(Z)-7-((1R,2R,3R)-2-((S,E)-3-(2-(4,4-diphosphonobutylthio)acetoxy)oct-1-enyl)-3-hydroxy-5-oxocyclopentyl)hept-5-enoic acid

ID: ALA4094989

PubChem CID: 9939839

Max Phase: Preclinical

Molecular Formula: C26H44O12P2S

Molecular Weight: 642.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC[C@@H](/C=C/[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCC(=O)O)OC(=O)CSCCCC(P(=O)(O)O)P(=O)(O)O

Standard InChI:  InChI=1S/C26H44O12P2S/c1-2-3-6-10-19(38-25(31)18-41-16-9-13-26(39(32,33)34)40(35,36)37)14-15-21-20(22(27)17-23(21)28)11-7-4-5-8-12-24(29)30/h4,7,14-15,19-21,23,26,28H,2-3,5-6,8-13,16-18H2,1H3,(H,29,30)(H2,32,33,34)(H2,35,36,37)/b7-4-,15-14+/t19-,20+,21+,23+/m0/s1

Standard InChI Key:  XERJJNDHXYZGQY-JSFDOGTHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4094989

   (Z)-7-[(1R,2R,3R)-2-[(E,3S)-3-[2-(4,4-diphosphonobutylsulfanyl)acetyl]oxyoct-1-enyl]-3-hydroxy-5-oxocyclopentyl]hept-5-enoic 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: 642.64

Molecular Weight (Monoisotopic): 642.2029

AlogP: 4.00

#Rotatable Bonds: 21

Polar Surface Area: 215.96

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.21

CX Basic pKa: ┄

CX LogP: 1.98

CX LogD: -5.74

Aromatic Rings: ┄

Heavy Atoms: 41

QED Weighted: 0.05

Np Likeness Score: 1.13

References

1. Xie H, Chen G, Young RN..  (2017)  Design, Synthesis, and Pharmacokinetics of a Bone-Targeting Dual-Action Prodrug for the Treatment of Osteoporosis.,  60  (16): [PMID:28699744] [10.1021/acs.jmedchem.6b00951]

Source

Source(1):

• Scientific Literature