ID: ALA3359672

Max Phase: Preclinical

Molecular Formula: C14H20N2O4

Molecular Weight: 280.32

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1ccc(C/N=C2\N[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C14H20N2O4/c1-8-2-4-9(5-3-8)6-15-14-13(20)12(19)11(18)10(7-17)16-14/h2-5,10-13,17-20H,6-7H2,1H3,(H,15,16)/t10-,11+,12+,13-/m1/s1

Standard InChI Key:  QGRRHVRVRHDODY-MROQNXINSA-N

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

Properties

Molecular Weight: 280.32

Molecular Weight (Monoisotopic): 280.1423

AlogP: -1.06

#Rotatable Bonds: 3

Polar Surface Area: 105.31

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.52

CX Basic pKa: 7.30

CX LogP: -0.89

CX LogD: -1.14

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.49

Np Likeness Score: 0.58

References

1. Fan QH, Claunch KA, Striegler S..  (2014)  Structure-activity relationship of highly potent galactonoamidine inhibitors toward β-galactosidase (Aspergillus oryzae).,  57  (21): [PMID:25295392] [10.1021/jm501111y]

2. Fan QH, Pickens JB, Striegler S, Gervaise CD..  (2016)  Illuminating the binding interactions of galactonoamidines during the inhibition of β-galactosidase (E. coli).,  24  (4): [PMID:26740154] [10.1016/j.bmc.2015.12.034]

3. Pickens JB, Striegler S, Fan QH..  (2016)  Arabinoamidine synthesis and its inhibition toward β-glucosidase (sweet almonds) in comparison to a library of galactonoamidines.,  24  (16): [PMID:27298003] [10.1016/j.bmc.2016.04.069]

4. Pickens JB, Wang F, Striegler S..  (2017)  Picomolar inhibition of β-galactosidase (bovine liver) attributed to loop closure.,  25  (20): [PMID:28844803] [10.1016/j.bmc.2017.07.020]

Source

Source(1):

• Scientific Literature