2-((3S,5R)-3,5-Diethyl-5-pentyltetrahydrofuran-2-yl)-2-hydroxyacetic acid

ID: ALA3810293

PubChem CID: 127043555

Max Phase: Preclinical

Molecular Formula: C15H28O4

Molecular Weight: 272.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC[C@]1(CC)C[C@H](CC)[C@@H]([C@H](O)C(=O)O)O1

Standard InChI:  InChI=1S/C15H28O4/c1-4-7-8-9-15(6-3)10-11(5-2)13(19-15)12(16)14(17)18/h11-13,16H,4-10H2,1-3H3,(H,17,18)/t11-,12-,13-,15+/m0/s1

Standard InChI Key:  AMFPUNUKBPDKTB-PWNZVWSESA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
    0.7500   -1.0323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.2760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2135    0.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7500   -1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1233   -2.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3692   -2.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9800   -3.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4725   -4.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9609   -5.1634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2270   -0.8533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9331   -1.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    2.7742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4997    1.8540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6077    2.6566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9268    2.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8188    1.5160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1763    3.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9461   -0.2864    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0345    3.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  5 11  1  1
 11 12  1  0
  3 13  1  6
  2 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 16 18  2  0
  2 19  1  6
 13 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3810293

   ---

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: 272.39

Molecular Weight (Monoisotopic): 272.1988

AlogP: 2.98

#Rotatable Bonds: 8

Polar Surface Area: 66.76

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.18

CX Basic pKa: ┄

CX LogP: 3.48

CX LogD: 0.43

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.67

Np Likeness Score: 1.65

References

1. Jamison MT, Dalisay DS, Molinski TF..  (2016)  Peroxide Natural Products from Plakortis zyggompha and the Sponge Association Plakortis halichondrioides-Xestospongia deweerdtae: Antifungal Activity against Cryptococcus gattii.,  79  (3): [PMID:26859086] [10.1021/acs.jnatprod.5b00951]

Source

Source(1):

• Scientific Literature