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

ID: ALA338161

Max Phase: Preclinical

Molecular Formula: C28H36N2O8S

Molecular Weight: 560.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCSC[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/C28H36N2O8S/c1-4-5-6-7-11-39-12-14-13-9-8-10-15(31)16(13)22(32)18-17(14)23(33)20-21(30(2)3)24(34)19(27(29)37)26(36)28(20,38)25(18)35/h8-10,14,17,20-21,23,31,33,35-36,38H,4-7,11-12H2,1-3H3,(H2,29,37)/t14-,17?,20?,21-,23-,28-/m0/s1

Standard InChI Key:  FNOFKXPIODZCGQ-SMHFBFMPSA-N

Molfile:  

     RDKit          2D

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 36 37  1  0
 37 38  1  0
 38 35  1  0
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  9 12  1  0
  7 10  1  0
 11 13  1  0
 31 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA338161

   ---

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: 560.67

Molecular Weight (Monoisotopic): 560.2192

AlogP: 1.95

#Rotatable Bonds: 9

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: -0.98

CX LogD: -1.98

Aromatic Rings: 1

Heavy Atoms: 39

QED Weighted: 0.19

Np Likeness Score: 1.05

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