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

ID: ALA2093886

PubChem CID: 70687153

Max Phase: Preclinical

Molecular Formula: C26H28ClNO9

Molecular Weight: 497.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)[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/C26H27NO9.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;/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3;1H/t10-,15+,16-,17-,21-,26-;/m0./s1

Standard InChI Key:  JVHPTYWUBOQMBP-WIFYJJKPSA-N

Molfile:  

     RDKit          2D

 37 40  0  0  0  0  0  0  0  0999 V2000
    4.7875   -0.5880    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3349    0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0488   -1.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488    0.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5100   -2.3505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7963   -1.9359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0488    1.2064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0488   -1.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9265    1.2707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3808    1.2064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3805   -1.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0730   -0.2240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6147   -1.9107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7090   -3.5733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4766   -1.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4766    0.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0904   -4.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0695    1.2639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905    0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905   -0.6963    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  1
 10 23  1  0
  5 24  2  0
  4 25  2  0
 23 26  2  0
  8 27  1  0
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 10 29  1  6
 20 30  1  1
 19 31  1  1
 11 32  2  0
 12 33  2  0
 21 34  1  6
 23 35  1  0
 33 36  1  0
 32 37  1  0
 36 37  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: 497.50

Molecular Weight (Monoisotopic): 497.1686

AlogP: 1.02

#Rotatable Bonds: 3

Polar Surface Area: 176.61

Molecular Species: BASE

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.02

CX Basic pKa: 9.18

CX LogP: 1.51

CX LogD: 1.06

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.33

Np Likeness Score: 1.67

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