4-(4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-2-carboxylic acid benzylamide hydrochloride

ID: ALA554991

PubChem CID: 45264626

Max Phase: Preclinical

Molecular Formula: C32H33ClN2O9

Molecular Weight: 588.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1OC(O[C@H]2C[C@](O)(C(=O)NCc3ccccc3)Cc3c(O)c4c(c(O)c32)C(=O)c2ccccc2C4=O)CC(N)C1O.Cl

Standard InChI:  InChI=1S/C32H32N2O9.ClH/c1-15-26(35)20(33)11-22(42-15)43-21-13-32(41,31(40)34-14-16-7-3-2-4-8-16)12-19-23(21)30(39)25-24(29(19)38)27(36)17-9-5-6-10-18(17)28(25)37;/h2-10,15,20-22,26,35,38-39,41H,11-14,33H2,1H3,(H,34,40);1H/t15?,20?,21-,22?,26?,32-;/m0./s1

Standard InChI Key:  OQABYNWJVKKJKJ-FKLNMSSASA-N

Molfile:  

     RDKit          2D

 44 48  0  0  0  0  0  0  0  0999 V2000
    8.3423   -0.5189    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
   -3.2050   -1.2660    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
    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
    4.5671   -1.2660    0.0000 C   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
    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
    7.1619   -4.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    5.8030    2.5122    0.0000 N   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
    3.4733    2.2571    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
    5.7365    4.0115    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
   -4.5030   -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
    7.0012    4.8196    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
    6.9369    6.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3313    4.1261    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
    9.5970    4.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2026    7.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5326    6.4298    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
 10 18  1  0
 15 19  1  0
 19 21  1  0
 20 21  1  0
 16 22  1  0
 20 22  1  0
 13 23  1  6
 15 23  1  0
 18 24  1  0
  4 25  2  0
  5 26  2  0
 18 27  2  0
  8 28  1  0
  9 29  1  0
 10 30  1  6
 21 31  1  0
 24 32  1  0
 20 33  1  0
 11 34  2  0
 12 35  2  0
 32 36  1  0
 22 37  1  0
 36 38  2  0
 36 39  1  0
 35 40  1  0
 34 41  1  0
 40 41  2  0
 39 42  2  0
 38 43  1  0
 42 44  1  0
 43 44  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: 588.61

Molecular Weight (Monoisotopic): 588.2108

AlogP: 1.75

#Rotatable Bonds: 5

Polar Surface Area: 188.64

Molecular Species: BASE

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 8.03

CX Basic pKa: 9.32

CX LogP: 2.33

CX LogD: 1.82

Aromatic Rings: 3

Heavy Atoms: 43

QED Weighted: 0.19

Np Likeness Score: 1.06

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