ID: ALA2170080

Max Phase: Preclinical

Molecular Formula: C18H23N2O7PS

Molecular Weight: 442.43

Molecule Type: Small molecule

Representations

Synonyms (1): 5-(4-Phenoxyphenylsulfonamido)Pentylcarbamoylphosphonic Acid
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C(NCCCCCNS(=O)(=O)c1ccc(Oc2ccccc2)cc1)P(=O)(O)O

Standard InChI:  InChI=1S/C18H23N2O7PS/c21-18(28(22,23)24)19-13-5-2-6-14-20-29(25,26)17-11-9-16(10-12-17)27-15-7-3-1-4-8-15/h1,3-4,7-12,20H,2,5-6,13-14H2,(H,19,21)(H2,22,23,24)

Standard InChI Key:  RSXKZRJAIWEVPD-UHFFFAOYSA-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: 442.43

Molecular Weight (Monoisotopic): 442.0964

AlogP: 2.81

#Rotatable Bonds: 11

Polar Surface Area: 142.03

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.06

CX Basic pKa:

CX LogP: 1.74

CX LogD: -1.82

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.31

Np Likeness Score: -0.74

References

1. Reich R, Hoffman A, Veerendhar A, Maresca A, Innocenti A, Supuran CT, Breuer E..  (2012)  Carbamoylphosphonates control tumor cell proliferation and dissemination by simultaneously inhibiting carbonic anhydrase IX and matrix metalloproteinase-2. Toward nontoxic chemotherapy targeting tumor microenvironment.,  55  (17): [PMID:22894736] [10.1021/jm300981b]

2. Baidya SK, Banerjee S, Adhikari N, Jha T..  (2022)  Selective Inhibitors of Medium-Size S1' Pocket Matrix Metalloproteinases: A Stepping Stone of Future Drug Discovery.,  65  (16.0): [PMID:35969157] [10.1021/acs.jmedchem.1c01855]

Source

Source(1):

• Scientific Literature