[D-Ala6, Ala7] Polymyxin B3

ID: ALA1091292

PubChem CID: 25232308

Max Phase: Preclinical

Molecular Formula: C46H86N16O13

Molecular Weight: 1071.29

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)[C@H](C)NC(=O)[C@@H](C)NC(=O)[C@H](CCN)NC1=O)[C@@H](C)O

Standard InChI:  InChI=1S/C46H86N16O13/c1-6-7-8-9-10-11-34(65)55-28(12-18-47)43(72)62-36(27(5)64)46(75)60-31(15-21-50)41(70)59-33-17-23-52-45(74)35(26(4)63)61-44(73)32(16-22-51)58-40(69)30(14-20-49)56-38(67)25(3)53-37(66)24(2)54-39(68)29(13-19-48)57-42(33)71/h24-33,35-36,63-64H,6-23,47-51H2,1-5H3,(H,52,74)(H,53,66)(H,54,68)(H,55,65)(H,56,67)(H,57,71)(H,58,69)(H,59,70)(H,60,75)(H,61,73)(H,62,72)/t24-,25+,26-,27-,28+,29+,30+,31+,32+,33+,35+,36+/m1/s1

Standard InChI Key:  FDIWXCYNLBBHOI-VPGYKLSSSA-N

Molfile:  

     RDKit          2D

 76 76  0  0  0  0  0  0  0  0999 V2000
   10.6725  -12.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3860  -12.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9565  -12.2705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9565  -11.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2473  -11.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5200   -9.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8046   -9.0895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0934   -9.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3821   -9.0860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6710   -9.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0444   -9.0801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7557   -9.4891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4668   -9.0767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4687   -8.2560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8916   -9.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6021   -9.4847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8891   -8.2494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6039   -7.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6044  -10.3122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0308   -9.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7455   -9.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0332  -10.3096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7432   -8.2470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1754   -9.0763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8858   -9.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1729   -8.2446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8878   -7.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8883  -10.3074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6006   -9.0722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3179   -9.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7236   -8.7603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5484   -8.7533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3041   -8.0535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2538   -9.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9726   -8.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6859   -9.1730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9781   -7.9309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3917   -8.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1129   -9.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3851   -7.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1219   -9.9790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8210   -8.7318    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5295   -9.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2479   -8.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6725  -13.5104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0977  -12.6854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8137  -12.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5297  -12.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8137  -11.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5297  -13.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2391  -12.2705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9593  -12.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6686  -12.2705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9593  -13.5104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3845  -12.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6686  -11.4455    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3845  -11.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1005  -11.4455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3845  -13.5104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2551   -9.9909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7954  -13.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2957  -10.7358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9901  -10.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3844  -11.4224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0965  -11.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6662  -11.0110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3860  -13.0961    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1799   -9.4916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6054   -7.0164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3176   -9.0741    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4599   -9.4870    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8898   -7.0115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1038  -13.9256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7947  -14.7828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7727  -10.7380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7282   -9.9930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 15 16  1  0
 15 17  1  1
 17 18  1  0
 16 19  2  0
 20 21  1  0
 20 22  1  0
 21 23  2  0
 24 25  1  0
 24 26  1  1
 26 27  1  0
 25 28  2  0
 25 29  1  0
 30 29  1  6
 30  5  1  0
 30 31  1  0
 31 32  1  0
 31 33  2  0
 32 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
 36 38  1  0
 38 39  1  0
 38 40  1  6
 39 41  2  0
 39 42  1  0
 42 43  1  0
 43 44  1  1
  1 45  2  0
  2 46  1  0
 46 47  1  0
 47 48  1  0
 47 49  2  0
 48 50  1  1
 48 51  1  0
 51 52  1  0
 52 53  1  0
 52 54  2  0
 53 55  1  1
 53 56  1  0
 56 57  1  0
 57 58  2  0
 43 57  1  0
 55 59  1  0
 34 60  1  6
 50 61  1  0
 22 62  1  6
 60 63  1  0
  2 64  1  0
 64 65  1  6
 64 66  1  0
  2 67  1  1
  1  2  1  0
  1  3  1  0
  3  4  1  0
  4  5  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 18 69  1  0
 27 72  1  0
 13 68  1  0
 68 15  1  0
 59 73  1  0
 16 70  1  0
 20 70  1  6
 61 74  1  0
 22 75  1  0
 21 71  1  0
 71 24  1  0
 63 76  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1091292

   octanoyl-Dab-Thr-Dab-Dab(1)-Dab-D-Ala-Ala-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: 1071.29

Molecular Weight (Monoisotopic): 1070.6560

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