(R)-5-(fluoromethyl)-3-((R)-13-hydroxy-13-((2R,5R)-5-((R)-1-hydroxytridecyl)tetrahydrofuran-2-yl)tridecyl)furan-2(5H)-one

ID: ALA1834283

PubChem CID: 56678764

Max Phase: Preclinical

Molecular Formula: C35H63FO5

Molecular Weight: 582.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCC[C@@H](O)[C@H]1CC[C@H]([C@H](O)CCCCCCCCCCCCC2=C[C@H](CF)OC2=O)O1

Standard InChI:  InChI=1S/C35H63FO5/c1-2-3-4-5-6-7-11-14-17-20-23-31(37)33-25-26-34(41-33)32(38)24-21-18-15-12-9-8-10-13-16-19-22-29-27-30(28-36)40-35(29)39/h27,30-34,37-38H,2-26,28H2,1H3/t30-,31-,32-,33-,34-/m1/s1

Standard InChI Key:  RHGSNTAYBMYTJF-SLXQPGMDSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA1834283

   (2R)-2-(fluoromethyl)-4-[(13R)-13-hydroxy-13-[(2R,5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-yl]tridecyl]-2H-furan-5-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: 582.88

Molecular Weight (Monoisotopic): 582.4660

AlogP: 9.07

#Rotatable Bonds: 27

Polar Surface Area: 75.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.62

CX Basic pKa: ┄

CX LogP: 10.32

CX LogD: 10.32

Aromatic Rings: ┄

Heavy Atoms: 41

QED Weighted: 0.07

Np Likeness Score: 1.38

References

1. Kojima N, Suga Y, Hayashi H, Yamori T, Yoshimitsu T, Tanaka T..  (2011)  Design and synthesis of C35-fluorinated solamins and their growth inhibitory activities against human cancer cell lines.,  21  (19): [PMID:21875800] [10.1016/j.bmcl.2011.08.011]

2. Kojima N, Abe M, Suga Y, Ohtsuki K, Tanaka T, Iwasaki H, Yamashita M, Miyoshi H..  (2013)  Critical role of a methyl group on the γ-lactone ring of annonaceous acetogenins in the potent inhibition of mitochondrial complex I.,  23  (5): [PMID:23375227] [10.1016/j.bmcl.2013.01.018]

Source

Source(1):

• Scientific Literature