7-(4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,9,11-trihydroxy-9-(2-hydroxy-ethyl)-7,8,9,10-tetrahydro-naphthacene-5,12-dione hydrochloride

ID: ALA538509

PubChem CID: 45264672

Max Phase: Preclinical

Molecular Formula: C26H30ClNO9

Molecular Weight: 499.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1OC(O[C@H]2C[C@](O)(CCO)Cc3c(O)c4c(c(O)c32)C(=O)c2ccccc2C4=O)CC(N)C1O.Cl

Standard InChI:  InChI=1S/C26H29NO9.ClH/c1-11-21(29)15(27)8-17(35-11)36-16-10-26(34,6-7-28)9-14-18(16)25(33)20-19(24(14)32)22(30)12-4-2-3-5-13(12)23(20)31;/h2-5,11,15-17,21,28-29,32-34H,6-10,27H2,1H3;1H/t11?,15?,16-,17?,21?,26-;/m0./s1

Standard InChI Key:  WJKDXXOITSVSKQ-FIHNZLEFSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
    9.6129   -2.7602    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.6089    0.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6089   -1.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9070   -2.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9070    0.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9711   -1.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9711    0.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6891   -2.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6891    0.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2050    0.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2691   -2.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5637   -4.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5628   -5.7738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8633   -3.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1609   -5.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2660   -3.5199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2691    0.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9070   -3.0191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9070    2.1935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6923    2.1935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6918   -3.0191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0282   -3.7761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8254   -0.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1997   -6.3762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5439    1.4241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5030    0.9935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5030   -2.0191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8532   -2.6617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8606   -7.7247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8176   -2.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8010    0.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8010   -1.2660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  2  5  1  0
  6  7  1  0
  3  8  1  0
  6  8  2  0
  2  9  1  0
  7  9  2  0
  5 10  1  0
  4 11  1  0
 10 11  1  0
  6 12  1  0
 13 14  1  0
 13 15  1  0
 15 17  1  0
 16 17  1  0
 14 18  1  0
 16 18  1  0
 12 20  1  0
 19 20  1  0
 12 21  1  6
 13 21  1  0
  7 22  1  0
 19 22  1  0
  4 23  2  0
  5 24  2  0
  9 25  1  0
  8 26  1  0
 17 27  1  0
 19 28  1  0
 16 29  1  0
 19 30  1  6
 10 31  2  0
 11 32  2  0
 18 34  1  0
 28 35  1  0
 33 35  1  0
 31 36  1  0
 32 37  1  0
 36 37  2  0
M  END

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: 499.52

Molecular Weight (Monoisotopic): 499.1842

AlogP: 0.81

#Rotatable Bonds: 4

Polar Surface Area: 179.77

Molecular Species: BASE

HBA: 10

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.24

CX Basic pKa: 9.40

CX LogP: 0.82

CX LogD: 0.13

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.28

Np Likeness Score: 1.72

References

1. Adams N, Blake C, Broadhurst MJ, Bushnell DJ, Hassall CH, Hartmann HR, Keech E, Stratton AR, Thomas GJ..  (1990)  Synthesis and antitumor activity of novel 4-demethoxyanthracyclines.,  33  (9): [PMID:2391681] [10.1021/jm00171a010]

Source

Source(1):

• Scientific Literature