trans-4-Isopropylidene-2-undecyl-5-oxo-tetrahydrofuran-3-carboxylic acid

ID: ALA517501

PubChem CID: 44582397

Max Phase: Preclinical

Molecular Formula: C19H32O4

Molecular Weight: 324.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCC[C@H]1OC(=O)C(=C(C)C)[C@@H]1C(=O)O

Standard InChI:  InChI=1S/C19H32O4/c1-4-5-6-7-8-9-10-11-12-13-15-17(18(20)21)16(14(2)3)19(22)23-15/h15,17H,4-13H2,1-3H3,(H,20,21)/t15-,17-/m1/s1

Standard InChI Key:  RESUZWQXMGIFHK-NVXWUHKLSA-N

Molfile:  

     RDKit          2D

 23 23  0  0  0  0  0  0  0  0999 V2000
    3.2863  -18.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0696  -19.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7595  -19.4897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4027  -18.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1101  -18.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1987  -19.1899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5622  -17.5120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3859  -17.5584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1906  -16.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7677  -17.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0665  -16.8277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9524  -17.7225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3532  -19.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6407  -19.0304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9242  -19.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2117  -19.0236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5047  -19.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2172  -19.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9336  -19.4259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461  -19.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3625  -19.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0750  -19.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7915  -19.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 10 12  2  0
  1 10  1  1
  4  6  2  0
  2 13  1  6
 13 14  1  0
  5  7  2  0
 14 15  1  0
  2  3  1  0
 15 16  1  0
  7  8  1  0
 16 17  1  0
  3  4  1  0
 17 18  1  0
  7  9  1  0
 18 19  1  0
  4  5  1  0
 19 20  1  0
  5  1  1  0
 20 21  1  0
  1  2  1  0
 21 22  1  0
 10 11  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA517501

   trans-4-Isopropylidene-2-undecyl-5-oxo-tetrahydrofuran-3-carboxylic acid

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: 324.46

Molecular Weight (Monoisotopic): 324.2301

AlogP: 4.87

#Rotatable Bonds: 11

Polar Surface Area: 63.60

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.37

CX Basic pKa: ┄

CX LogP: 5.78

CX LogD: 2.87

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.33

Np Likeness Score: 1.11

References

1. Wang X, Lin J, Chen Y, Zhong W, Zhao G, Liu H, Li S, Wang L, Li S..  (2009)  Novel fatty acid synthase (FAS) inhibitors: design, synthesis, biological evaluation, and molecular docking studies.,  17  (5): [PMID:19223187] [10.1016/j.bmc.2009.01.050]

Source

Source(1):

• Scientific Literature