6-Cyclopentylsulfanylmethyl-4-dimethylamino-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide

ID: ALA331492

Max Phase: Preclinical

Molecular Formula: C27H32N2O7S

Molecular Weight: 528.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)[C@@H]1C(=O)C(C(N)=O)=C(O)[C@@]2(O)C(=O)C3=C(O)c4c(O)cccc4[C@H](CSC4CCCC4)C3CC12

Standard InChI:  InChI=1S/C27H32N2O7S/c1-29(2)21-16-10-14-15(11-37-12-6-3-4-7-12)13-8-5-9-17(30)18(13)22(31)19(14)24(33)27(16,36)25(34)20(23(21)32)26(28)35/h5,8-9,12,14-16,21,30-31,34,36H,3-4,6-7,10-11H2,1-2H3,(H2,28,35)/t14?,15-,16?,21-,27-/m0/s1

Standard InChI Key:  OKIUTKPINBNARN-HANPYULSSA-N

Molfile:  

     RDKit          2D

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   11.0750   -6.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -5.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -7.5417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1 21  1  6
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 31 30  2  0
 36 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA331492

   ---

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: 528.63

Molecular Weight (Monoisotopic): 528.1930

AlogP: 2.18

#Rotatable Bonds: 5

Polar Surface Area: 161.39

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.60

CX Basic pKa: 6.60

CX LogP: -1.23

CX LogD: -3.23

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.36

Np Likeness Score: 0.85

References

1. Nelson ML, Park BH, Andrews JS, Georgian VA, Thomas RC, Levy SB..  (1993)  Inhibition of the tetracycline efflux antiport protein by 13-thio-substituted 5-hydroxy-6-deoxytetracyclines.,  36  (3): [PMID:8426364] [10.1021/jm00055a008]

Source

Source(1):

• Scientific Literature