Cyclostreptin

ID: ALA1242194

PubChem CID: 52948907

Max Phase: Preclinical

Molecular Formula: C24H32O5

Molecular Weight: 400.52

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Cyclostreptin | fr182877|CHEMBL1242194|GLXC-25827|(1R,2R,4R,7R,8R,9R,10S,11R,12R,13S,17R,18R)-8,10-Dihydroxy-1,5,9,18-tetramethyl-16,20-dioxahexacyclo[15.3.2.02,13.04,12.07,11.014,19]docosa-5,14(19)-dien-15-one

Canonical SMILES:  CC1=C[C@H]2[C@@H](O)[C@H](C)[C@@H](O)[C@@H]2[C@H]2[C@@H]3C4=C5O[C@](C)(CC[C@@H](OC4=O)[C@H]5C)[C@@H]3C[C@@H]12

Standard InChI:  InChI=1S/C24H32O5/c1-9-7-13-17(21(26)11(3)20(13)25)16-12(9)8-14-18(16)19-22-10(2)15(28-23(19)27)5-6-24(14,4)29-22/h7,10-18,20-21,25-26H,5-6,8H2,1-4H3/t10-,11+,12+,13-,14-,15-,16+,17+,18-,20+,21-,24-/m1/s1

Standard InChI Key:  WMRQHSFWMFGIFW-SGNBTFORSA-N

Molfile:  

     RDKit          2D

 36 41  0  0  0  0  0  0  0  0999 V2000
   -2.9167    0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9167    0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4926    0.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2046    1.3958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4926    0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2044   -0.2546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2062   -1.0709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4980   -1.4845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7827   -0.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7901   -1.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0071   -1.3410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0047   -0.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4845   -0.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3038   -0.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6496    0.1496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3442    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1666    0.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3512    1.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427    2.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0205    1.5066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7770    1.3896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7812   -1.2743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7875    0.5750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958   -1.9000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014   -2.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1208    0.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2875   -0.6833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6306   -0.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -1.3917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5696    2.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5708    2.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1101    1.9485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9875    0.8208    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9250    0.1667    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6333    1.3917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 16  1  0
  5  3  1  0
  3 21  2  0
  3  4  1  0
 14 22  1  0
  5  6  2  0
  9 23  1  6
 10 11  1  0
 10 24  1  6
 11 13  1  0
  8 25  1  1
 12  9  1  0
  1 26  1  0
 12 13  1  0
 26 27  1  0
  8 27  1  0
  2 28  1  6
  1  2  1  0
 12 29  1  1
  1  4  1  0
 13 30  1  1
  2  6  1  0
 19 31  1  1
 12 16  1  0
 20 32  1  6
 13 14  1  0
 18 33  1  6
 14 15  2  0
 17 34  1  1
 15 17  1  0
 16 35  1  6
 16 17  1  0
  1 36  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1242194

   CYCLOSTREPTIN

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: 400.52

Molecular Weight (Monoisotopic): 400.2250

AlogP: 2.82

#Rotatable Bonds: ┄

Polar Surface Area: 75.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.55

CX LogD: 1.55

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: 2.96

References

1. Buey RM, Calvo E, Barasoain I, Pineda O, Edler MC, Matesanz R, Cerezo G, Vanderwal CD, Day BW, Sorensen EJ, López JA, Andreu JM, Hamel E, Díaz JF..  (2007)  Cyclostreptin binds covalently to microtubule pores and lumenal taxoid binding sites.,  3  (2): [PMID:17206139] [10.1038/nchembio853]

2. Prasher P, Sharma M..  (2019)  Tailored therapeutics based on 1,2,3-1H-triazoles: a mini review.,  10  (8): [PMID:31534652] [10.1039/C9MD00218A]

Source

Source(1):

• Scientific Literature