(4S,7S,10R,11S,12S)-12-[(1R)-1-hydroxyethyl]-10-methyl-17,21-dioxa-8-thia-2,5,14-triazapentacyclo[21.3.1.1^{4,7}.0^{9,15}.0^{11,14}]octacosa-1(27),9(15),23,25-tetraene-3,13,16,22-tetrone

ID: ALA2431071

PubChem CID: 73347804

Max Phase: Preclinical

Molecular Formula: C25H29N3O7S

Molecular Weight: 515.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H](O)[C@H]1C(=O)N2C3=C(S[C@@H]4CN[C@@H](C4)C(=O)Nc4cccc(c4)C(=O)OCCCOC3=O)[C@H](C)[C@H]12

Standard InChI:  InChI=1S/C25H29N3O7S/c1-12-19-18(13(2)29)23(31)28(19)20-21(12)36-16-10-17(26-11-16)22(30)27-15-6-3-5-14(9-15)24(32)34-7-4-8-35-25(20)33/h3,5-6,9,12-13,16-19,26,29H,4,7-8,10-11H2,1-2H3,(H,27,30)/t12-,13-,16+,17+,18-,19-/m1/s1

Standard InChI Key:  HFFBFNZMWTYVKV-CELYIQNJSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2431071

   (4S,7S,10R,11S,12S)-12-[(1R)-1-hydroxyethyl]-10-methyl-17,21-dioxa-8-thia-2,5,14-triazapentacyclo[21.3.1.14,7.09,15.011,14]octacosa-1(26),9(15),23(27),24-tetraene-3,13,16,22-tetrone

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: 515.59

Molecular Weight (Monoisotopic): 515.1726

AlogP: 1.26

#Rotatable Bonds: 1

Polar Surface Area: 134.27

Molecular Species: BASE

HBA: 9

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.98

CX Basic pKa: 8.99

CX LogP: -0.02

CX LogD: -1.61

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.37

Np Likeness Score: 0.74

References

1. Singh SB, Rindgen D, Bradley P, Cama L, Sun W, Hafey MJ, Suzuki T, Wang N, Wu H, Zhang B, Wang L, Ji C, Yu H, Soll R, Olsen DB, Meinke PT, Nicoll-Griffith DA..  (2013)  Design, synthesis, and evaluation of prodrugs of ertapenem.,  4  (8): [PMID:24900737] [10.1021/ml400092n]

2. Singh SB, Rindgen D, Bradley P, Suzuki T, Wang N, Wu H, Zhang B, Wang L, Ji C, Yu H, Soll RM, Olsen DB, Meinke PT, Nicoll-Griffith DA..  (2014)  Design, synthesis, structure-function relationship, bioconversion, and pharmacokinetic evaluation of ertapenem prodrugs.,  57  (20): [PMID:25265501] [10.1021/jm500879a]

Source

Source(1):

• Scientific Literature