Aulosirazole C

ID: ALA5199921

PubChem CID: 168010330

Max Phase: Preclinical

Molecular Formula: C13H7NO6S

Molecular Weight: 305.27

Names and Identifiers

Canonical SMILES:  COc1nsc2c1C(=O)c1c(O)ccc(C(=O)O)c1C2=O

Standard InChI:  InChI=1S/C13H7NO6S/c1-20-12-8-9(16)7-5(15)3-2-4(13(18)19)6(7)10(17)11(8)21-14-12/h2-3,15H,1H3,(H,18,19)

Standard InChI Key:  NTXPGPUNJDYDFF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
   -2.3522    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9232   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088   -1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5056   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2903   -0.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5452   -1.6583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3522   -1.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7752   -0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2903    0.4612    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5056    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088    1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9232    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377    1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9232    1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3522    1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 12  9  2  0
 13 12  1  0
  8 14  2  0
 14 13  1  0
 14 15  1  0
 15 16  2  0
  5 17  2  0
 17 15  1  0
 18  1  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5199921

   ---

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: 305.27

Molecular Weight (Monoisotopic): 304.9994

AlogP: 1.33

#Rotatable Bonds: 2

Polar Surface Area: 113.79

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.13

CX Basic pKa: ┄

CX LogP: 2.46

CX LogD: -1.04

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.73

Np Likeness Score: 0.28

References

1. Davis LJ, Maldonado AC, Khin M, Krunic A, Burdette JE, Orjala J..  (2022)  Aulosirazoles B and C from the Cyanobacterium Nostoc sp. UIC 10771: Analogues of an Isothiazolonaphthoquinone Scaffold that Activate Nuclear Transcription Factor FOXO3a in Ovarian Cancer Cells.,  85  (3.0): [PMID:35100504] [10.1021/acs.jnatprod.1c01030]

Source

Source(1):

• Scientific Literature