Jadomycin N-epsilon-trifluoroacetyl-L-lysine

ID: ALA4208463

PubChem CID: 145965614

Max Phase: Preclinical

Molecular Formula: C32H31F3N2O11

Molecular Weight: 676.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(O)c2c3c(n([C@@H](CCCCNC(=O)C(F)(F)F)C(=O)O)c(=O)c2c1)C(=O)c1c(O[C@H]2C[C@@H](O)[C@@H](O)[C@H](C)O2)cccc1C3=O

Standard InChI:  InChI=1S/C32H31F3N2O11/c1-13-10-16-22(18(38)11-13)24-25(37(29(16)43)17(30(44)45)7-3-4-9-36-31(46)32(33,34)35)28(42)23-15(27(24)41)6-5-8-20(23)48-21-12-19(39)26(40)14(2)47-21/h5-6,8,10-11,14,17,19,21,26,38-40H,3-4,7,9,12H2,1-2H3,(H,36,46)(H,44,45)/t14-,17-,19+,21-,26-/m0/s1

Standard InChI Key:  SDXAFRYAPJOIMR-VYCTXMELSA-N

Molfile:  

     RDKit          2D

 48 52  0  0  0  0  0  0  0  0999 V2000
    3.5234  -13.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5223  -14.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2370  -14.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2352  -13.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9506  -13.6998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9494  -14.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6623  -14.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6647  -13.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3821  -13.7019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3787  -14.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0956  -13.2894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8082  -13.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5243  -13.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5292  -12.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8120  -12.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0987  -12.4677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6647  -12.4594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3853  -12.0534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2453  -12.0640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6614  -15.7662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2387  -15.7686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8067  -14.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0909  -14.9426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0770  -15.7673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3628  -16.1807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3637  -17.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6497  -17.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6505  -18.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9366  -18.6571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9374  -19.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2235  -19.8953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6523  -19.8938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5251  -16.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8118  -15.7753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1004  -16.1858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0978  -17.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8129  -17.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5307  -17.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3867  -15.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3826  -17.4223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8118  -18.2492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8057  -16.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8354  -16.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5049  -15.7159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5727  -20.2702    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.4162  -19.5887    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.0856  -20.7455    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.5198  -14.9493    0.0000 O   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  6
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
 33 21  1  1
 33 34  1  0
 33 38  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 35 39  1  6
 36 40  1  1
 37 41  1  1
 24 42  1  0
 42 43  2  0
 42 44  1  0
 31 45  1  0
 31 46  1  0
 31 47  1  0
 22 48  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4208463

   ---

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: 676.60

Molecular Weight (Monoisotopic): 676.1880

AlogP: 2.50

#Rotatable Bonds: 9

Polar Surface Area: 201.69

Molecular Species: ACID

HBA: 11

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.61

CX Basic pKa: ┄

CX LogP: 2.65

CX LogD: -1.00

Aromatic Rings: 3

Heavy Atoms: 48

QED Weighted: 0.16

Np Likeness Score: 0.57

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