5-beta-fluoroethylaminocamptothecin

ID: ALA220666

PubChem CID: 44420366

Max Phase: Preclinical

Molecular Formula: C22H20FN3O4

Molecular Weight: 409.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 5-Beta-Flouroethylaminocamptothecin | CHEMBL220666|5-beta-flouroethylaminocamptothecin

Canonical SMILES:  CC[C@@]1(O)C(=O)OCc2c1c(NCCF)c1n(c2=O)Cc2cc3ccccc3nc2-1

Standard InChI:  InChI=1S/C22H20FN3O4/c1-2-22(29)16-14(11-30-21(22)28)20(27)26-10-13-9-12-5-3-4-6-15(12)25-17(13)19(26)18(16)24-8-7-23/h3-6,9,24,29H,2,7-8,10-11H2,1H3/t22-/m0/s1

Standard InChI Key:  XCZGVGKDNSYIMT-QFIPXVFZSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  1  0  0  0  0  0999 V2000
    4.2532  -11.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2523  -12.0518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9293  -12.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9276  -10.8770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6052  -11.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6059  -12.0478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2835  -12.4371    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2782  -10.8723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9562  -11.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9592  -12.0457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5624  -10.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2409  -11.2053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2382  -12.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9551  -12.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9564  -10.7922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6738  -11.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6751  -12.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3947  -12.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1136  -12.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1083  -11.1964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3879  -10.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9760  -13.0322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8078  -13.0284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0163  -13.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8354  -12.4435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9554   -9.9649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9543  -13.2804    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2362  -13.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5189  -13.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8008  -13.6927    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  2  0
 14 17  1  0
  6  7  1  0
 16 15  1  0
 15 12  1  0
  7 10  2  0
  1  2  2  0
 16 17  2  0
  9  8  2  0
 17 18  1  0
  8  5  1  0
 18 19  1  0
  9 10  1  0
 19 20  1  0
  5  4  2  0
 20 21  1  0
 21 16  1  0
  4  1  1  0
 18 22  1  1
 18 23  1  0
 10 13  1  0
 23 24  1  0
 12 11  1  0
 19 25  2  0
 11  9  1  0
 15 26  2  0
  2  3  1  0
 14 27  1  0
  5  6  1  0
 27 28  1  0
 12 13  1  0
 28 29  1  0
  3  6  2  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA220666

   5-beta-Flouroethylaminocamptothecin

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: 409.42

Molecular Weight (Monoisotopic): 409.1438

AlogP: 2.46

#Rotatable Bonds: 4

Polar Surface Area: 93.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.64

CX Basic pKa: 1.80

CX LogP: 0.82

CX LogD: 0.82

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: 0.25

References

1. Torregrossa J, Bubley GJ, Jones GB..  (2006)  Microwave expedited synthesis of 5-aminocamptothecin analogs: Inhibitors of hypoxia inducible factor HIF-1alpha.,  16  (23): [PMID:16971123] [10.1016/j.bmcl.2006.08.103]

Source

Source(1):

• Scientific Literature