(S)-2-amino-5-((R)-3-(6-carbamoyl-7-methoxyquinolin-4-ylthio)-1-(carboxymethylamino)-1-oxopropan-2-ylamino)-5-oxopentanoic acid

ID: ALA3527508

PubChem CID: 118753336

Max Phase: Preclinical

Molecular Formula: C21H25N5O8S

Molecular Weight: 507.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2nccc(SC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O)c2cc1C(N)=O

Standard InChI:  InChI=1S/C21H25N5O8S/c1-34-15-7-13-10(6-11(15)19(23)30)16(4-5-24-13)35-9-14(20(31)25-8-18(28)29)26-17(27)3-2-12(22)21(32)33/h4-7,12,14H,2-3,8-9,22H2,1H3,(H2,23,30)(H,25,31)(H,26,27)(H,28,29)(H,32,33)/t12-,14-/m0/s1

Standard InChI Key:  ISCLPTLEFCRHEZ-JSGCOSHPSA-N

Molfile:  

     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
   12.8164   -1.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8147   -2.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5311   -3.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5283   -1.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1004   -1.4142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3889   -1.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1026   -3.0666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3872   -2.6533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1016   -3.8916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2456   -1.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2467   -2.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9597   -3.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6764   -2.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6692   -1.8145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9553   -1.4100    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9623   -3.8838    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.6752   -4.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6778   -5.1232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3950   -5.5334    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9633   -5.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2504   -5.1235    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9659   -6.3588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5358   -5.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8228   -5.1280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8176   -4.3031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1057   -5.5428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1096   -5.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8225   -5.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1070   -4.2937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5371   -5.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2501   -5.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9647   -5.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2526   -6.3536    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6853   -5.5233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9655   -4.2880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 11  2  0
 10  4  2  0
  4  1  1  0
  1  5  1  0
  5  6  1  0
  2  7  1  0
  7  8  1  0
  7  9  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 12 16  1  0
 16 17  1  0
 18 17  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 20 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  2  0
 19 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
 31 30  1  0
 31 32  1  0
 31 33  1  1
 32 34  1  0
 32 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3527508

   ---

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: 507.53

Molecular Weight (Monoisotopic): 507.1424

AlogP: -0.69

#Rotatable Bonds: 13

Polar Surface Area: 224.03

Molecular Species: ZWITTERION

HBA: 9

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.73

CX Basic pKa: 9.31

CX LogP: -5.37

CX LogD: -7.53

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.19

Np Likeness Score: -0.13

References

1. Inoue K, Asai N, Mizuo H, Fukuda K, Kusano K, Yoshimura T..  (2012)  Unique metabolic pathway of [(14)C]lenvatinib after oral administration to male cynomolgus monkey.,  40  (4): [PMID:22207053] [10.1124/dmd.111.043281]

Source

Source(1):

• Scientific Literature