(S)-4-((S)-1-carboxy-2-phenylethylamino)-3-(2-((3S,3aR,5S,7S,7aS)-3-hydroxy-5-isobutoxy-7-((3-phenylpropanoyloxy)methyl)-hexahydropyrano[3,4-b]pyrrol-1(2H)-yl)acetamido)-4-oxobutanoic acid

ID: ALA372558

Chembl Id: CHEMBL372558

PubChem CID: 44405200

Max Phase: Preclinical

Molecular Formula: C36H47N3O11

Molecular Weight: 697.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CO[C@@H]1C[C@@H]2[C@@H]([C@@H](COC(=O)CCc3ccccc3)O1)N(CC(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](Cc1ccccc1)C(=O)O)C[C@H]2O

Standard InChI:  InChI=1S/C36H47N3O11/c1-22(2)20-49-33-16-25-28(40)18-39(34(25)29(50-33)21-48-32(44)14-13-23-9-5-3-6-10-23)19-30(41)37-26(17-31(42)43)35(45)38-27(36(46)47)15-24-11-7-4-8-12-24/h3-12,22,25-29,33-34,40H,13-21H2,1-2H3,(H,37,41)(H,38,45)(H,42,43)(H,46,47)/t25-,26-,27-,28+,29+,33-,34-/m0/s1

Standard InChI Key:  SWJHYKDPDVGNSJ-OHMVQTBZSA-N

Alternative Forms

1. Parent:

   

   ALA372558

   (3S)-3-[[2-[(3S,3aR,5S,7S,7aS)-3-hydroxy-5-(2-methylpropoxy)-7-(3-phenylpropanoyloxymethyl)-3,3a,4,5,7,7a-hexahydro-2H-pyrano[3,4-b]pyrrol-1-yl]acetyl]amino]-4-[[(1S)-1-carboxy-2-phenylethyl]amino]-4-oxobutanoic acid

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: 697.78

Molecular Weight (Monoisotopic): 697.3211

AlogP: 1.38

#Rotatable Bonds: 18

Polar Surface Area: 201.03

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 14

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.40

CX Basic pKa: 6.64

CX LogP: -0.71

CX LogD: -4.25

Aromatic Rings: 2

Heavy Atoms: 50

QED Weighted: 0.14

Np Likeness Score: 0.51

References

1. Fuertes MJ, Kaur J, Deb P, Cooperman BS, Smith AB..  (2005)  Design, synthesis, and evaluation of octahydropyranopyrrole-based inhibitors of mammalian ribonucleotide reductase.,  15  (23): [PMID:16176875] [10.1016/j.bmcl.2005.08.062]

Source

Source(1):

• Scientific Literature