(4S,7S,12bR)-7-[[(1S)-1-carboxy-3-phenyl-propyl]amino]-6-oxo-2,3,4,7,8,12b-hexahydro-1H-pyrido[2,1-a][2]benzazepine-4-carboxylic acid

ID: ALA5272537

Max Phase: Preclinical

Molecular Formula: C25H28N2O5

Molecular Weight: 436.51

Names and Identifiers

Canonical SMILES:  O=C(O)[C@H](CCc1ccccc1)N[C@H]1Cc2ccccc2[C@H]2CCC[C@@H](C(=O)O)N2C1=O

Standard InChI:  InChI=1S/C25H28N2O5/c28-23-20(26-19(24(29)30)14-13-16-7-2-1-3-8-16)15-17-9-4-5-10-18(17)21-11-6-12-22(25(31)32)27(21)23/h1-5,7-10,19-22,26H,6,11-15H2,(H,29,30)(H,31,32)/t19-,20-,21+,22-/m0/s1

Standard InChI Key:  MFPBDCIKVMSRDU-KJJMTIBFSA-N

Molfile:  

 
     RDKit          2D

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   -2.2445   -1.2449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5815   -0.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7942    0.6818    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.9498   -1.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -2.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9436   -2.4921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6124   -1.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 28 29  2  0
 28 30  1  0
 31 27  1  0
 31 22  1  0
 32 31  1  0
 32 14  1  0
 32 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5272537

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 436.51

Molecular Weight (Monoisotopic): 436.1998

AlogP: 2.79

#Rotatable Bonds: 7

Polar Surface Area: 106.94

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.16

CX Basic pKa: 7.89

CX LogP: 0.86

CX LogD: -2.09

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.62

Np Likeness Score: 0.14

References

1. Van der Poorten O, Knuhtsen A, Sejer Pedersen D, Ballet S, Tourwé D..  (2016)  Side Chain Cyclized Aromatic Amino Acids: Great Tools as Local Constraints in Peptide and Peptidomimetic Design.,  59  (24): [PMID:27690430] [10.1021/acs.jmedchem.6b01029]

Source

Source(1):

• Scientific Literature