Hexyl (2S,3S,6R)-6-(4-amino-2-oxopyrimidin-1(2H)-yl)-3-((S)-3-amino-5-(1-methylguanidino)pentanamido)-3,6-dihydro-2H-pyran-2-carboxylate; Blasticidin S hexyl ester

ID: ALA5279347

Max Phase: Preclinical

Molecular Formula: C23H38N8O5

Molecular Weight: 506.61

Names and Identifiers

Canonical SMILES:  CCCCCCOC(=O)[C@H]1O[C@@H](n2ccc(N)nc2=O)C=C[C@@H]1NC(=O)C[C@@H](N)CCN(C)C(=N)N

Standard InChI:  InChI=1S/C23H38N8O5/c1-3-4-5-6-13-35-21(33)20-16(28-18(32)14-15(24)9-11-30(2)22(26)27)7-8-19(36-20)31-12-10-17(25)29-23(31)34/h7-8,10,12,15-16,19-20H,3-6,9,11,13-14,24H2,1-2H3,(H3,26,27)(H,28,32)(H2,25,29,34)/t15-,16-,19+,20-/m0/s1

Standard InChI Key:  GRXSWDYOUYLUOT-FEHORTKBSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA5279347

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 506.61

Molecular Weight (Monoisotopic): 506.2965

AlogP: -0.18

#Rotatable Bonds: 13

Polar Surface Area: 204.67

Molecular Species: BASE

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 13.18

CX Basic pKa: 12.17

CX LogP: -0.92

CX LogD: -4.03

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.08

Np Likeness Score: 0.76

References

1. Gannett C, Banks P, Chuong C, Weger-Lucarelli J, Mevers E, Lowell AN..  (2023)  Semisynthetic blasticidin S ester derivatives show enhanced antibiotic activity.,  14  (4): [PMID:37122539] [10.1039/d2md00412g]

Source

Source(1):

• Scientific Literature