(S)-((S)-3-(hepta-1,3,5-trienyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl)3-hydroxybutanoate

ID: ALA454066

PubChem CID: 10044646

Max Phase: Preclinical

Molecular Formula: C21H22O6

Molecular Weight: 370.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: CT-2108B | CT2108B|CHEBI:65679|CT-2108B|CHEMBL454066|(7S)-3-[(1E,3E,5E)-hepta-1,3,5-trien-1-yl]-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl (3S)-3-hydroxybutanoate|BDBM50478477|Q27134162|[(7S)-3-[(1E,3E,5E)-Hepta-1,3,5-trienyl]-7-methyl-6,8-dioxoisochromen-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)C2=CO1

Standard InChI:  InChI=1S/C21H22O6/c1-4-5-6-7-8-9-16-11-15-12-18(23)21(3,20(25)17(15)13-26-16)27-19(24)10-14(2)22/h4-9,11-14,22H,10H2,1-3H3/b5-4+,7-6+,9-8+/t14-,21-/m0/s1

Standard InChI Key:  DWEOLLYPKQIHIN-JOAINMFFSA-N

Molfile:  

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   10.7025    1.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4155    0.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4155    2.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1285    1.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5526    1.1414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5562    1.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8419    2.3860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8348    0.7336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1264    1.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2659    2.3825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9794    1.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6929    2.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4064    1.9778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1199    2.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8334    1.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9858    2.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9848    1.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9848    0.7385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2717    1.1557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5539    0.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2764    1.9819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8408    1.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8455    1.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1230    0.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4134   -0.0876    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  7  8  2  0
  2 19  1  6
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  2 20  1  0
  3 10  1  0
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  5  4  2  0
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  7 11  1  0
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 24 25  1  6
 11 12  2  0
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  3 27  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA454066

   (7S)-3-[(1E,3E,5E)-hepta-1,3,5-trien-1-yl]-7-methyl-6,8-dioxo-7,8-dihydro-6H-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: 370.40

Molecular Weight (Monoisotopic): 370.1416

AlogP: 2.62

#Rotatable Bonds: 6

Polar Surface Area: 89.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.46

CX LogD: 2.46

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.44

Np Likeness Score: 2.82

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