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 phenylamide hydrochloride

ID: ALA553479

PubChem CID: 45264656

Max Phase: Preclinical

Molecular Formula: C31H31ClN2O9

Molecular Weight: 574.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1OC(O[C@H]2C[C@](O)(C(=O)Nc3ccccc3)Cc3c(O)c4c(c(O)c32)C(=O)c2ccccc2C4=O)CC(N)C1O.Cl

Standard InChI:  InChI=1S/C31H30N2O9.ClH/c1-14-25(34)19(32)11-21(41-14)42-20-13-31(40,30(39)33-15-7-3-2-4-8-15)12-18-22(20)29(38)24-23(28(18)37)26(35)16-9-5-6-10-17(16)27(24)36;/h2-10,14,19-21,25,34,37-38,40H,11-13,32H2,1H3,(H,33,39);1H/t14?,19?,20-,21?,25?,31-;/m0./s1

Standard InChI Key:  AVGIGARVIOJRCK-DRCYHWLDSA-N

Molfile:  

     RDKit          2D

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    4.3345    6.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5974    7.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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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: 574.59

Molecular Weight (Monoisotopic): 574.1951

AlogP: 2.07

#Rotatable Bonds: 4

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: 2.62

CX LogD: 2.11

Aromatic Rings: 3

Heavy Atoms: 42

QED Weighted: 0.20

Np Likeness Score: 1.05

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