(3S,6R,9S,12R,15S,18R)-3,9-Di-sec-butyl-4,6,10,12,15,16,18-heptamethyl-1,7,13-trioxa-4,10,16-triaza-cyclooctadecane-2,5,8,11,14,17-hexaone

ID: ALA113117

PubChem CID: 9937575

Max Phase: Preclinical

Molecular Formula: C27H45N3O9

Molecular Weight: 555.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)[C@H]1C(=O)O[C@H](C)C(=O)N(C)[C@@H](C)C(=O)O[C@H](C)C(=O)N(C)[C@@H](C(C)CC)C(=O)O[C@H](C)C(=O)N1C

Standard InChI:  InChI=1S/C27H45N3O9/c1-12-14(3)20-26(35)38-17(6)22(31)28(9)16(5)25(34)37-18(7)23(32)29(10)21(15(4)13-2)27(36)39-19(8)24(33)30(20)11/h14-21H,12-13H2,1-11H3/t14?,15?,16-,17+,18+,19+,20-,21-/m0/s1

Standard InChI Key:  UFEYLNCFHINWFJ-ZKVHITAGSA-N

Molfile:  

     RDKit          2D

 39 39  0  0  1  0  0  0  0  0999 V2000
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    6.1917   -3.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -0.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -4.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -1.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -4.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -4.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -2.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -1.6125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -2.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -5.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -1.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042   -3.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -4.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792    0.4500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -0.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542   -2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -2.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -3.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -1.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0542    0.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -0.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042   -1.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -5.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -5.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3417   -2.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6167   -4.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042   -4.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3417   -2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
  3 15  1  0
  4 13  1  0
  5 12  1  0
  6  1  1  0
  7 16  1  0
  8  3  1  0
  9 14  1  0
 10  4  1  0
 11  5  1  0
 12  1  1  0
 13  2  1  0
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 19  5  2  0
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 25  1  1  0
 26  2  1  0
 12 27  1  6
 13 28  1  6
 29  3  1  0
 15 30  1  6
 18 31  1  1
 17 32  1  1
 16 33  1  1
 34 27  1  0
 35 28  1  0
 36 28  1  0
 37 27  1  0
 38 34  1  0
 39 35  1  0
 10 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA113117

   cyclo[N(Me)Ala-D-OAla-N(Me)xiIle-D-OAla-N(Me)xiIle-D-OAla]

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: 555.67

Molecular Weight (Monoisotopic): 555.3156

AlogP: 1.39

#Rotatable Bonds: 4

Polar Surface Area: 139.83

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.30

CX LogD: 2.30

Aromatic Rings: ┄

Heavy Atoms: 39

QED Weighted: 0.37

Np Likeness Score: 0.80

References

1. Jeschke P, Benet-Buchholz J, Harder A, Etzel W, Schindler M, Thielking G..  (2003)  Synthesis and anthelmintic activity of cyclohexadepsipeptides with (S,S,S,R,S,R)-configuration.,  13  (19): [PMID:12951110] [10.1016/s0960-894x(03)00688-7]

2. Jeschke P, Benet-Buchholz J, Harder A, Etzel W, Schindler M, Gau W, Weiss HC..  (2006)  Synthesis and anthelmintic activity of substituted (R)-phenyllactic acid containing cyclohexadepsipeptides.,  16  (16): [PMID:16781154] [10.1016/j.bmcl.2006.05.040]

Source

Source(1):

• Scientific Literature