[Gly6, Gly7] Polymyxin B3

ID: ALA1077565

PubChem CID: 25232479

Max Phase: Preclinical

Molecular Formula: C44H82N16O13

Molecular Weight: 1043.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC(=O)N[C@@H](CCN)C(=O)N[C@H](C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)CNC(=O)CNC(=O)[C@H](CCN)NC1=O)[C@@H](C)O

Standard InChI:  InChI=1S/C44H82N16O13/c1-4-5-6-7-8-9-32(63)53-28(12-18-47)41(70)60-36(25(3)62)44(73)58-29(13-19-48)39(68)57-31-15-21-50-43(72)35(24(2)61)59-42(71)30(14-20-49)56-38(67)27(11-17-46)54-34(65)23-51-33(64)22-52-37(66)26(10-16-45)55-40(31)69/h24-31,35-36,61-62H,4-23,45-49H2,1-3H3,(H,50,72)(H,51,64)(H,52,66)(H,53,63)(H,54,65)(H,55,69)(H,56,67)(H,57,68)(H,58,73)(H,59,71)(H,60,70)/t24-,25-,26+,27+,28+,29+,30+,31+,35+,36+/m1/s1

Standard InChI Key:  VDKFGINLORKBBM-IJAPUWTDSA-N

Molfile:  

     RDKit          2D

 74 74  0  0  0  0  0  0  0  0999 V2000
    9.3622  -10.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0744  -10.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6459  -10.5586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6459   -9.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9337   -9.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8508   -7.7856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1375   -7.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4242   -7.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7109   -7.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9976   -7.7768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842   -7.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709   -7.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1424   -7.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409   -6.5378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5705   -7.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2833   -7.7709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5689   -6.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2846   -6.1217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2849   -8.5998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9990   -7.3573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7161   -7.7726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4317   -7.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7176   -8.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4302   -6.5300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8607   -7.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5736   -7.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8592   -6.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5748   -6.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5751   -8.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2892   -7.3554    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0064   -7.7664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4144   -7.0460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2389   -7.0388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9921   -6.3354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9458   -7.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6639   -7.0403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3785   -7.4557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6674   -6.2157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0857   -7.0351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8055   -7.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8167   -8.2627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5140   -7.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2256   -7.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3622  -11.7998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7907  -10.9752    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5071  -10.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2235  -10.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5071   -9.7341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2235  -11.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9356  -10.5586    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6520  -10.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3641  -10.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6520  -11.7998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0805  -10.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3641   -9.7341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0805   -9.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7969   -9.7341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0805  -11.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9465   -8.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4871  -12.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4871  -13.0753    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9820   -9.0237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4549   -9.0209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6834   -8.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4194   -8.2771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0732   -9.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8091   -9.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3363   -9.2840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0693  -11.4079    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8572   -7.7744    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2830   -5.2971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1464   -7.7710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5733   -5.2910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7969  -12.2121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
 15 17  1  1
 17 18  1  0
 16 19  2  0
 16 20  1  0
 21 20  1  6
 21 22  1  0
 21 23  1  0
 22 24  2  0
 25 26  1  0
 25 27  1  1
 27 28  1  0
 26 29  2  0
 26 30  1  0
 31 30  1  6
 31  5  1  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 33 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  2  0
 37 39  1  0
 39 40  1  0
 40 41  2  0
 40 42  1  0
 42 43  1  0
  1 44  2  0
  2 45  1  0
 45 46  1  0
 46 47  1  0
 46 48  2  0
 47 49  1  1
 47 50  1  0
 50 51  1  0
 51 52  1  0
 51 53  2  0
 52 54  1  1
 52 55  1  0
 55 56  1  0
 56 57  2  0
 43 56  1  0
 54 58  1  0
 35 59  1  6
 49 60  1  0
  1  2  1  0
 60 61  1  0
  1  3  1  0
 23 62  1  6
  3  4  1  0
 23 63  1  0
  4  5  1  0
 59 64  1  0
  6  7  1  0
 64 65  1  0
  7  8  1  0
  2 66  1  0
  8  9  1  0
 66 67  1  6
  9 10  1  0
 66 68  1  0
 10 11  1  0
  2 69  1  1
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 70  1  0
 70 15  1  0
 22 72  1  0
 72 25  1  0
 28 73  1  0
 18 71  1  0
 58 74  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1077565

   octanoyl-Dab-Thr-Dab-Dab(1)-Dab-Gly-Gly-Dab-Dab-Thr-(1)

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: 1043.24

Molecular Weight (Monoisotopic): 1042.6247

AlogP: ┄

#Rotatable Bonds: ┄

Polar Surface Area: ┄

Molecular Species: ┄

HBA: ┄

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

Aromatic Rings: ┄

Heavy Atoms: ┄

QED Weighted: ┄

Np Likeness Score: ┄

References

1. Velkov T, Thompson PE, Nation RL, Li J..  (2010)  Structure--activity relationships of polymyxin antibiotics.,  53  (5): [PMID:19874036] [10.1021/jm900999h]

Source

Source(1):

• Scientific Literature