3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid

ID: ALA1231562

Cas Number: 86879-39-2

PubChem CID: 123979

Product Number: C335807, Order Now?

Max Phase: Preclinical

Molecular Formula: C12H16O5

Molecular Weight: 240.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1oc(CCC(=O)O)c(C(=O)O)c1C

Standard InChI:  InChI=1S/C12H16O5/c1-3-4-8-7(2)11(12(15)16)9(17-8)5-6-10(13)14/h3-6H2,1-2H3,(H,13,14)(H,15,16)

Standard InChI Key:  WMCQWXZMVIETAO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    0.6450    0.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3901   -0.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4349   -0.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9198   -0.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4296    1.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6899    0.7808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6921    3.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5843   -1.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    2.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224    1.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6921    2.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0692   -2.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5394   -1.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8750   -0.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6955   -0.5850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7336   -2.8460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8897   -2.0061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  5  1  0
  1 10  2  0
  2  3  2  0
 14  2  1  0
  3  4  1  0
  3  6  1  0
  4  8  1  0
 10  6  1  0
 11  7  1  0
 12  8  1  0
  9 10  1  0
  9 11  1  0
 12 16  2  0
 12 17  1  0
 14 13  2  0
 14 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1231562

   3-Carboxy-4-methyl-5-propyl-2-furanpropanoic acid

Molecule Features

Natural Product: Yes

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: 240.25

Molecular Weight (Monoisotopic): 240.0998

AlogP: 2.26

#Rotatable Bonds: 6

Polar Surface Area: 87.74

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.87

CX Basic pKa: ┄

CX LogP: 2.30

CX LogD: -3.52

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.80

Np Likeness Score: 0.54

References

1. Deguchi T, Kusuhara H, Takadate A, Endou H, Otagiri M, Sugiyama Y..  (2004)  Characterization of uremic toxin transport by organic anion transporters in the kidney.,  65  (1): [PMID:14675047] [10.1111/j.1523-1755.2004.00354.x]

2. Deguchi T, Ohtsuki S, Otagiri M, Takanaga H, Asaba H, Mori S, Terasaki T..  (2002)  Major role of organic anion transporter 3 in the transport of indoxyl sulfate in the kidney.,  61  (1): [PMID:11967025] [10.1046/j.1523-1755.2002.00318.x]

3. Sun H, Huang Y, Frassetto L, Benet LZ..  (2004)  Effects of uremic toxins on hepatic uptake and metabolism of erythromycin.,  32  (1): [PMID:15286055] [10.1124/dmd.104.000521]

4. Nagy E, Liu Y, Prentice KJ, Sloop KW, Sanders PE, Batchuluun B, Hammond CD, Wheeler MB, Durham TB..  (2017)  Synthesis and Characterization of Urofuranoic Acids: In Vivo Metabolism of 2-(2-Carboxyethyl)-4-methyl-5-propylfuran-3-carboxylic Acid (CMPF) and Effects on in Vitro Insulin Secretion.,  60  (5): [PMID:28171722] [10.1021/acs.jmedchem.6b01668]

Source

Source(2):

• Scientific Literature
• TP-search Transporter Database