hydrogen exchanger isoform-1.,  44  (20): [PMID:11563929] [10.1021/jm010100v]

3.  (2014)  NHE3-binding compounds and methods for inhibiting phosphate transport, 

4.  (2013)  Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders, 

5. Talele TT..  (2018)  Natural-Products-Inspired Use of the gem-Dimethyl Group in Medicinal Chemistry.,  61  (6): [PMID:28850227] [10.1021/acs.jmedchem.7b00315]

6.  (2016)  Nhe3-binding compounds and methods for inhibiting phosphate transport, 

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data