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

ID: ALA2094055

PubChem CID: 70695542

Max Phase: Preclinical

Molecular Formula: C26H30ClNO8

Molecular Weight: 483.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@@]1(O)Cc2c(O)c3c(c(O)c2[C@@H](O[C@H]2C[C@H](N)[C@H](O)[C@H](C)O2)C1)C(=O)c1ccccc1C3=O.Cl

Standard InChI:  InChI=1S/C26H29NO8.ClH/c1-3-26(33)9-14-18(16(10-26)35-17-8-15(27)21(28)11(2)34-17)25(32)20-19(24(14)31)22(29)12-6-4-5-7-13(12)23(20)30;/h4-7,11,15-17,21,28,31-33H,3,8-10,27H2,1-2H3;1H/t11-,15-,16-,17-,21+,26+;/m0./s1

Standard InChI Key:  MUOZORTYCZNOHJ-SYJISJPASA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -4.6172    3.2553    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  -12.3400    4.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0545    5.0768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7689    4.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7690    3.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0545    3.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.6255    5.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9110    4.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9110    3.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6255    3.4269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1965    5.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4821    4.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4821    3.8394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.6255    5.9019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1965    2.6019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1965    5.9019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6406    5.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3386    4.2519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7676    2.6019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1842    2.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3977    1.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8144    0.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0175    0.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8040    1.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3873    2.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0279   -0.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4341    0.2684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0071    1.8622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8156    5.3789    0.0000 C   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
 11 20  2  0
  8 21  2  0
 15 22  1  0
 12 23  1  0
 17 24  1  0
 17 25  1  1
 19 26  1  6
 27 26  1  1
 27 28  1  0
 32 27  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 29 33  1  6
 30 34  1  6
 31 35  1  6
 24 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: 483.52

Molecular Weight (Monoisotopic): 483.1893

AlogP: 1.84

#Rotatable Bonds: 3

Polar Surface Area: 159.54

Molecular Species: BASE

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.24

CX Basic pKa: 9.40

CX LogP: 2.33

CX LogD: 1.64

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.35

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