1-hydroxy-4-((Z)-7-((1R,2R,3R)-3-hydroxy-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enamido)butane-1,1-diyldiphosphonic acid

ID: ALA4102742

PubChem CID: 9808443

Max Phase: Preclinical

Molecular Formula: C24H43NO11P2

Molecular Weight: 583.55

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H43NO11P2/c1-2-3-6-10-18(26)13-14-20-19(21(27)17-22(20)28)11-7-4-5-8-12-23(29)25-16-9-15-24(30,37(31,32)33)38(34,35)36/h4,7,13-14,18-20,22,26,28,30H,2-3,5-6,8-12,15-17H2,1H3,(H,25,29)(H2,31,32,33)(H2,34,35,36)/b7-4-,14-13+/t18-,19+,20+,22+/m0/s1

Standard InChI Key:  VLSZLSIEZWDASB-DMKBRLEBSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4102742

   [1-hydroxy-4-[[(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoyl]amino]-1-phosphonobutyl]phosphonic 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: 583.55

Molecular Weight (Monoisotopic): 583.2311

AlogP: 2.06

#Rotatable Bonds: 18

Polar Surface Area: 221.92

Molecular Species: ACID

HBA: 7

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.69

CX Basic pKa: ┄

CX LogP: 0.43

CX LogD: -4.50

Aromatic Rings: ┄

Heavy Atoms: 38

QED Weighted: 0.07

Np Likeness Score: 1.19

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