9-Acetyl-7-(4-amino-5-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione hydrochloride

ID: ALA541306

PubChem CID: 45264654

Max Phase: Preclinical

Molecular Formula: C27H30ClNO9

Molecular Weight: 511.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1C(N)CC(O[C@H]2C[C@](O)(C(C)=O)Cc3c(O)c4c(c(O)c32)C(=O)c2ccccc2C4=O)OC1C.Cl

Standard InChI:  InChI=1S/C27H29NO9.ClH/c1-11-26(35-3)16(28)8-18(36-11)37-17-10-27(34,12(2)29)9-15-19(17)25(33)21-20(24(15)32)22(30)13-6-4-5-7-14(13)23(21)31;/h4-7,11,16-18,26,32-34H,8-10,28H2,1-3H3;1H/t11?,16?,17-,18?,26?,27-;/m0./s1

Standard InChI Key:  HUOUYAOMHPTADT-WDDHFUHDSA-N

Molfile:  

     RDKit          2D

 38 41  0  0  0  0  0  0  0  0999 V2000
    8.3423   -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    0.9935    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
    4.5671    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
    3.2691    0.9935    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
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    5.8614   -6.5247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2660   -3.5199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5383    1.7041    0.0000 C   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
   -1.9070   -3.0191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5028    2.3104    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
    5.5874   -0.4072    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
    8.4586   -6.5295    0.0000 O   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
   -4.5030    0.9935    0.0000 C   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
    5.5810    2.2981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4561   -7.7295    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
   -5.8010    0.2243    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
  2  8  1  0
  7  8  2  0
  3  9  1  0
  6  9  2  0
  4 11  1  0
  5 12  1  0
 11 12  1  0
  6 13  1  0
  7 14  1  0
 10 14  1  0
 15 16  1  0
 10 17  1  0
 13 17  1  0
 15 18  1  0
 18 20  1  0
 19 20  1  0
 16 21  1  0
 19 21  1  0
 13 22  1  6
 15 22  1  0
 10 23  1  0
  5 24  2  0
  4 25  2  0
 23 26  2  0
  8 27  1  0
  9 28  1  0
 10 29  1  6
 20 30  1  0
 19 31  1  0
 11 32  2  0
 12 33  2  0
 21 34  1  0
 23 35  1  0
 31 36  1  0
 32 37  1  0
 33 38  1  0
 37 38  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: 511.53

Molecular Weight (Monoisotopic): 511.1842

AlogP: 1.67

#Rotatable Bonds: 4

Polar Surface Area: 165.61

Molecular Species: BASE

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.02

CX Basic pKa: 9.10

CX LogP: 2.15

CX LogD: 1.73

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.38

Np Likeness Score: 1.71

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