Jadomycin N-epsilon-trifluoroacetyl-L-lysine lactam

ID: ALA4213392

PubChem CID: 145966271

Max Phase: Preclinical

Molecular Formula: C32H31F3N2O10

Molecular Weight: 660.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(O)c2c(c1)C1OC(=O)[C@H](CCCCNC(=O)C(F)(F)F)N1C1=C2C(=O)c2cccc(O[C@H]3C[C@@H](O)[C@@H](O)[C@H](C)O3)c2C1=O

Standard InChI:  InChI=1S/C32H31F3N2O10/c1-13-10-16-22(18(38)11-13)24-25(37-17(30(43)47-29(16)37)7-3-4-9-36-31(44)32(33,34)35)28(42)23-15(27(24)41)6-5-8-20(23)46-21-12-19(39)26(40)14(2)45-21/h5-6,8,10-11,14,17,19,21,26,29,38-40H,3-4,7,9,12H2,1-2H3,(H,36,44)/t14-,17-,19+,21-,26-,29?/m0/s1

Standard InChI Key:  YTNRRHWTGTXECY-DPJKXRGSSA-N

Molfile:  

     RDKit          2D

 47 52  0  0  0  0  0  0  0  0999 V2000
    3.8400   -3.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8388   -4.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5537   -4.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5518   -3.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2672   -3.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2661   -4.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9790   -4.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9813   -3.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6988   -3.5606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6953   -4.3871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4123   -3.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1248   -3.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8409   -3.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8458   -2.3324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1285   -1.9161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4153   -2.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9813   -2.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7020   -1.9122    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5619   -1.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9781   -5.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5554   -5.6274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1234   -4.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4075   -4.8013    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5745   -5.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3936   -5.6988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7328   -4.9478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8024   -6.4155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0192   -6.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2699   -7.0043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7146   -7.6144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9653   -8.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4100   -9.0104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6607   -9.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1054  -10.4065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4667   -9.9723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418   -6.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1285   -5.6341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4170   -6.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4144   -6.8699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1296   -7.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8472   -6.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7032   -5.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6993   -7.2810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1285   -8.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5959  -10.9620    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2403  -10.3598    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.2287  -11.2595    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 10  1  0
  9  8  1  0
  9 10  2  0
  9 11  1  0
 10 23  1  0
 22 12  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  8 17  2  0
 16 18  1  0
 14 19  1  0
  7 20  2  0
  3 21  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 22  1  0
 25 27  2  0
 24 28  1  6
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 33 35  2  0
 36 21  1  1
 36 37  1  0
 36 41  1  0
 37 38  1  0
 38 39  1  0
 39 40  1  0
 40 41  1  0
 38 42  1  6
 39 43  1  1
 40 44  1  1
 34 45  1  0
 34 46  1  0
 34 47  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4213392

   ---

Molecule Features

Natural Product: Yes

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: 660.60

Molecular Weight (Monoisotopic): 660.1931

AlogP: 2.81

#Rotatable Bonds: 7

Polar Surface Area: 171.93

Molecular Species: NEUTRAL

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.54

CX Basic pKa: ┄

CX LogP: 3.33

CX LogD: 3.10

Aromatic Rings: 2

Heavy Atoms: 47

QED Weighted: 0.25

Np Likeness Score: 1.12

References

1. Forget SM, Robertson AW, Overy DP, Kerr RG, Jakeman DL..  (2017)  Furan and Lactam Jadomycin Biosynthetic Congeners Isolated from Streptomyces venezuelae ISP5230 Cultured with Nε-Trifluoroacetyl-l-lysine.,  80  (6): [PMID:28520425] [10.1021/acs.jnatprod.7b00152]

Source

Source(1):

• Scientific Literature