Sodium (3E/Z)-(2-(1-(4,8-dimethylnon-3,7-dien-1-yl)-1H-1,2,3-triazol-4-yl)ethane-1,1-diyl)bis-(phosphonate)

ID: ALA3775876

Chembl Id: CHEMBL3775876

PubChem CID: 77108489

Max Phase: Preclinical

Molecular Formula: C15H23N3Na4O6P2

Molecular Weight: 407.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCC/C(C)=C/CCn1cc(CC(P(=O)([O-])[O-])P(=O)([O-])[O-])nn1.[Na+].[Na+].[Na+].[Na+]

Standard InChI:  InChI=1S/C15H27N3O6P2.4Na/c1-12(2)6-4-7-13(3)8-5-9-18-11-14(16-17-18)10-15(25(19,20)21)26(22,23)24;;;;/h6,8,11,15H,4-5,7,9-10H2,1-3H3,(H2,19,20,21)(H2,22,23,24);;;;/q;4*+1/p-4/b13-8+;;;;

Standard InChI Key:  DTOZLXJMIAVMAQ-MEVDHSCASA-J

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: 407.34

Molecular Weight (Monoisotopic): 407.1375

AlogP: 2.58

#Rotatable Bonds: 10

Polar Surface Area: 145.77

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.25

CX Basic pKa: 0.26

CX LogP: 0.63

CX LogD: -3.81

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.34

Np Likeness Score: 0.36

References

1. Wills VS, Allen C, Holstein SA, Wiemer DF..  (2015)  Potent Triazole Bisphosphonate Inhibitor of Geranylgeranyl Diphosphate Synthase.,  6  (12): [PMID:26713103] [10.1021/acsmedchemlett.5b00334]

2. Wills VS, Metzger JI, Allen C, Varney ML, Wiemer DF, Holstein SA..  (2017)  Bishomoisoprenoid triazole bisphosphonates as inhibitors of geranylgeranyl diphosphate synthase.,  25  (8): [PMID:28302510] [10.1016/j.bmc.2017.02.066]

3. Matthiesen RA, Varney ML, Xu PC, Rier AS, Wiemer DF, Holstein SA..  (2018)  α-Methylation enhances the potency of isoprenoid triazole bisphosphonates as geranylgeranyl diphosphate synthase inhibitors.,  26  (2): [PMID:29248353] [10.1016/j.bmc.2017.10.023]

4. Matthiesen RA, Varney ML, Xu PC, Rier AS, Wiemer DF, Holstein SA..  (2018)  α-Methylation enhances the potency of isoprenoid triazole bisphosphonates as geranylgeranyl diphosphate synthase inhibitors.,  26  (2): [PMID:29248353] [10.1016/j.bmc.2017.10.023]

Source

Source(1):

• Scientific Literature