6-(3,4-Dichloro-benzylsulfanylmethyl)-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: ALA338028

Max Phase: Preclinical

Molecular Formula: C29H28Cl2N2O8S

Molecular Weight: 635.52

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](CSCc4ccc(Cl)c(Cl)c4)C3[C@H](O)C12

Standard InChI:  InChI=1S/C29H28Cl2N2O8S/c1-33(2)22-21-24(36)18-13(10-42-9-11-6-7-14(30)15(31)8-11)12-4-3-5-16(34)17(12)23(35)19(18)26(38)29(21,41)27(39)20(25(22)37)28(32)40/h3-8,13,18,21-22,24,34-36,39,41H,9-10H2,1-2H3,(H2,32,40)/t13-,18?,21?,22-,24-,29-/m0/s1

Standard InChI Key:  QDMKGDGMISSWPG-XIXJTSLDSA-N

Molfile:  

     RDKit          2D

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    1.3375   -4.3042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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  9 12  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA338028

   ---

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: 635.52

Molecular Weight (Monoisotopic): 634.0943

AlogP: 2.72

#Rotatable Bonds: 6

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: 2.56

CX Basic pKa: 6.20

CX LogP: -0.55

CX LogD: -2.91

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.26

Np Likeness Score: 0.54

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