(S)-2-Amino-5-[N'-(2-methoxy-ethyl)-guanidino]-pentanoic acid

ID: ALA366222

PubChem CID: 11413609

Max Phase: Preclinical

Molecular Formula: C9H20N4O3

Molecular Weight: 232.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCCNC(=N)NCCC[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C9H20N4O3/c1-16-6-5-13-9(11)12-4-2-3-7(10)8(14)15/h7H,2-6,10H2,1H3,(H,14,15)(H3,11,12,13)/t7-/m0/s1

Standard InChI Key:  XMBSMMCPKFDGEO-ZETCQYMHSA-N

Molfile:  

     RDKit          2D

 16 15  0  0  1  0  0  0  0  0999 V2000
    0.2606    0.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5000    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5000    1.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7999    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0999    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3999    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6999    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9999    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9999   -1.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2999    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3393    0.1503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2999    1.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  2  0
 14 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA366222

   N~5~-{imino[(2-Methoxyethyl)amino]methyl}-L-Ornithine

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: 232.28

Molecular Weight (Monoisotopic): 232.1535

AlogP: -1.06

#Rotatable Bonds: 8

Polar Surface Area: 120.46

Molecular Species: ZWITTERION

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.29

CX Basic pKa: 12.39

CX LogP: -2.93

CX LogD: -4.62

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.21

Np Likeness Score: 0.33

References

1. Rossiter S, Smith CL, Malaki M, Nandi M, Gill H, Leiper JM, Vallance P, Selwood DL..  (2005)  Selective substrate-based inhibitors of mammalian dimethylarginine dimethylaminohydrolase.,  48  (14): [PMID:16000003] [10.1021/jm050187a]

2. Kotthaus J, Schade D, Muschick N, Beitz E, Clement B..  (2008)  Structure-activity relationship of novel and known inhibitors of human dimethylarginine dimethylaminohydrolase-1: alkenyl-amidines as new leads.,  16  (24): [PMID:19013076] [10.1016/j.bmc.2008.10.058]

3.  (2014)  Inhibitors of dimethylarginine dimethylaminohydrolase, 

4.  (2014)  Dimethylarginine Dimethylaminohydrolase inhibitors and methods of use thereof, 

5. Lunk I, Litty FA, Hennig S, Vetter IR, Kotthaus J, Altmann KS, Ott G, Havemeyer A, Carrillo García C, Clement B, Schade D..  (2020)  Discovery of N-(4-Aminobutyl)-N'-(2-methoxyethyl)guanidine as the First Selective, Nonamino Acid, Catalytic Site Inhibitor of Human Dimethylarginine Dimethylaminohydrolase-1 (hDDAH-1).,  63  (1): [PMID:31841335] [10.1021/acs.jmedchem.9b01230]

Source

Source(3):

• Scientific Literature
• BindingDB Database
• Patent Bioactivity Data