(R)-1-[(2R,5R,2'R,5'R)-5'-((R)-1-hydroxy-undecyl)-octahydro-[2,2']bifuranyl-5-yl]-undecan-1-ol

ID: ALA464549

Chembl Id: CHEMBL464549

PubChem CID: 10457969

Max Phase: Preclinical

Molecular Formula: C30H58O4

Molecular Weight: 482.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCC[C@@H](O)[C@H]1CC[C@H]([C@H]2CC[C@H]([C@H](O)CCCCCCCCCC)O2)O1

Standard InChI:  InChI=1S/C30H58O4/c1-3-5-7-9-11-13-15-17-19-25(31)27-21-23-29(33-27)30-24-22-28(34-30)26(32)20-18-16-14-12-10-8-6-4-2/h25-32H,3-24H2,1-2H3/t25-,26-,27-,28-,29-,30-/m1/s1

Standard InChI Key:  AUCMVFPGZUARCL-VHNXJUCRSA-N

Alternative Forms

1. Parent:

   

   ALA464549

   dleta-lac-Acetogenin

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: 482.79

Molecular Weight (Monoisotopic): 482.4335

AlogP: 7.87

#Rotatable Bonds: 21

Polar Surface Area: 58.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.90

CX Basic pKa: ┄

CX LogP: 8.74

CX LogD: 8.74

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.16

Np Likeness Score: 1.13

References

1. Ichimaru N, Abe M, Murai M, Senoh M, Nishioka T, Miyoshi H..  (2006)  Function of the alkyl side chains of Deltalac-acetogenins in the inhibitory effect on mitochondrial complex I (NADH-ubiquinone oxidoreductase).,  16  (13): [PMID:16621539] [10.1016/j.bmcl.2006.03.082]

2. Chapuis JC, Khdour O, Cai X, Lu J, Hecht SM..  (2009)  Synthesis and characterization of Deltalac-acetogenins that potently inhibit mitochondrial complex I.,  17  (6): [PMID:19027304] [10.1016/j.bmc.2008.10.071]

3. Murai M, Ichimaru N, Abe M, Nishioka T, Miyoshi H.  (2006)  Synthesis of photolabile lac-acetogenin for photoaffinity labeling of mitochondrial complex I,  31  (2): [10.1584/jpestics.31.156]

Source

Source(1):

• Scientific Literature