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

ID: ALA333888

Max Phase: Preclinical

Molecular Formula: C27H34N2O8S

Molecular Weight: 546.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CCSC[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/C27H34N2O8S/c1-11(2)8-9-38-10-13-12-6-5-7-14(30)15(12)21(31)17-16(13)22(32)19-20(29(3)4)23(33)18(26(28)36)25(35)27(19,37)24(17)34/h5-7,11,13,16,19-20,22,30,32,34-35,37H,8-10H2,1-4H3,(H2,28,36)/t13-,16?,19?,20-,22-,27-/m0/s1

Standard InChI Key:  ACIHDBXDAVSHPZ-LORFFOPBSA-N

Molfile:  

     RDKit          2D

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   11.0125   -6.3917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5917   -5.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3042   -3.8792    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -7.6042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6042   -3.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1625   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 20  1  6
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 27 13  2  0
 28 26  1  0
 29 19  1  0
 30 27  1  0
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 33 16  1  0
 34 28  1  0
 35 36  1  0
 36 34  1  0
 37 35  1  0
 38 35  1  0
  9 12  1  0
  7 10  1  0
 11 13  1  0
 31 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA333888

   ---

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: 546.64

Molecular Weight (Monoisotopic): 546.2036

AlogP: 1.41

#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: -1.59

CX LogD: -2.59

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.22

Np Likeness Score: 1.01

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