(6R,7S)-6,7,9,10-tetrahydroxy-7-methyl-2-(piperidin-1-yl)-5,6,7,8-tetrahydroanthracene-1,4-dione

ID: ALA4513475

PubChem CID: 155538924

Max Phase: Preclinical

Molecular Formula: C20H23NO6

Molecular Weight: 373.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C[C@]1(O)Cc2c(O)c3c(c(O)c2C[C@H]1O)C(=O)C=C(N1CCCCC1)C3=O

Standard InChI:  InChI=1S/C20H23NO6/c1-20(27)9-11-10(7-14(20)23)17(24)15-13(22)8-12(19(26)16(15)18(11)25)21-5-3-2-4-6-21/h8,14,23-25,27H,2-7,9H2,1H3/t14-,20+/m1/s1

Standard InChI Key:  KMTYDHBIRMVXDG-VLIAUNLRSA-N

Molfile:  

 
     RDKit          2D

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   20.7682   -3.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7682   -4.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4735   -4.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4735   -2.8437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1788   -3.2564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1772   -4.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8814   -4.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8805   -2.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5853   -3.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5871   -4.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2903   -4.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9964   -4.0662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9947   -3.2506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2869   -2.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0593   -2.8499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4747   -5.2952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4735   -2.0265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8821   -5.2962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7020   -2.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7044   -4.4743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8786   -2.0328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7003   -3.6567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0600   -2.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3551   -1.6276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6462   -2.0347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6466   -2.8529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3560   -3.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
  1 15  1  0
  3 16  2  0
  4 17  2  0
  7 18  1  0
 13 19  1  0
 12 20  1  6
  8 21  1  0
 13 22  1  6
 15 23  1  0
 15 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4513475

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 373.41

Molecular Weight (Monoisotopic): 373.1525

AlogP: 1.06

#Rotatable Bonds: 1

Polar Surface Area: 118.30

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.68

CX Basic pKa: ┄

CX LogP: 1.97

CX LogD: 1.95

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.54

Np Likeness Score: 1.74

References

1. Klein-Júnior LC, Corrêa R, Vander Heyden Y, Cechinel Filho V..  (2019)  All that glitters is not gold: Panning cytotoxic natural products and derivatives with a fused tricyclic backbone by the estimation of their leadlikeness for cancer treatment.,  166  [PMID:30684866] [10.1016/j.ejmech.2019.01.028]

Source

Source(1):

• Scientific Literature