(S)-4-((4-(2-(2-(benzyloxycarbonylamino)acetamido)-5-guanidinopentanamido)benzyloxy)carbonylamino)-1-hydroxybutane-1,1-diyldiphosphonic acid

ID: ALA4067569

PubChem CID: 137633808

Max Phase: Preclinical

Molecular Formula: C28H41N7O13P2

Molecular Weight: 745.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@H](NC(=O)CNC(=O)OCc1ccccc1)C(=O)Nc1ccc(COC(=O)NCCCC(O)(P(=O)(O)O)P(=O)(O)O)cc1

Standard InChI:  InChI=1S/C28H41N7O13P2/c29-25(30)31-14-4-8-22(35-23(36)16-33-27(39)48-17-19-6-2-1-3-7-19)24(37)34-21-11-9-20(10-12-21)18-47-26(38)32-15-5-13-28(40,49(41,42)43)50(44,45)46/h1-3,6-7,9-12,22,40H,4-5,8,13-18H2,(H,32,38)(H,33,39)(H,34,37)(H,35,36)(H4,29,30,31)(H2,41,42,43)(H2,44,45,46)/t22-/m0/s1

Standard InChI Key:  XIFOLFJVUICJGI-QFIPXVFZSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4067569

   ---

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: 745.62

Molecular Weight (Monoisotopic): 745.2238

AlogP: 0.31

#Rotatable Bonds: 19

Polar Surface Area: 332.05

Molecular Species: ZWITTERION

HBA: 10

HBD: 12

#RO5 Violations: 2

HBA (Lipinski): 20

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.69

CX Basic pKa: 11.80

CX LogP: -1.67

CX LogD: -4.03

Aromatic Rings: 2

Heavy Atoms: 50

QED Weighted: 0.04

Np Likeness Score: -0.30

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