(S)-2-((S)-2-((S)-2-((R)-2-amino-3-mercaptopropylamino)-3-methylbutoxy)-3-phenylpropanamido)-4-(methylsulfonyl)butanoic acid

ID: ALA3218393

PubChem CID: 90665660

Max Phase: Preclinical

Molecular Formula: C22H37N3O6S2

Molecular Weight: 503.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)[C@@H](CO[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCS(C)(=O)=O)C(=O)O)NC[C@@H](N)CS

Standard InChI:  InChI=1S/C22H37N3O6S2/c1-15(2)19(24-12-17(23)14-32)13-31-20(11-16-7-5-4-6-8-16)21(26)25-18(22(27)28)9-10-33(3,29)30/h4-8,15,17-20,24,32H,9-14,23H2,1-3H3,(H,25,26)(H,27,28)/t17-,18+,19-,20+/m1/s1

Standard InChI Key:  DBWZOKRHHKZPJP-WCIQWLHISA-N

Molfile:  

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    9.7974   -7.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0829   -9.1789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5140   -8.3539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3755  -11.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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 30 32  2  0
 30 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3218393

   (2S)-2-[[(2S)-2-[(2S)-2-[[(2R)-2-amino-3-sulfanylpropyl]amino]-3-methylbutoxy]-3-phenylpropanoyl]amino]-4-methylsulfonylbutanoic 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: 503.69

Molecular Weight (Monoisotopic): 503.2124

AlogP: 0.49

#Rotatable Bonds: 16

Polar Surface Area: 147.82

Molecular Species: ZWITTERION

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.10

CX Basic pKa: 9.42

CX LogP: -2.15

CX LogD: -2.25

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.20

Np Likeness Score: -0.05

References

1. Ochocki JD, Distefano MD..  (2013)  Prenyltransferase Inhibitors: Treating Human Ailments from Cancer to Parasitic Infections.,  4  (3): [PMID:25530833] [10.1039/c2md20299a]

Source

Source(1):

• Scientific Literature