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

ID: ALA4072689

PubChem CID: 137639162

Max Phase: Preclinical

Molecular Formula: C32H49N7O13P2

Molecular Weight: 801.73

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C32H49N7O13P2/c1-21(2)18-26(39-31(43)52-19-22-8-4-3-5-9-22)28(41)38-25(10-6-16-35-29(33)34)27(40)37-24-13-11-23(12-14-24)20-51-30(42)36-17-7-15-32(44,53(45,46)47)54(48,49)50/h3-5,8-9,11-14,21,25-26,44H,6-7,10,15-20H2,1-2H3,(H,36,42)(H,37,40)(H,38,41)(H,39,43)(H4,33,34,35)(H2,45,46,47)(H2,48,49,50)/t25-,26-/m0/s1

Standard InChI Key:  LNHQNHDOXDIOND-UIOOFZCWSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4072689

   ---

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: 801.73

Molecular Weight (Monoisotopic): 801.2864

AlogP: 1.72

#Rotatable Bonds: 21

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: 11.79

CX LogP: 0.07

CX LogD: -2.29

Aromatic Rings: 2

Heavy Atoms: 54

QED Weighted: 0.04

Np Likeness Score: -0.14

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