(3R,4R,5S)-4-Acetylamino-3-sec-butoxy-5-guanidino-cyclohex-1-enecarboxylic acid

ID: ALA2114178

Chembl Id: CHEMBL2114178

PubChem CID: 493875

Max Phase: Preclinical

Molecular Formula: C14H24N4O4

Molecular Weight: 312.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@H](C)O[C@@H]1C=C(C(=O)O)C[C@H](NC(=N)N)[C@H]1NC(C)=O

Standard InChI:  InChI=1S/C14H24N4O4/c1-4-7(2)22-11-6-9(13(20)21)5-10(18-14(15)16)12(11)17-8(3)19/h6-7,10-12H,4-5H2,1-3H3,(H,17,19)(H,20,21)(H4,15,16,18)/t7-,10+,11-,12-/m1/s1

Standard InChI Key:  BKSBSWKRQZCHQR-UYZPKGHCSA-N

Alternative Forms

1. Parent:

   

   ALA2114178

   (3R,4R,5S)-4-Acetylamino-3-((R)-sec-butoxy)-5-guanidino-cyclohex-1-enecarboxylic acid

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: 312.37

Molecular Weight (Monoisotopic): 312.1798

AlogP: -0.06

#Rotatable Bonds: 6

Polar Surface Area: 137.53

Molecular Species: ZWITTERION

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.05

CX Basic pKa: 11.96

CX LogP: -2.07

CX LogD: -2.07

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.34

Np Likeness Score: 0.90

References

1. Kim CU, Lew W, Williams MA, Wu H, Zhang L, Chen X, Escarpe PA, Mendel DB, Laver WG, Stevens RC..  (1998)  Structure-activity relationship studies of novel carbocyclic influenza neuraminidase inhibitors.,  41  (14): [PMID:9651151] [10.1021/jm980162u]

2. Kim CU, Lew W, Williams MA, Wu H, Zhang L, Chen X, Escarpe PA, Mendel DB, Laver WG, Stevens RC..  (1998)  Structure-activity relationship studies of novel carbocyclic influenza neuraminidase inhibitors.,  41  (14): [PMID:9651151] [10.1021/jm980162u]

3. Murumkar PR, Le L, Truong TN, Yadav MR.  (2011)  Determination of structural requirements of influenza neuraminidase type A inhibitors and binding interaction analysis with the active site of A/H1N1 by 3D-QSAR CoMFA and CoMSIA modeling,  2  (8): [10.1039/C1MD00050K]

4. Wang Z, Cheng LP, Zhang XH, Pang W, Li L, Zhao JL..  (2017)  Design, synthesis and biological evaluation of novel oseltamivir derivatives as potent neuraminidase inhibitors.,  27  (24): [PMID:29141777] [10.1016/j.bmcl.2017.11.003]

Source

Source(1):

• Scientific Literature