(3S)-((7S)-3-(hepta-1,3,5-trienyl)-7-methyl-6,8-dioxo-1a,6,7,8-tetrahydrooxireno[2,3-j]isochromen-7-yl)3-hydroxybutanoate

ID: ALA454065

PubChem CID: 9977422

Max Phase: Preclinical

Molecular Formula: C21H22O7

Molecular Weight: 386.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: CT-2108A | CT2108A|CHEBI:65678|CT-2108A|CHEMBL454065|(7S)-3-[(1E,3E,5E)-hepta-1,3,5-trien-1-yl]-7-methyl-6,8-dioxo-7,8-dihydro-6H-oxireno[j]isochromen-7-yl (3S)-3-hydroxybutanoate|BDBM50478476|Q27134161|[(7S)-3-[(1E,3E,5E)-hepta-1,3,5-trienyl]-7-methyl-6,8-dioxo-1aH-oxireno[2,3-j]isochromen-7-yl] (3S)-3-hydroxybutanoate

Canonical SMILES:  C/C=C/C=C/C=C/C1=CC2=CC(=O)[C@](C)(OC(=O)C[C@H](C)O)C(=O)C23OC3O1

Standard InChI:  InChI=1S/C21H22O7/c1-4-5-6-7-8-9-15-11-14-12-16(23)20(3,27-17(24)10-13(2)22)18(25)21(14)19(26-15)28-21/h4-9,11-13,19,22H,10H2,1-3H3/b5-4+,7-6+,9-8+/t13-,19?,20-,21?/m0/s1

Standard InChI Key:  DHOBWLDZMMCUPR-QBINLZOGSA-N

Molfile:  

     RDKit          2D

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   -1.2693    1.2401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557    0.8309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5557    2.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1577    2.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5827    1.2341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5863    2.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8714    2.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8644    0.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    1.2341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1566    0.4162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2964    2.4759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0104    2.0668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7244    2.4801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4384    2.0710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1524    2.4843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8663    2.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5803    2.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9864    2.4780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9874    1.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9874    0.8309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7010    1.2483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4194    0.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6963    2.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1329    1.2565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1282    2.0832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8512    0.8473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5579    0.0042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
  1  4  1  0
 13 14  1  0
  2  3  1  0
 14 15  2  0
  5  8  1  0
 15 16  1  0
  9  6  1  0
 16 17  2  0
  6  7  1  0
 17 18  1  0
  7  8  2  0
  1 19  2  0
 10  9  1  0
  2 20  1  6
 11 10  1  0
  2 21  1  0
  9 11  1  0
 21 22  1  0
  3 10  1  0
 22 23  1  0
  5  4  2  0
 22 24  2  0
  5 10  1  0
 23 25  1  0
 25 26  1  6
  7 12  1  0
 25 27  1  0
  1  2  1  0
  3 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA454065

   (7S)-3-[(1E,3E,5E)-hepta-1,3,5-trien-1-yl]-7-methyl-6,8-dioxo-7,8-dihydro-6H-oxireno[j]isochromen-7-yl (3S)-3-hydroxybutanoate

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: 386.40

Molecular Weight (Monoisotopic): 386.1366

AlogP: 1.84

#Rotatable Bonds: 6

Polar Surface Area: 102.43

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.59

CX LogD: 2.59

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.32

Np Likeness Score: 2.67

References

1. Laakso JA, Raulli R, McElhaney-Feser GE, Actor P, Underiner TL, Hotovec BJ, Mocek U, Cihlar RL, Broedel SE..  (2003)  CT2108A and B: New fatty acid synthase inhibitors as antifungal agents.,  66  (8): [PMID:12932120] [10.1021/np030046g]

Source

Source(1):

• Scientific Literature