(Z)-2-((S)-6-amino-2-((S)-2-((S)-1-((2R,8S,11S,14S)-14,18-diamino-2-(3-aminopropyl)-11-(hydroxymethyl)-8-methyl-4,7,10,13-tetraoxo-3,6,9,12-tetraazaoctadecane)pyrrolidine-2-carboxamido)-3-(1H-imidazol-4-yl)propanamido)hexanamido)-5-guanidinopent-2-enoic acid

ID: ALA4750287

PubChem CID: 162651227

Max Phase: Preclinical

Molecular Formula: C42H73N17O11

Molecular Weight: 992.15

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)[C@H](CO)NC(=O)[C@@H](N)CCCCN)C(=O)NCC(=O)N[C@H](CCCN)C(=O)N1CCC[C@H]1C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](CCCCN)C(=O)N/C(=C\CCNC(=N)N)C(=O)O

Standard InChI:  InChI=1S/C42H73N17O11/c1-24(53-38(66)31(22-60)58-35(63)26(46)9-2-4-14-43)34(62)51-21-33(61)54-28(11-6-16-45)40(68)59-18-8-13-32(59)39(67)57-30(19-25-20-49-23-52-25)37(65)55-27(10-3-5-15-44)36(64)56-29(41(69)70)12-7-17-50-42(47)48/h12,20,23-24,26-28,30-32,60H,2-11,13-19,21-22,43-46H2,1H3,(H,49,52)(H,51,62)(H,53,66)(H,54,61)(H,55,65)(H,56,64)(H,57,67)(H,58,63)(H,69,70)(H4,47,48,50)/b29-12-/t24-,26-,27-,28+,30-,31-,32-/m0/s1

Standard InChI Key:  GXTRJPVXZVTEHR-HYLGZJFOSA-N

Molfile:  

 
     RDKit          2D

 70 71  0  0  0  0  0  0  0  0999 V2000
    3.9375  -15.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230  -15.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5085  -15.7709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6519  -15.3583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3664  -15.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0809  -15.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7954  -15.7709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5099  -15.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2243  -15.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9388  -15.3583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6533  -15.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3677  -15.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0822  -15.7709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7966  -15.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5111  -15.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2256  -15.3583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9805  -15.6894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5325  -15.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1199  -14.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3131  -14.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2230  -14.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375  -14.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375  -13.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6519  -12.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6519  -12.0583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375  -16.5959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0809  -14.5333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2243  -16.5959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3677  -14.5333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5111  -16.5958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3664  -16.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0809  -17.0083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5099  -14.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7966  -14.5333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5111  -14.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5111  -13.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2256  -12.8833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9750  -16.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2578  -16.9202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6867  -16.9297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4039  -16.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1156  -16.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4094  -15.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1266  -15.2893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8772  -15.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4333  -15.0179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0255  -14.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2175  -14.4669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1101  -17.7642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8328  -16.5316    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5445  -16.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2617  -16.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9734  -16.9583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2672  -15.7160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5390  -17.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8218  -18.1815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8162  -19.0065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0991  -19.4142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0936  -20.2391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6906  -16.5506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4023  -16.9679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1196  -16.5601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3968  -17.7928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6961  -15.7256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9844  -15.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9899  -14.4834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7071  -14.0756    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7127  -13.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4298  -12.8429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0009  -12.8335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  1  0
  5  4  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
  2 21  1  1
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  1 26  2  0
  6 27  2  0
  9 28  2  0
 12 29  2  0
 15 30  2  0
  5 31  1  6
 31 32  1  0
  8 33  1  1
 14 34  1  6
 34 35  1  0
 35 36  1  0
 36 37  1  0
 17 38  1  1
 38 39  2  0
 38 40  1  0
 40 41  1  0
 41 42  1  0
 41 43  1  1
 43 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  1  0
 47 48  2  0
 48 44  1  0
 42 49  2  0
 42 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  1  0
 52 54  2  0
 51 55  1  6
 55 56  1  0
 56 57  1  0
 57 58  1  0
 58 59  1  0
 53 60  1  0
 60 61  1  0
 61 62  1  0
 61 63  2  0
 60 64  2  0
 64 65  1  0
 65 66  1  0
 66 67  1  0
 67 68  1  0
 68 69  2  0
 68 70  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4750287

   ---

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: 992.15

Molecular Weight (Monoisotopic): 991.5675

AlogP: -6.22

#Rotatable Bonds: 33

Polar Surface Area: 476.20

Molecular Species: ZWITTERION

HBA: 16

HBD: 17

#RO5 Violations: 3

HBA (Lipinski): 28

HBD (Lipinski): 22

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.74

CX Basic pKa: 11.63

CX LogP: -10.40

CX LogD: -18.43

Aromatic Rings: 1

Heavy Atoms: 70

QED Weighted: 0.01

Np Likeness Score: 0.14

References

1. Loza E,Sarciaux M,Ikaunieks M,Katkevics M,Kukosha T,Trufilkina N,Ryabova V,Shubin K,Pantel L,Serri M,Huseby DL,Cao S,Yadav K,Hjort K,Hughes D,Gualtieri M,Suna E,Racine E.  (2020)  Structure-activity relationship studies on the inhibition of the bacterial translation of novel Odilorhabdins analogues.,  28  (11): [PMID:32279921] [10.1016/j.bmc.2020.115469]

Source

Source(1):

• Scientific Literature