7,7,8,9-tetramethyl-2-(((2S,3R,4R)-2,3,4,5-tetrahydroxypentyl)oxy)-6,7-dihydro-3H,5H-pyrido[1,2,3-de]quinoxalin-3-one

ID: ALA5207203

PubChem CID: 90469177

Max Phase: Preclinical

Molecular Formula: C20H28N2O6

Molecular Weight: 392.45

Names and Identifiers

Canonical SMILES:  Cc1cc2nc(OC[C@H](O)[C@H](O)[C@H](O)CO)c(=O)n3c2c(c1C)C(C)(C)CC3

Standard InChI:  InChI=1S/C20H28N2O6/c1-10-7-12-16-15(11(10)2)20(3,4)5-6-22(16)19(27)18(21-12)28-9-14(25)17(26)13(24)8-23/h7,13-14,17,23-26H,5-6,8-9H2,1-4H3/t13-,14+,17-/m1/s1

Standard InChI Key:  SQGXCGPAFICJCS-JKIFEVAISA-N

Molfile:  

 
     RDKit          2D

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   -0.7009    0.7695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -0.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4155   -0.4672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302   -0.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8448   -0.4947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593   -0.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5593    0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8448    1.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1302    0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8172   -1.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025   -1.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3880   -1.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6418   -1.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2294   -2.0338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0136   -0.4672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0136    1.1818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7282    0.7970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4429    1.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1575    0.7970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8445    1.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5867    0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2739    1.2367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8445    2.0338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1575   -0.0275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4154    2.0338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2739    1.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2739   -0.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  1 10  1  0
  5 10  2  0
  6 11  1  0
 11 12  1  0
 12 13  1  0
  4 13  1  0
 11 14  1  0
 11 15  1  0
  3 16  2  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  6
 20 25  1  1
 19 26  1  6
  8 27  1  0
  7 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5207203

   7,8,10,10-tetramethyl-3-[(2S,3R,4R)-2,3,4,5-tetrahydroxypentoxy]-1,4-diazatricyclo[7.3.1.05,13]trideca-3,5(13),6,8-tetraen-2-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 392.45

Molecular Weight (Monoisotopic): 392.1947

AlogP: 0.15

#Rotatable Bonds: 6

Polar Surface Area: 125.04

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.76

CX Basic pKa: ┄

CX LogP: 0.63

CX LogD: 0.63

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.55

Np Likeness Score: 0.50

References

1. Shingare RD, MacMillan JB, Reddy DS..  (2022)  Antibiotic natural product hunanamycin A: Lead identification towards anti-Salmonella agents.,  236  [PMID:35421661] [10.1016/j.ejmech.2022.114245]

Source

Source(1):

• Scientific Literature