{1-Hydroxy-2-[3'-(naphthalene-2-sulfonylamino)-biphenyl-3-yl]-1-phosphono-ethyl}-phosphonic acid

ID: ALA259026

Cas Number: 946417-21-6

PubChem CID: 16122555

Product Number: B608192, Order Now?

Max Phase: Preclinical

Molecular Formula: C24H23NO9P2S

Molecular Weight: 563.46

Molecule Type: Small molecule

Names and Identifiers

Synonyms: BPH-675 | BPH-675|[1-hydroxy-2-[3-[3-(naphthalen-2-ylsulfonylamino)phenyl]phenyl]-1-phosphonoethyl]phosphonic acid|946417-21-6|1-Hydroxy-2-[3'-(Naphthalene-2-Sulfonylamino)-Biphenyl-3-Yl]ethylidene-1,1-Bisphosphonic Acid|BPH675|BPH 675|bisphosphonate, 6|CHEMBL259026|GTPL7975|SCHEMBL2388987|BDBM25284|AKOS040750898|Q27075451|(1-HYDROXY-2-{3'-[(2-NAPHTHYLSULFONYL)AMINO]BIPHENYL-3-YL}ETHANE-1,1-DIYL)BIS(PHOSPHONIC ACID)|(1-hydroxy-2-{3'-[(naphthalen-2-ylsulfonyl)amino]biphenyl-3-yl}ethane-1,1-diyl)bShow More⌵

Canonical SMILES:  O=P(O)(O)C(O)(Cc1cccc(-c2cccc(NS(=O)(=O)c3ccc4ccccc4c3)c2)c1)P(=O)(O)O

Standard InChI:  InChI=1S/C24H23NO9P2S/c26-24(35(27,28)29,36(30,31)32)16-17-5-3-8-19(13-17)20-9-4-10-22(14-20)25-37(33,34)23-12-11-18-6-1-2-7-21(18)15-23/h1-15,25-26H,16H2,(H2,27,28,29)(H2,30,31,32)

Standard InChI Key:  MZVWVRVNMXTDAK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.2709   -2.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2709   -2.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5565   -3.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1275   -3.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4131   -2.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6986   -1.6345    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2697   -1.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4118    0.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7316   -1.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1441   -1.9364    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8586   -1.5239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5566   -2.6509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4297   -2.3489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3191   -0.5075    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9066    0.2070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6047   -0.9200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0336   -0.0950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4461   -0.8095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1 10  1  0
  7  2  1  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
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  8  7  2  0
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  9 10  2  0
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 21 20  1  0
 23 21  1  0
 22 21  2  0
 22 26  1  0
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 24 25  1  0
 25 26  2  0
 27 26  1  0
 27 28  1  0
 28 37  1  0
 28 33  1  0
 28 29  1  0
 30 29  2  0
 32 29  1  0
 31 29  1  0
 34 33  2  0
 35 33  1  0
 36 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA259026

   BPH-675

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: 563.46

Molecular Weight (Monoisotopic): 563.0569

AlogP: 3.85

#Rotatable Bonds: 8

Polar Surface Area: 181.46

Molecular Species: ACID

HBA: 5

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.69

CX Basic pKa: ┄

CX LogP: 2.66

CX LogD: -2.42

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.17

Np Likeness Score: -0.71

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]

Source

Source(1):

• Scientific Literature