Sodium(E)-(2-(1-(3,7-dimethylocta-2,6-dien-1-yl)-1H-1,2,3-triazol-4-yl)ethane-1,1-diyl)bis(phosphonate)

ID: ALA3262351

Chembl Id: CHEMBL3262351

PubChem CID: 71521669

Max Phase: Preclinical

Molecular Formula: C14H21N3Na4O6P2

Molecular Weight: 393.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCC/C(C)=C/Cn1cc(CC(P(=O)([O-])[O-])P(=O)([O-])[O-])nn1.[Na+].[Na+].[Na+].[Na+]

Standard InChI:  InChI=1S/C14H25N3O6P2.4Na/c1-11(2)5-4-6-12(3)7-8-17-10-13(15-16-17)9-14(24(18,19)20)25(21,22)23;;;;/h5,7,10,14H,4,6,8-9H2,1-3H3,(H2,18,19,20)(H2,21,22,23);;;;/q;4*+1/p-4/b12-7+;;;;

Standard InChI Key:  APPIOIDSLGCBAD-BLSNBFPRSA-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: 393.32

Molecular Weight (Monoisotopic): 393.1219

AlogP: 2.19

#Rotatable Bonds: 9

Polar Surface Area: 145.77

Molecular Species: ACID

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.26

CX Basic pKa: 0.32

CX LogP: 0.34

CX LogD: -4.09

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.37

Np Likeness Score: 0.41

References

1. Zhou X, Ferree SD, Wills VS, Born EJ, Tong H, Wiemer DF, Holstein SA..  (2014)  Geranyl and neryl triazole bisphosphonates as inhibitors of geranylgeranyl diphosphate synthase.,  22  (9): [PMID:24726306] [10.1016/j.bmc.2014.03.014]

2. 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]

3. Fairweather AER, Goetz DB, Schroeder CM, Bhuiyan NH, Varney ML, Wiemer DF, Holstein SA..  (2021)  Impact of α-modifications on the activity of triazole bisphosphonates as geranylgeranyl diphosphate synthase inhibitors.,  44  [PMID:34298413] [10.1016/j.bmc.2021.116307]

Source

Source(1):

• Scientific Literature