Tiancimycin F

ID: ALA4634930

PubChem CID: 156013575

Max Phase: Preclinical

Molecular Formula: C29H21NO10

Molecular Weight: 543.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)[C@H](O)[C@@](C)(O)[C@@]12O[C@]13c1cc(O)c4c(c1N[C@H]2C#C/C=C\C#C[C@H]3O)C(=O)c1cc(O)ccc1C4=O

Standard InChI:  InChI=1S/C29H21NO10/c1-27(38,25(36)26(37)39-2)29-18-7-5-3-4-6-8-19(33)28(29,40-29)16-12-17(32)20-21(22(16)30-18)24(35)15-11-13(31)9-10-14(15)23(20)34/h3-4,9-12,18-19,25,30-33,36,38H,1-2H3/b4-3-/t18-,19+,25-,27+,28-,29+/m0/s1

Standard InChI Key:  SRBWZZOBDMCFHB-XIQYBZFWSA-N

Molfile:  

 
     RDKit          2D

 40 45  0  0  0  0  0  0  0  0999 V2000
   12.0212   -4.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0201   -5.2439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7281   -5.6529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7263   -4.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4349   -4.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4383   -5.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1507   -5.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1439   -4.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8609   -4.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8637   -5.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5783   -5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2906   -5.2324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5686   -4.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2861   -4.4081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2738   -2.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5593   -3.1768    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3134   -4.0159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1394   -3.1858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1532   -6.4705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9913   -3.1682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0142   -3.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2778   -3.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2693   -1.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2613   -1.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2531   -0.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7370   -4.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0059   -0.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1068   -1.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2579   -2.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7013   -2.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4067   -3.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1167   -2.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8221   -3.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5321   -2.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1213   -1.9544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4021   -3.9933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7060   -1.9464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4033   -2.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2339   -5.0068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5821   -6.4651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10 11  1  0
 11 12  2  0
 12 14  1  0
 13  9  1  0
 13 14  2  0
 13 16  1  0
 14 21  1  0
 20 15  1  0
 15 16  1  0
  1 17  1  0
  8 18  2  0
  7 19  2  0
 21 20  1  0
 20 22  1  6
 21 22  1  6
 15 23  1  1
 23 24  3  0
 24 25  1  0
 21 26  1  0
 25 27  2  0
 27 28  1  0
 28 29  3  0
 29 26  1  0
 20 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 32 35  2  0
 31 36  1  6
 30 37  1  6
 30 38  1  0
 26 39  1  1
 11 40  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA4634930

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 543.48

Molecular Weight (Monoisotopic): 543.1165

AlogP: -0.15

#Rotatable Bonds: 3

Polar Surface Area: 186.15

Molecular Species: NEUTRAL

HBA: 11

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.24

CX Basic pKa: ┄

CX LogP: 2.11

CX LogD: 1.72

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.11

Np Likeness Score: 1.85

References

1. Adhikari A, Teijaro CN, Yan X, Chang CY, Gui C, Liu YC, Crnovcic I, Yang D, Annaval T, Rader C, Shen B..  (2020)  Characterization of TnmH as an O-Methyltransferase Revealing Insights into Tiancimycin Biosynthesis and Enabling a Biocatalytic Strategy To Prepare Antibody-Tiancimycin Conjugates.,  63  (15): [PMID:32658465] [10.1021/acs.jmedchem.0c00799]

Source

Source(1):

• Scientific Literature