2-((2S,5R,8S,11S)-5-((7-(3-aminophenyl)-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: ALA4790959

PubChem CID: 162670788

Max Phase: Preclinical

Molecular Formula: C34H44N10O7

Molecular Weight: 704.79

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)[C@@H]1NC(=O)[C@@H](Cc2c[nH]c3c(-c4cccc(N)c4)cccc23)NC(=O)[C@H](CC(=O)O)NC(=O)CNC(=O)[C@H](CCCNC(=N)N)NC1=O

Standard InChI:  InChI=1S/C34H44N10O7/c1-17(2)28-33(51)42-23(10-5-11-38-34(36)37)30(48)40-16-26(45)41-25(14-27(46)47)31(49)43-24(32(50)44-28)13-19-15-39-29-21(8-4-9-22(19)29)18-6-3-7-20(35)12-18/h3-4,6-9,12,15,17,23-25,28,39H,5,10-11,13-14,16,35H2,1-2H3,(H,40,48)(H,41,45)(H,42,51)(H,43,49)(H,44,50)(H,46,47)(H4,36,37,38)/t23-,24+,25-,28-/m0/s1

Standard InChI Key:  WAJIHESGSSDZLV-GIBNYFNHSA-N

Molfile:  

 
     RDKit          2D

 51 54  0  0  0  0  0  0  0  0999 V2000
   20.9044  -17.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6121  -16.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3198  -17.0702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6121  -15.8444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0275  -16.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7352  -17.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0275  -15.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7352  -15.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3198  -15.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4381  -18.6221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4430  -16.6616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1967  -16.6616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9044  -17.8874    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1967  -18.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1967  -19.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4890  -17.8874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4890  -19.5218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9055  -19.5203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1577  -20.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9570  -20.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6107  -20.9047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5040  -19.8607    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3033  -20.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8503  -19.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5555  -20.8082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6496  -19.5941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1966  -18.9870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9959  -19.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5430  -18.5501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3422  -18.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8893  -18.1133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.5944  -19.4976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.7813  -19.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0736  -19.5218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7813  -18.2960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1967  -15.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8559  -15.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6033  -14.5883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5337  -15.3655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7885  -14.5896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2444  -13.9829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4454  -14.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1933  -14.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7391  -15.5345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4959  -13.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2969  -13.0425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5511  -12.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0052  -11.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2020  -11.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9515  -12.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6542  -11.2226    0.0000 N   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  1
  7  8  1  0
  7  9  1  0
  6 10  1  0
  6 11  2  0
  1 12  1  6
  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
 45 46  2  0
 46 47  1  0
 47 48  2  0
 48 49  1  0
 49 50  2  0
 50 45  1  0
 41 45  1  0
 49 51  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4790959

   ---

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: 704.79

Molecular Weight (Monoisotopic): 704.3394

AlogP: -0.58

#Rotatable Bonds: 10

Polar Surface Area: 286.51

Molecular Species: ZWITTERION

HBA: 8

HBD: 11

#RO5 Violations: 2

HBA (Lipinski): 17

HBD (Lipinski): 13

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.75

CX Basic pKa: 12.76

CX LogP: -2.99

CX LogD: -2.99

Aromatic Rings: 3

Heavy Atoms: 51

QED Weighted: 0.06

Np Likeness Score: 0.89

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