Aguerin B

ID: ALA520721

Chembl Id: CHEMBL520721

Cas Number: 68370-45-6

PubChem CID: 155102

Max Phase: Preclinical

Molecular Formula: C19H22O5

Molecular Weight: 330.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C(C)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)C(=C)[C@@H]2[C@H]2OC(=O)C(=C)[C@@H]21

Standard InChI:  InChI=1S/C19H22O5/c1-8(2)18(21)23-14-6-9(3)12-7-13(20)10(4)15(12)17-16(14)11(5)19(22)24-17/h12-17,20H,1,3-7H2,2H3/t12-,13-,14-,15-,16+,17+/m0/s1

Standard InChI Key:  ZGDWDAMVZDRRQA-NQLMQOPMSA-N

Alternative Forms

1. Parent:

   

   ALA520721

   AGUERIN B

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: 330.38

Molecular Weight (Monoisotopic): 330.1467

AlogP: 2.09

#Rotatable Bonds: 2

Polar Surface Area: 72.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.33

CX LogD: 2.33

Aromatic Rings: 0

Heavy Atoms: 24

QED Weighted: 0.48

Np Likeness Score: 3.39

References

1. Bruno M, Rosselli S, Maggio A, Raccuglia RA, Bastow KF, Lee KH..  (2005)  Cytotoxic activity of some natural and synthetic guaianolides.,  68  (7): [PMID:16038545] [10.1021/np0500575]

2. Chicca A, Tebano M, Adinolfi B, Ertugrul K, Flamini G, Nieri P..  (2011)  Anti-proliferative activity of aguerin B and a new rare nor-guaianolide lactone isolated from the aerial parts of Centaurea deflexa.,  46  (7): [PMID:21458113] [10.1016/j.ejmech.2011.03.011]

3. Cis J, Nowak G, Kisiel W.  (2006)  Antifeedant properties and chemotaxonomic implications of sesquiterpene lactones and syringin from Rhaponticum pulchrum,  34  (12): [10.1016/j.bse.2006.05.019]

4. Usuki T, Sato M, Hara S, Yoshimoto Y, Kondo R, Zimmermann S, Kaiser M, Brun R, Hamburger M, Adams M..  (2014)  Antitrypanosomal structure-activity-relationship study of synthetic cynaropicrin derivatives.,  24  (3): [PMID:24433861] [10.1016/j.bmcl.2013.12.099]

Source

Source(1):

• Scientific Literature