[2-(3-dibenzofuran-4-yl-phenyl)-1-hydroxy-1-phosphono-ethyl]-phosphonic acid

ID: ALA411274

Cas Number: 946417-20-5

PubChem CID: 16122553

Product Number: B608191, Order Now?

Max Phase: Preclinical

Molecular Formula: C20H18O8P2

Molecular Weight: 448.30

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BPH-629 | BPH-629|[2-(3-dibenzofuran-4-yl-phenyl)-1-hydroxy-1-phosphono-ethyl]-phosphonic acid|[2-(3-dibenzofuran-4-ylphenyl)-1-hydroxy-1-phosphonoethyl]phosphonic acid|946417-20-5|B29|BPH629|BPH 629|bisphosphonate, 8|CHEMBL411274|GTPL7976|SCHEMBL23752182|BDBM25288|AKOS040750897|DB07410|NS00071381|Q27075449|[2-(3-dibenzo[b,d]furan-4-ylphenyl)-1-hydroxyethane-1,1-diyl]bis(phosphonic acid)|[1-hydroxy-2-(3-{8-oxatricyclo[7.4.0.0^{2,7}]trideca-1(13),2,4,6,9,11-hexaen-6-yl}phenyl)-1-phosphonoethyl]phShow More⌵

Canonical SMILES:  O=P(O)(O)C(O)(Cc1cccc(-c2cccc3c2oc2ccccc23)c1)P(=O)(O)O

Standard InChI:  InChI=1S/C20H18O8P2/c21-20(29(22,23)24,30(25,26)27)12-13-5-3-6-14(11-13)15-8-4-9-17-16-7-1-2-10-18(16)28-19(15)17/h1-11,21H,12H2,(H2,22,23,24)(H2,25,26,27)

Standard InChI Key:  BYVXAUZOTGITQZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    4.0538    4.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058    4.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4128    4.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6677    3.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1157    3.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3087    3.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6413    2.7580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9738    3.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2288    4.0276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6767    4.6407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8698    4.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6148    3.6845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1669    3.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9119    2.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1050    2.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4640    1.6737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090    0.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4020    0.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8500    1.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430    1.1591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2119    0.3745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5727    0.1196    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.3573   -0.1354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3178   -0.6650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8277    0.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9965    0.6295    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2515   -0.1552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7811    0.8844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7416    1.4141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4668   -0.4101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0
  2  1  1  0
  1  9  1  0
  3  2  2  0
  4  3  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  8  7  1  0
  9  8  2  0
 13  8  1  0
 10  9  1  0
 11 10  2  0
 11 12  1  0
 12 13  2  0
 14 13  1  0
 16 14  2  0
 15 14  1  0
 15 19  2  0
 17 16  1  0
 17 18  2  0
 18 19  1  0
 20 19  1  0
 20 21  1  0
 21 22  1  0
 21 26  1  0
 21 30  1  0
 23 22  2  0
 25 22  1  0
 24 22  1  0
 27 26  2  0
 28 26  1  0
 29 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA411274

   BPH-629

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: 448.30

Molecular Weight (Monoisotopic): 448.0477

AlogP: 3.80

#Rotatable Bonds: 5

Polar Surface Area: 148.43

Molecular Species: ACID

HBA: 4

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.69

CX Basic pKa: ┄

CX LogP: 2.47

CX LogD: -2.47

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.29

Np Likeness Score: 0.28

References

1. Guo RT, Cao R, Liang PH, Ko TP, Chang TH, Hudock MP, Jeng WY, Chen CK, Zhang Y, Song Y, Kuo CJ, Yin F, Oldfield E, Wang AH..  (2007)  Bisphosphonates target multiple sites in both cis- and trans-prenyltransferases.,  104  (24): [PMID:17535895] [10.1073/pnas.0702254104]

2. K-M Chen C, Hudock MP, Zhang Y, Guo RT, Cao R, No JH, Liang PH, Ko TP, Chang TH, Chang SC, Song Y, Axelson J, Kumar A, Wang AH, Oldfield E..  (2008)  Inhibition of geranylgeranyl diphosphate synthase by bisphosphonates: a crystallographic and computational investigation.,  51  (18): [PMID:18800762] [10.1021/jm800325y]

3. Zhang Y, Fu-Yang Lin, Li K, Zhu W, Liu YL, Cao R, Pang R, Lee E, Axelson J, Hensler M, Wang K, Molohon KJ, Wang Y, Mitchell DA, Nizet V, Oldfield E..  (2012)  HIV-1 Integrase Inhibitor-Inspired Antibacterials Targeting Isoprenoid Biosynthesis.,  3  (5): [PMID:22662288] [10.1021/ml300038t]

4. Malwal SR, Chen L, Hicks H, Qu F, Liu W, Shillo A, Law WX, Zhang J, Chandnani N, Han X, Zheng Y, Chen CC, Guo RT, AbdelKhalek A, Seleem MN, Oldfield E..  (2019)  Discovery of Lipophilic Bisphosphonates That Target Bacterial Cell Wall and Quinone Biosynthesis.,  62  (5): [PMID:30730737] [10.1021/acs.jmedchem.8b01878]

Source

Source(1):

• Scientific Literature