2-((2S,5S,8R,11S)-5-((7-bromo-1H-indol-3-yl)methyl)-11-(3-guanidinopropyl)-8-isopropyl-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentaazacyclopentadecan-2-yl)acetic acid

ID: ALA4791029

PubChem CID: 162671754

Max Phase: Preclinical

Molecular Formula: C28H38BrN9O7

Molecular Weight: 692.57

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)[C@H]1NC(=O)[C@H](Cc2c[nH]c3c(Br)cccc23)NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CCCNC(=N)N)NC1=O

Standard InChI:  InChI=1S/C28H38BrN9O7/c1-13(2)22-27(45)36-17(7-4-8-32-28(30)31)24(42)34-12-20(39)35-19(10-21(40)41)25(43)37-18(26(44)38-22)9-14-11-33-23-15(14)5-3-6-16(23)29/h3,5-6,11,13,17-19,22,33H,4,7-10,12H2,1-2H3,(H,34,42)(H,35,39)(H,36,45)(H,37,43)(H,38,44)(H,40,41)(H4,30,31,32)/t17-,18-,19-,22+/m0/s1

Standard InChI Key:  SXIKNOJEFQXCPA-ZVVDCOBXSA-N

Molfile:  

 
     RDKit          2D

 45 47  0  0  0  0  0  0  0  0999 V2000
    6.5871  -16.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2948  -16.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0025  -16.9794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2948  -15.7536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7102  -16.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4179  -16.9794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7102  -15.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4179  -15.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0025  -15.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1207  -18.5313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1256  -16.5708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8793  -16.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5871  -17.7966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8793  -18.2052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8793  -19.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1716  -17.7966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1716  -19.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5881  -19.4295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8404  -20.2068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6396  -20.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2933  -20.8139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1867  -19.7699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9859  -19.9402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5330  -19.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2382  -20.7174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3322  -19.5033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8793  -18.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6786  -19.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2256  -18.4593    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0249  -18.6296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5719  -18.0225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2771  -19.4068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4639  -19.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7562  -19.4310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4639  -18.2052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8793  -15.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5385  -15.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2860  -14.4975    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2163  -15.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4712  -14.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9271  -13.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1280  -14.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8760  -14.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4218  -15.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1811  -13.1154    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  6
  7  8  1  0
  7  9  1  0
  6 10  1  0
  6 11  2  0
  1 12  1  1
  1 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 17  1  1
 15 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  1  1
 24 10  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 17 33  1  0
 33 34  1  0
 33 35  2  0
 12 36  1  0
 36 37  2  0
 37 38  1  0
 38 40  1  0
 39 36  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  2  0
 44 39  1  0
 41 45  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4791029

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 692.57

Molecular Weight (Monoisotopic): 691.2078

AlogP: -1.06

#Rotatable Bonds: 9

Polar Surface Area: 260.49

Molecular Species: ZWITTERION

HBA: 7

HBD: 10

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 11

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.97

CX Basic pKa: 11.91

CX LogP: -3.04

CX LogD: -3.04

Aromatic Rings: 2

Heavy Atoms: 45

QED Weighted: 0.09

Np Likeness Score: 0.99

References

1. Kemker I,Schröder DC,Feiner RC,Müller KM,Marion A,Sewald N.  (2021)  Tuning the Biological Activity of RGD Peptides with Halotryptophans†.,  64  (1.0): [PMID:33356253] [10.1021/acs.jmedchem.0c01536]

Source

Source(1):

• Scientific Literature