4-{[3,3-Dimethyl-2-(3-methyl-2-methylamino-3-phenyl-butyrylamino)-butyryl]-methyl-amino}-2,5-dimethyl-hex-2-enoic acid

ID: ALA2096805

PubChem CID: 11454292

Max Phase: Preclinical

Molecular Formula: C27H43N3O4

Molecular Weight: 473.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN[C@H](C(=O)N[C@@H](C(=O)N(C)[C@H](/C=C(\C)C(=O)O)C(C)C)C(C)(C)C)C(C)(C)c1ccccc1

Standard InChI:  InChI=1S/C27H43N3O4/c1-17(2)20(16-18(3)25(33)34)30(10)24(32)22(26(4,5)6)29-23(31)21(28-9)27(7,8)19-14-12-11-13-15-19/h11-17,20-22,28H,1-10H3,(H,29,31)(H,33,34)/b18-16+/t20-,21-,22+/m1/s1

Standard InChI Key:  CNTMOLDWXSVYKD-TYOFZRJGSA-N

Molfile:  

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    3.0917   -1.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 34 32  2  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2096805

   (E,4S)-4-[[(2R)-3,3-dimethyl-2-[[(2S)-3-methyl-2-(methylamino)-3-phenylbutanoyl]amino]butanoyl]-methylamino]-2,5-dimethylhex-2-enoic 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: 473.66

Molecular Weight (Monoisotopic): 473.3254

AlogP: 3.60

#Rotatable Bonds: 10

Polar Surface Area: 98.74

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.21

CX Basic pKa: 8.41

CX LogP: 2.01

CX LogD: 1.98

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.45

Np Likeness Score: 1.50

References

1. Zask A, Birnberg G, Cheung K, Kaplan J, Niu C, Norton E, Suayan R, Yamashita A, Cole D, Tang Z, Krishnamurthy G, Williamson R, Khafizova G, Musto S, Hernandez R, Annable T, Yang X, Discafani C, Beyer C, Greenberger LM, Loganzo F, Ayral-Kaloustian S..  (2004)  Synthesis and biological activity of analogues of the antimicrotubule agent N,beta,beta-trimethyl-L-phenylalanyl-N(1)-[(1S,2E)-3-carboxy-1-isopropylbut-2-enyl]- N(1),3-dimethyl-L-valinamide (HTI-286).,  47  (19): [PMID:15341492] [10.1021/jm040056u]

Source

Source(1):

• Scientific Literature