Tripotassium salt of 4-(3-Phenoxy-phenyl)-1-phosphono-butane-1-sulfonic acid

ID: ALA351151

Cas Number: 157124-84-0

PubChem CID: 16730264

Max Phase: Preclinical

Molecular Formula: C16H16K3O7PS

Molecular Weight: 386.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BMS-187745 | BPH-652|157124-84-0|BPH-652 potassium|Potassium 4-(3-phenoxyphenyl)-1-phosphonatobutane-1-sulfonate|157124-84-0 (potassium)|CHEMBL351151|AYH5JV63N4|BPH 652|FT-0663419|Potassium4-(3-phenoxyphenyl)-1-phosphonatobutane-1-sulfonate|tripotassium;4-(3-phenoxyphenyl)-1-phosphonatobutane-1-sulfonate|Benzenebutanesulfonic acid, 3-phenoxy-alpha-phosphono-, tripotassium salt|TRIPOTASSIUM 4-(3-PHENOXYPHENYL)-1-PHOSPHONATOBUTANE-1-SULFONATE|4-(3-PHENOXYPHENYL)-1-PHOSPHONO-BUTANE-1-SULFONIC ACID;Show More⌵

Canonical SMILES:  O=P([O-])([O-])C(CCCc1cccc(Oc2ccccc2)c1)S(=O)(=O)[O-].[K+].[K+].[K+]

Standard InChI:  InChI=1S/C16H19O7PS.3K/c17-24(18,19)16(25(20,21)22)11-5-7-13-6-4-10-15(12-13)23-14-8-2-1-3-9-14;;;/h1-4,6,8-10,12,16H,5,7,11H2,(H2,17,18,19)(H,20,21,22);;;/q;3*+1/p-3

Standard InChI Key:  DRADVLDMPYYQDB-UHFFFAOYSA-K

Molfile:  

     RDKit          2D

 28 26  0  0  0  0  0  0  0  0999 V2000
    2.6167    2.8125    0.0000 K   0  0  0  0  0 15  0  0  0  0  0  0
   -5.1098    0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1109   -0.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3961   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6797   -0.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6825    0.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3979    1.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9696    1.1564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2536    0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538   -0.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5387   -0.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8248   -0.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8305    0.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5463    1.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1191    1.1764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5984    0.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3098    1.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273    0.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7387    1.1972    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.0333   -0.0454    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8583   -0.0466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2083   -0.0481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0393   -0.8704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500    1.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1571    0.4862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3197    1.9079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -1.0917    0.0000 K   0  0  0  0  0 15  0  0  0  0  0  0
    4.4000    1.8125    0.0000 K   0  0  0  0  0 15  0  0  0  0  0  0
  5  6  1  0
 13 14  2  0
 14  9  1  0
 13 15  1  0
  6  7  2  0
 15 16  1  0
  7  2  1  0
 16 17  1  0
  2  3  2  0
 17 18  1  0
  6  8  1  0
 18 19  1  0
 18 20  1  0
  8  9  1  0
 20 21  2  0
  3  4  1  0
 20 22  2  0
  9 10  2  0
 20 23  1  0
 19 24  1  0
 10 11  1  0
 19 25  2  0
  4  5  2  0
 19 26  1  0
 11 12  2  0
 12 13  1  0
M  CHG  6   1   1  23  -1  24  -1  26  -1  27   1  28   1
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: 386.36

Molecular Weight (Monoisotopic): 386.0589

AlogP: 3.19

#Rotatable Bonds: 8

Polar Surface Area: 121.13

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -1.11

CX Basic pKa: ┄

CX LogP: 2.27

CX LogD: -2.42

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.47

Np Likeness Score: -0.01

References

1. Magnin DR, Biller SA, Chen Y, Dickson JK, Fryszman OM, Lawrence RM, Logan JV, Sieber-McMaster ES, Sulsky RB, Traeger SC, Hsieh DC, Lan SJ, Rinehart JK, Harrity TW, Jolibois KG, Kunselman LK, Rich LC, Slusarchyk DA, Ciosek CP..  (1996)  alpha-Phosphonosulfonic acids: potent and selective inhibitors of squalene synthase.,  39  (3): [PMID:8576905] [10.1021/jm9507340]

2. Dickson JK, Biller SA, Magnin DR, Petrillo EW, Hillyer JW, Hsieh DC, Lan SJ, Rinehart JK, Gregg RE, Harrity TW, Jolibois KG, Kalinowski SS, Kunselman LK, Mookhtiar KA, Ciosek CP..  (1996)  Orally active squalene synthase inhibitors: bis((acyloxy)alkyl) prodrugs of the alpha-phosphonosulfonic acid moiety.,  39  (3): [PMID:8576906] [10.1021/jm950735s]

3. Song Y, Lin FY, Yin F, Hensler M, Rodrígues Poveda CA, Mukkamala D, Cao R, Wang H, Morita CT, González Pacanowska D, Nizet V, Oldfield E..  (2009)  Phosphonosulfonates are potent, selective inhibitors of dehydrosqualene synthase and staphyloxanthin biosynthesis in Staphylococcus aureus.,  52  (4): [PMID:19191557] [10.1021/jm801023u]

4. Wang Y, Di H, Chen F, Xu Y, Xiao Q, Wang X, Wei H, Lu Y, Zhang L, Zhu J, Lan L, Li J..  (2016)  Discovery of Benzocycloalkane Derivatives Efficiently Blocking Bacterial Virulence for the Treatment of Methicillin-Resistant S. aureus (MRSA) Infections by Targeting Diapophytoene Desaturase (CrtN).,  59  (10): [PMID:27139780] [10.1021/acs.jmedchem.6b00122]

5. Dharmaraja AT..  (2017)  Role of Reactive Oxygen Species (ROS) in Therapeutics and Drug Resistance in Cancer and Bacteria.,  60  (8): [PMID:28135088] [10.1021/acs.jmedchem.6b01243]

6. Li B, Ni S, Mao F, Chen F, Liu Y, Wei H, Chen W, Zhu J, Lan L, Li J..  (2018)  Novel Terminal Bipheny-Based Diapophytoene Desaturases (CrtN) Inhibitors as Anti-MRSA/VISR/LRSA Agents with Reduced hERG Activity.,  61  (1): [PMID:29243920] [10.1021/acs.jmedchem.7b01300]

Source

Source(1):

• Scientific Literature