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

ID: ALA334155

Max Phase: Preclinical

Molecular Formula: C28H28N2O8S

Molecular Weight: 552.61

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](CSc4ccccc4)C3[C@H](O)C12

Standard InChI:  InChI=1S/C28H28N2O8S/c1-30(2)21-20-23(33)17-14(11-39-12-7-4-3-5-8-12)13-9-6-10-15(31)16(13)22(32)18(17)25(35)28(20,38)26(36)19(24(21)34)27(29)37/h3-10,14,17,20-21,23,31-33,36,38H,11H2,1-2H3,(H2,29,37)/t14-,17?,20?,21-,23-,28-/m0/s1

Standard InChI Key:  IBCXTZMHDXWPGW-SMHFBFMPSA-N

Molfile:  

     RDKit          2D

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    4.9792   -0.5667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 10 17  1  6
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 12 26  1  6
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 37 36  2  0
 38 35  1  0
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  9 12  1  0
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 32 31  2  0
 39 38  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA334155

   ---

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: 552.61

Molecular Weight (Monoisotopic): 552.1566

AlogP: 1.27

#Rotatable Bonds: 5

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: 2.49

CX Basic pKa: 6.23

CX LogP: -2.01

CX LogD: -4.30

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.23

Np Likeness Score: 0.90

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