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

ID: ALA122174

Max Phase: Preclinical

Molecular Formula: C26H32N2O8S

Molecular Weight: 532.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCSC[C@H]1c2cccc(O)c2C(=O)C2=C(O)[C@]3(O)C(O)=C(C(N)=O)C(=O)[C@@H](N(C)C)C3[C@@H](O)C21

Standard InChI:  InChI=1S/C26H32N2O8S/c1-4-5-9-37-10-12-11-7-6-8-13(29)14(11)20(30)16-15(12)21(31)18-19(28(2)3)22(32)17(25(27)35)24(34)26(18,36)23(16)33/h6-8,12,15,18-19,21,29,31,33-34,36H,4-5,9-10H2,1-3H3,(H2,27,35)/t12-,15?,18?,19-,21-,26-/m0/s1

Standard InChI Key:  AXVDAFVBOYJDPC-RTBKZBSSSA-N

Molfile:  

     RDKit          2D

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  1 20  1  6
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 34 28  1  0
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 36 35  1  0
 37 36  1  0
  9 12  1  0
  7 10  1  0
 11 13  1  0
 31 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA122174

   ---

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: 532.62

Molecular Weight (Monoisotopic): 532.1879

AlogP: 1.17

#Rotatable Bonds: 7

Polar Surface Area: 181.62

Molecular Species: ACID

HBA: 10

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.81

CX Basic pKa: 5.77

CX LogP: -1.87

CX LogD: -2.87

Aromatic Rings: 1

Heavy Atoms: 37

QED Weighted: 0.22

Np Likeness Score: 1.04

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