(E)-1-(3-(3,7-Dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylbutan-1-one

ID: ALA3331100

Chembl Id: CHEMBL3331100

Cas Number: 72008-04-9

PubChem CID: 14282627

Max Phase: Preclinical

Molecular Formula: C21H30O4

Molecular Weight: 346.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(C)C(=O)c1c(O)cc(O)c(C/C=C(\C)CCC=C(C)C)c1O

Standard InChI:  InChI=1S/C21H30O4/c1-6-15(5)20(24)19-18(23)12-17(22)16(21(19)25)11-10-14(4)9-7-8-13(2)3/h8,10,12,15,22-23,25H,6-7,9,11H2,1-5H3/b14-10+

Standard InChI Key:  YMYBAWFGDGMZLY-GXDHUFHOSA-N

Alternative Forms

1. Parent:

   

   ALA3331100

   1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4,6-trihydroxy-phenyl]-2-methyl-butan-1-one

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: 346.47

Molecular Weight (Monoisotopic): 346.2144

AlogP: 5.27

#Rotatable Bonds: 8

Polar Surface Area: 77.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.78

CX Basic pKa: ┄

CX LogP: 7.00

CX LogD: 6.85

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.44

Np Likeness Score: 2.34

References

1. Sun Q, Schmidt S, Tremmel M, Heilmann J, König B..  (2014)  Synthesis of natural-like acylphloroglucinols with anti-proliferative, anti-oxidative and tube-formation inhibitory activity.,  85  [PMID:25128665] [10.1016/j.ejmech.2014.08.017]

2. Fobofou SA, Franke K, Sanna G, Porzel A, Bullita E, La Colla P, Wessjohann LA..  (2015)  Isolation and anticancer, anthelminthic, and antiviral (HIV) activity of acylphloroglucinols, and regioselective synthesis of empetrifranzinans from Hypericum roeperianum.,  23  (19): [PMID:26358281] [10.1016/j.bmc.2015.08.028]

3. Kishore N, Kumar P, Shanker K, Verma AK..  (2019)  Human disorders associated with inflammation and the evolving role of natural products to overcome.,  179  [PMID:31255927] [10.1016/j.ejmech.2019.06.034]

4. Fuentes RG, Pearce KC, Du Y, Rakotondrafara A, Valenciano AL, Cassera MB, Rasamison VE, Crawford TD, Kingston DGI..  (2019)  Phloroglucinols from the Roots of Garcinia dauphinensis and Their Antiproliferative and Antiplasmodial Activities.,  82  (3): [PMID:30354100] [10.1021/acs.jnatprod.8b00379]

Source

Source(1):

• Scientific Literature