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

ID: ALA2094029

PubChem CID: 70695531

Max Phase: Preclinical

Molecular Formula: C25H28ClNO9

Molecular Weight: 485.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1OC(O[C@H]2C[C@](O)(CO)Cc3c(O)c4c(c(O)c32)C(=O)c2ccccc2C4=O)C[C@H](N)[C@@H]1O.Cl

Standard InChI:  InChI=1S/C25H27NO9.ClH/c1-10-20(28)14(26)6-16(34-10)35-15-8-25(33,9-27)7-13-17(15)24(32)19-18(23(13)31)21(29)11-4-2-3-5-12(11)22(19)30;/h2-5,10,14-16,20,27-28,31-33H,6-9,26H2,1H3;1H/t10-,14-,15-,16?,20+,25-;/m0./s1

Standard InChI Key:  QRITYCDHUAXAHH-NYIGVIBTSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   11.6057    0.7589    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6826    0.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6826   -0.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9687   -0.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9687    0.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1016   -0.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1016    0.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3965    0.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3965   -0.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2548    0.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2548   -0.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5294    0.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8155   -0.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8155    0.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5275   -1.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5270   -2.7487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5294   -0.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2422   -1.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9559   -2.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9565   -1.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2412   -3.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8138   -1.5091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9687   -1.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9687    1.6332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3983    1.6332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3980   -1.2336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0905    0.2029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4329   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5272   -3.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5409   -0.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5409    0.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2408   -3.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8271    0.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8271   -0.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9419    1.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7669    1.2647    0.0000 O   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
  5 10  1  0
  4 11  1  0
 10 11  1  0
  6 13  1  0
  7 14  1  0
 12 14  1  0
 15 16  1  0
 12 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
  4 23  2  0
  5 24  2  0
  8 25  1  0
  9 26  1  0
 12 27  1  6
 20 28  1  6
 19 29  1  6
 11 30  2  0
 10 31  2  0
 21 32  1  6
 31 33  1  0
 30 34  1  0
 33 34  2  0
 12 35  1  0
 35 36  1  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: 485.49

Molecular Weight (Monoisotopic): 485.1686

AlogP: 0.42

#Rotatable Bonds: 3

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: 8.23

CX Basic pKa: 9.40

CX LogP: 0.76

CX LogD: 0.08

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.28

Np Likeness Score: 1.64

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