2-((S)-((2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxytetrahydrofuran-2-yloxy)((2S,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)-N-(4-butoxyphenyl)-1,4-dimethyl-3-oxo-2,3,4,7-tetrahydro-1H-1,4-diazepine-5-carboxamide

ID: ALA4469776

Chembl Id: CHEMBL4469776

PubChem CID: 71654614

Max Phase: Preclinical

Molecular Formula: C32H44N6O12

Molecular Weight: 704.73

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCOc1ccc(NC(=O)C2=CCN(C)[C@@H]([C@H](O[C@@H]3O[C@H](CN)[C@@H](O)[C@H]3O)[C@H]3O[C@@H](n4ccc(=O)[nH]c4=O)[C@H](O)[C@@H]3O)C(=O)N2C)cc1

Standard InChI:  InChI=1S/C32H44N6O12/c1-4-5-14-47-17-8-6-16(7-9-17)34-28(44)18-10-12-36(2)21(29(45)37(18)3)26(50-31-25(43)22(40)19(15-33)48-31)27-23(41)24(42)30(49-27)38-13-11-20(39)35-32(38)46/h6-11,13,19,21-27,30-31,40-43H,4-5,12,14-15,33H2,1-3H3,(H,34,44)(H,35,39,46)/t19-,21+,22-,23+,24-,25-,26+,27+,30-,31+/m1/s1

Standard InChI Key:  GIMVEPLDJNFFMQ-KDHSHZOVSA-N

Alternative Forms

1. Parent:

   

   ALA4469776

   (2S)-2-[(S)-[(2S,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxy-tetrahydrofuran-2-yl]oxy-[(2S,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl]-N-(4-butoxyphenyl)-1,4-dimethyl-3-oxo-2,7-dihydro-1,4-diazepine-5-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 704.73

Molecular Weight (Monoisotopic): 704.3017

AlogP: -2.58

#Rotatable Bonds: 12

Polar Surface Area: 251.37

Molecular Species: BASE

HBA: 15

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 18

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 9.70

CX Basic pKa: 8.75

CX LogP: -2.32

CX LogD: -3.49

Aromatic Rings: 2

Heavy Atoms: 50

QED Weighted: 0.11

Np Likeness Score: 0.48

References

1. Patel B, Ryan P, Makwana V, Zunk M, Rudrawar S, Grant G..  (2019)  Caprazamycins: Promising lead structures acting on a novel antibacterial target MraY.,  171  [PMID:30933853] [10.1016/j.ejmech.2019.01.071]

2. Arbour CA,Imperiali B.  (2020)  Uridine natural products: Challenging targets and inspiration for novel small molecule inhibitors.,  28  (18): [PMID:32828427] [10.1016/j.bmc.2020.115661]

Source

Source(1):

• Scientific Literature