7-(4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,9,11-trihydroxy-9-(1-hydroxy-ethyl)-7,8,9,10-tetrahydro-naphthacene-5,12-dione hydrochloride

ID: ALA2093883

PubChem CID: 70684981

Max Phase: Preclinical

Molecular Formula: C26H30ClNO9

Molecular Weight: 499.52

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H29NO9.ClH/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31;/h3-6,10-11,15-17,21,28-29,32-34H,7-9,27H2,1-2H3;1H/t10-,11-,15+,16-,17-,21+,26-;/m0./s1

Standard InChI Key:  RTVPMGKHFJTFLA-KNOAOLHUSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
   -0.1179    2.4455    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.2409    3.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9553    4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6698    3.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6698    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9554    2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2409    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5264    4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8119    3.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8119    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5264    2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0974    4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3829    3.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3830    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0974    2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6685    4.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540    3.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540    2.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6685    2.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6685    1.5911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540    1.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540    0.3536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2395   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5250    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5250    1.1786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2395    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2395   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8106   -0.0589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8106    1.5911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5415    4.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1290    3.6536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0974    1.5911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0974    4.8911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5264    4.8911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5264    1.5911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7165    4.3681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9540    5.0826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
 11  7  1  0
  7  2  2  0
  2  8  1  0
  8  9  1  0
 10 11  1  0
  9 12  1  0
 10  9  2  0
 15 10  1  0
 12 13  2  0
 14 15  2  0
 19 14  1  0
 14 13  1  0
 13 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 21 20  1  1
 21 22  1  0
 26 21  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 23 27  1  6
 24 28  1  6
 25 29  1  1
 17 30  1  0
 17 31  1  6
 15 32  1  0
 12 33  1  0
  8 34  2  0
 11 35  2  0
 30 36  1  0
 30 37  1  1
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: 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: 1.18

CX LogD: 0.49

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.28

Np Likeness Score: 1.62

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]

2. 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]

3. 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