(S)-3-((S)-7-hydroxy-3-(2-methylbut-3-en-2-yl)-2-oxoindolin-3-yl)-2-((S)-2-hydroxy-3-phenylpropanamido)propanoic acid

ID: ALA4209418

PubChem CID: 139589765

Max Phase: Preclinical

Molecular Formula: C25H28N2O6

Molecular Weight: 452.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(C)(C)[C@]1(C[C@H](NC(=O)[C@@H](O)Cc2ccccc2)C(=O)O)C(=O)Nc2c(O)cccc21

Standard InChI:  InChI=1S/C25H28N2O6/c1-4-24(2,3)25(16-11-8-12-18(28)20(16)27-23(25)33)14-17(22(31)32)26-21(30)19(29)13-15-9-6-5-7-10-15/h4-12,17,19,28-29H,1,13-14H2,2-3H3,(H,26,30)(H,27,33)(H,31,32)/t17-,19-,25-/m0/s1

Standard InChI Key:  TXVLBRMNUYNGCT-KMEZTADASA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    3.9749   -8.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5666   -8.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3913   -8.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5707   -9.5830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2831   -9.1670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3569   -9.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3557  -10.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0705  -11.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0687   -9.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7846   -9.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889  -10.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5815  -10.9301    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0671  -10.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081   -9.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5241   -9.8752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5170   -8.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3420   -8.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1008   -7.7339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3491   -9.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7652  -10.5834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7580   -9.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3564  -11.2998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5902  -10.5791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7724  -12.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3591  -12.7274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7745  -13.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6003  -13.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0090  -12.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5912  -12.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -8.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8459   -7.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8921  -10.2488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0695  -11.9148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  2  1  6
  5  4  1  0
  6  7  2  0
  7  8  1  0
  8 11  2  0
 10  9  2  0
  9  6  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13  4  1  0
  4 10  1  0
  5 14  1  0
 14 15  1  0
 14 16  1  1
 16 17  1  0
 16 18  2  0
 15 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 20 23  1  1
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
  2 30  1  0
 30 31  2  0
 13 32  2  0
  8 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4209418

   ---

Molecule Features

Natural Product: Yes

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: 452.51

Molecular Weight (Monoisotopic): 452.1947

AlogP: 2.36

#Rotatable Bonds: 9

Polar Surface Area: 135.96

Molecular Species: ACID

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.74

CX Basic pKa: ┄

CX LogP: 2.86

CX LogD: -0.45

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.29

Np Likeness Score: 1.36

References

1. Aparicio-Cuevas MA, Rivero-Cruz I, Sánchez-Castellanos M, Menéndez D, Raja HA, Joseph-Nathan P, González MDC, Figueroa M..  (2017)  Dioxomorpholines and Derivatives from a Marine-Facultative Aspergillus Species.,  80  (8): [PMID:28796494] [10.1021/acs.jnatprod.7b00331]

Source

Source(1):

• Scientific Literature