NA

ID: ALA4207229

PubChem CID: 11026625

Max Phase: Preclinical

Molecular Formula: C17H17NO11S

Molecular Weight: 443.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)O[C@@H]2[C@H]3OS(=O)(=O)O[C@H]3[C@]3(O)c4cc5c(c(O)c4C(=O)N[C@H]3[C@@H]2O1)OCO5

Standard InChI:  InChI=1S/C17H17NO11S/c1-16(2)26-10-11(27-16)13-17(21,14-12(10)28-30(22,23)29-14)5-3-6-9(25-4-24-6)8(19)7(5)15(20)18-13/h3,10-14,19,21H,4H2,1-2H3,(H,18,20)/t10-,11+,12+,13-,14+,17-/m0/s1

Standard InChI Key:  GOXGCXIPDLVQKN-UFZBQXAWSA-N

Molfile:  

     RDKit          2D

 35 40  0  0  0  0  0  0  0  0999 V2000
   15.2542  -10.7143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5444  -11.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2588  -11.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8381   -8.9643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5521   -9.3771    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.5510   -8.5539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8369  -11.5067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1270  -12.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8369  -13.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5468  -11.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1270  -11.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5468  -12.7449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4171  -13.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7155  -12.7449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7155  -11.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4171  -11.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9313  -12.9884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9313  -11.6677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8369  -13.9707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4484  -12.3280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4171  -13.9707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5468  -11.1105    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1889  -11.1683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8410  -10.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5568  -10.2729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3777   -9.4633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2195  -10.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2777  -10.6896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2608  -11.5191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0445  -11.7957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0719  -10.4536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1328   -9.6866    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9991  -10.7638    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2567  -12.3404    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4919   -9.8930    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  2  0
  6  5  2  0
  8 11  1  0
  9  8  1  0
 10  7  1  0
 11  7  1  0
 12 10  1  0
 13  8  2  0
 24  7  1  0
 29 10  1  0
 14 15  2  0
 28 25  1  0
 15 16  1  0
 16 11  2  0
 17 14  1  0
 18 15  1  0
 19  9  2  0
 20 18  1  0
 21 13  1  0
 10 22  1  1
  9 12  1  0
 14 13  1  0
 17 20  1  0
  7 23  1  6
 24 25  1  0
 25 26  1  0
 26  5  1  0
  5 27  1  0
 27 24  1  0
 28 29  1  0
 29 30  1  0
 30  2  1  0
  2 31  1  0
 31 28  1  0
 25 32  1  1
 24 33  1  1
 29 34  1  6
 28 35  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4207229

   (1S,13S,14S,18S,19R,23R)-1,9-dihydroxy-16,16-dimethyl-21,21-dioxo-5,7,15,17,20,22-hexaoxa-21lambda6-thia-12-azahexacyclo[11.10.0.02,10.04,8.014,18.019,23]tricosa-2,4(8),9-trien-11-one

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: 443.39

Molecular Weight (Monoisotopic): 443.0522

AlogP: -1.02

#Rotatable Bonds: ┄

Polar Surface Area: 159.08

Molecular Species: NEUTRAL

HBA: 11

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.39

CX Basic pKa: ┄

CX LogP: 0.08

CX LogD: 0.04

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.45

Np Likeness Score: 1.34

References

1. Nair JJ, Wilhelm A, Bonnet SL, van Staden J..  (2017)  Antibacterial constituents of the plant family Amaryllidaceae.,  27  (22): [PMID:29033234] [10.1016/j.bmcl.2017.09.052]

Source

Source(1):

• Scientific Literature