{(S)-3-Methylcarbamoyl-2-[3-(3-sulfoamino-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinolin-7-yl}-sulfamic acid

ID: ALA204337

Chembl Id: CHEMBL204337

Cas Number: 875662-69-4

PubChem CID: 5327156

Max Phase: Preclinical

Molecular Formula: C20H24N4O8S2

Molecular Weight: 512.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)[C@@H]1Cc2ccc(NS(=O)(=O)O)cc2CN1C(=O)CCc1cccc(NS(=O)(=O)O)c1

Standard InChI:  InChI=1S/C20H24N4O8S2/c1-21-20(26)18-11-14-6-7-17(23-34(30,31)32)10-15(14)12-24(18)19(25)8-5-13-3-2-4-16(9-13)22-33(27,28)29/h2-4,6-7,9-10,18,22-23H,5,8,11-12H2,1H3,(H,21,26)(H,27,28,29)(H,30,31,32)/t18-/m0/s1

Standard InChI Key:  VXWOHWHCMDFHJS-SFHVURJKSA-N

Alternative Forms

1. Parent:

   

   ALA204337

   {3(S)-Methylcarbamoyl-2-[3-(3-sulfoamino-phenyl)-propionyl]-1,2,3,4-tetrahydro-isoquinolin-7-YL}-sulfamic 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: 512.57

Molecular Weight (Monoisotopic): 512.1036

AlogP: 0.75

#Rotatable Bonds: 8

Polar Surface Area: 182.21

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -1.36

CX Basic pKa:

CX LogP: -2.92

CX LogD: -5.20

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.32

Np Likeness Score: -0.73

References

1. Klopfenstein SR, Evdokimov AG, Colson AO, Fairweather NT, Neuman JJ, Maier MB, Gray JL, Gerwe GS, Stake GE, Howard BW, Farmer JA, Pokross ME, Downs TR, Kasibhatla B, Peters KG..  (2006)  1,2,3,4-Tetrahydroisoquinolinyl sulfamic acids as phosphatase PTP1B inhibitors.,  16  (6): [PMID:16386905] [10.1016/j.bmcl.2005.12.051]

2. Combs AP..  (2010)  Recent advances in the discovery of competitive protein tyrosine phosphatase 1B inhibitors for the treatment of diabetes, obesity, and cancer.,  53  (6): [PMID:20000419] [10.1021/jm901090b]

Source

Source(1):

• Scientific Literature