7-methy-10-hydroxyhomocamptothecin

ID: ALA1096195

PubChem CID: 46887984

Max Phase: Preclinical

Molecular Formula: C22H20N2O5

Molecular Weight: 392.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@]1(O)CC(=O)OCc2c1cc1n(c2=O)Cc2c-1nc1ccc(O)cc1c2C

Standard InChI:  InChI=1S/C22H20N2O5/c1-3-22(28)8-19(26)29-10-15-16(22)7-18-20-14(9-24(18)21(15)27)11(2)13-6-12(25)4-5-17(13)23-20/h4-7,25,28H,3,8-10H2,1-2H3/t22-/m1/s1

Standard InChI Key:  CQYIILFNLODHHN-JOCHJYFZSA-N

Molfile:  

     RDKit          2D

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   -4.3228    0.8558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6082    0.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6100    2.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8946    1.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8939    0.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1788    0.4492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1844    2.1010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4685    1.6937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4654    0.8668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6832    1.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1945    1.2851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6787    0.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3443   -0.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6196    1.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1018    1.8710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4789   -0.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7097   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3399   -0.1101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4767   -1.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2004   -0.9252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0362    2.0955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1888    2.9257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8740   -1.4013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0956   -1.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6886   -1.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9206   -1.8081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
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  1  2  2  0
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 17 18  2  0
  8  5  1  0
 18 19  1  0
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  5  4  2  0
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  4  1  1  0
 20 22  1  0
 21 23  1  0
 22 23  1  0
 10 13  1  0
  1 24  1  0
 12 11  1  0
  8 25  1  0
 11  9  1  0
 23 26  2  0
  2  3  1  0
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  5  6  1  0
 27 28  1  0
 12 13  1  0
 20 29  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA1096195

   (20R)-20-ethyl-7,20-dihydroxy-10-methyl-17-oxa-3,13-diazapentacyclo[11.9.0.02,11.04,9.015,21]docosa-1(22),2(11),3,5,7,9,15(21)-heptaene-14,18-dione

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: 392.41

Molecular Weight (Monoisotopic): 392.1372

AlogP: 2.48

#Rotatable Bonds: 1

Polar Surface Area: 101.65

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.67

CX Basic pKa: 4.02

CX LogP: 1.36

CX LogD: 1.36

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.48

Np Likeness Score: 1.00

References

1. Miao Z, Zhang J, You L, Wang J, Sheng C, Yao J, Zhang W, Feng H, Guo W, Zhou L, Liu W, Zhu L, Cheng P, Che X, Wang W, Luo C, Xu Y, Dong G..  (2010)  Phosphate ester derivatives of homocamptothecin: synthesis, solution stabilities and antitumor activities.,  18  (9): [PMID:20371183] [10.1016/j.bmc.2010.03.039]

Source

Source(1):

• Scientific Literature