(S)-3-((3S,6S)-3-((2S,3S)-2-acetamido-3-methylpentanamido)-4-oxo-1,2,3,4,6,7-hexahydroazepino[3,2,1-hi]indole-6-carboxamido)-4-oxobutanoic acid

ID: ALA428244

PubChem CID: 44453610

Max Phase: Preclinical

Molecular Formula: C25H32N4O7

Molecular Weight: 500.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NC(C)=O)C(=O)N[C@H]1CCc2cccc3c2N(C1=O)[C@H](C(=O)N[C@H](C=O)CC(=O)O)C3

Standard InChI:  InChI=1S/C25H32N4O7/c1-4-13(2)21(26-14(3)31)24(35)28-18-9-8-15-6-5-7-16-10-19(29(22(15)16)25(18)36)23(34)27-17(12-30)11-20(32)33/h5-7,12-13,17-19,21H,4,8-11H2,1-3H3,(H,26,31)(H,27,34)(H,28,35)(H,32,33)/t13-,17-,18-,19-,21-/m0/s1

Standard InChI Key:  PHKDXBRYQQCBAI-RUHZZDLRSA-N

Molfile:  

     RDKit          2D

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    8.0978  -31.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  7  3  1  0
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  4  5  1  0
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  7 15  2  0
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 12 16  1  1
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 34 36  2  0
 16 17  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA428244

   (3S)-3-[[(2S,11S)-11-[[(2S,3S)-2-acetamido-3-methylpentanoyl]amino]-12-oxo-1-azatricyclo[6.4.1.04,13]trideca-4,6,8(13)-triene-2-carbonyl]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: 500.55

Molecular Weight (Monoisotopic): 500.2271

AlogP: 0.08

#Rotatable Bonds: 10

Polar Surface Area: 161.98

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.70

CX Basic pKa: ┄

CX LogP: -0.15

CX LogD: -3.45

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.33

Np Likeness Score: 0.28

References

1. Maryanoff BE, Costanzo MJ..  (2008)  Inhibitors of proteases and amide hydrolases that employ an alpha-ketoheterocycle as a key enabling functionality.,  16  (4): [PMID:18053726] [10.1016/j.bmc.2007.11.015]

Source

Source(1):

• Scientific Literature