2-Hexadecynoic acid

ID: ALA1269411

Chembl Id: CHEMBL1269411

Cas Number: 2834-02-8

PubChem CID: 22600366

Max Phase: Preclinical

Molecular Formula: C17H30O2

Molecular Weight: 266.42

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-Hexadecynoic Acid | heptadec-2-ynoic acid|2-Heptadecynoic acid|17PF5N58XE|2834-02-8|UNII-17PF5N58XE|CHEMBL1269411|SCHEMBL3022654|DTXSID60626785|BDBM50329257

Canonical SMILES:  CCCCCCCCCCCCCCC#CC(=O)O

Standard InChI:  InChI=1S/C17H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(18)19/h2-14H2,1H3,(H,18,19)

Standard InChI Key:  VHVMWCWIYITOLN-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1269411

   Heptadec-2-ynoic 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: 266.42

Molecular Weight (Monoisotopic): 266.2246

AlogP: 5.17

#Rotatable Bonds: 12

Polar Surface Area: 37.30

Molecular Species: ACID

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.41

CX Basic pKa:

CX LogP: 6.80

CX LogD: 3.40

Aromatic Rings: 0

Heavy Atoms: 19

QED Weighted: 0.39

Np Likeness Score: 0.79

References

1. Tasdemir D, Sanabria D, Lauinger IL, Tarun A, Herman R, Perozzo R, Zloh M, Kappe SH, Brun R, Carballeira NM..  (2010)  2-Hexadecynoic acid inhibits plasmodial FAS-II enzymes and arrests erythrocytic and liver stage Plasmodium infections.,  18  (21): [PMID:20855214] [10.1016/j.bmc.2010.08.055]

2. Carballeira NM, Cartagena M, Sanabria D, Tasdemir D, Prada CF, Reguera RM, Balaña-Fouce R..  (2012)  2-Alkynoic fatty acids inhibit topoisomerase IB from Leishmania donovani.,  22  (19): [PMID:22932312] [10.1016/j.bmcl.2012.08.019]

3. Carballeira NM, Bwalya AG, Itoe MA, Andricopulo AD, Cordero-Maldonado ML, Kaiser M, Mota MM, Crawford AD, Guido RV, Tasdemir D..  (2014)  2-Octadecynoic acid as a dual life stage inhibitor of Plasmodium infections and plasmodial FAS-II enzymes.,  24  (17): [PMID:25103602] [10.1016/j.bmcl.2014.07.050]

4. Sanabria-Ríos DJ, Rivera-Torres Y, Rosario J, Gutierrez R, Torres-García Y, Montano N, Ortíz-Soto G, Ríos-Olivares E, Rodríguez JW, Carballeira NM..  (2015)  Chemical conjugation of 2-hexadecynoic acid to C5-curcumin enhances its antibacterial activity against multi-drug resistant bacteria.,  25  (22): [PMID:26483137] [10.1016/j.bmcl.2015.10.022]

Source

Source(1):

• Scientific Literature