6-Amino-2-[(9-mercaptomethyl-10-oxo-azecane-2-carbonyl)-amino]-hexanoic acid hydrochloride

ID: ALA555862

PubChem CID: 44349893

Max Phase: Preclinical

Molecular Formula: C17H32ClN3O4S

Molecular Weight: 373.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.NCCCC[C@@H](NC(=O)C1CCCCCCC(CS)C(=O)N1)C(=O)O

Standard InChI:  InChI=1S/C17H31N3O4S.ClH/c18-10-6-5-9-14(17(23)24)20-16(22)13-8-4-2-1-3-7-12(11-25)15(21)19-13;/h12-14,25H,1-11,18H2,(H,19,21)(H,20,22)(H,23,24);1H/t12?,13?,14-;/m1./s1

Standard InChI Key:  UWCHZBLBKKUVFU-YLIRPONSSA-N

Molfile:  

     RDKit          2D

 26 25  0  0  0  0  0  0  0  0999 V2000
    7.7125   -2.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -1.8000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -2.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -3.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -2.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -1.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -3.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2375   -3.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875   -2.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -2.9917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -3.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125   -4.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -1.7917    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -3.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -1.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -3.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7542   -4.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2667   -4.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7292   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  6  1  0
  5  4  1  0
  6  2  1  0
  7  3  1  0
  9  8  1  6
  9  5  1  0
 10  3  2  0
 11  4  2  0
 12  8  2  0
 13  8  1  0
 14 15  1  0
 15  7  1  0
 16 20  1  0
 17  7  1  0
 18  6  1  0
 19  9  1  0
 20 22  1  0
 21 19  1  0
 22 21  1  0
 23 17  1  0
 24 18  1  0
 25 24  1  0
 26 25  1  0
 23 26  1  0
M  END

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: 373.52

Molecular Weight (Monoisotopic): 373.2035

AlogP: 1.07

#Rotatable Bonds: 8

Polar Surface Area: 121.52

Molecular Species: ZWITTERION

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.83

CX Basic pKa: 10.44

CX LogP: -1.08

CX LogD: -1.09

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.32

Np Likeness Score: 0.48

References

1. MacPherson LJ, Bayburt EK, Capparelli MP, Bohacek RS, Clarke FH, Ghai RD, Sakane Y, Berry CJ, Peppard JV, Trapani AJ..  (1993)  Design and synthesis of an orally active macrocyclic neutral endopeptidase 24.11 inhibitor.,  36  (24): [PMID:8254611] [10.1021/jm00076a009]

Source

Source(1):

• Scientific Literature