structure of Rotundifuran

Rotundifuran

CAS No.: 50656-65-0
M. Wt: 362.50300
M. Fa: C22H34O4
InChI Key: QKHCQFQIJKXMOE-UGFIEOPBSA-N
Appearance: White to Off-White Solid

Names and Identifiers of Rotundifuran

CAS Number

50656-65-0

IUPAC Name

[(1R,3R,4R,4aS,8aS)-4-[2-(furan-3-yl)ethyl]-4-hydroxy-3,4a,8,8-tetramethyl-2,3,5,6,7,8a-hexahydro-1H-naphthalen-1-yl] acetate

InChI

InChI=1S/C22H34O4/c1-15-13-18(26-16(2)23)19-20(3,4)9-6-10-21(19,5)22(15,24)11-7-17-8-12-25-14-17/h8,12,14-15,18-19,24H,6-7,9-11,13H2,1-5H3/t15-,18-,19+,21+,22-/m1/s1

InChIKey

QKHCQFQIJKXMOE-UGFIEOPBSA-N

Canonical SMILES

CC1CC(C2C(CCCC2(C1(CCC3=COC=C3)O)C)(C)C)OC(=O)C

Isomeric SMILES

C[C@@H]1C[C@H]([C@@H]2[C@@]([C@]1(CCC3=COC=C3)O)(CCCC2(C)C)C)OC(=O)C

UNII

T2UY9AYG4O

Physical and chemical properties of Rotundifuran

Acidity coefficient

14.66±0.70(Predicted)

Boiling Point

432.9±35.0 °C(Predicted)

Density

1.09±0.1 g/cm3(Predicted)

Exact Mass

362.24600

LogP

4.74740

Molecular Formula

C22H34O4

Molecular Weight

362.50300

PSA

59.67000

Storage condition

2-8℃

Applications of Rotundifuran

Rotundifuran has several applications:

  • Pharmaceuticals: Its potential as an anticancer agent makes it valuable in developing cancer therapies.
  • Anti-inflammatory Treatments: Due to its ability to modulate inflammatory pathways, it may be used in treating inflammatory diseases.
  • Nutraceuticals: Its natural origin allows for incorporation into dietary supplements aimed at enhancing health.

Interaction Studies of Rotundifuran

Studies have explored Rotundifuran's interactions with various biological targets. Notably, it has been identified as a potential target for the Cyr61 protein, which plays a role in cancer progression. Furthermore, it has been shown to sensitize cancer cells to ferroptosis by modulating iron metabolism and reactive oxygen species levels.

Biological Activity of Rotundifuran

Rotundifuran exhibits significant biological activities, particularly in cancer treatment. Research indicates that it induces ferroptotic cell death in lung cancer cells, inhibiting cell growth and promoting apoptosis through various pathways, including the NF-κB and MAPK pathways. Additionally, it has shown potential anti-inflammatory effects by suppressing inflammatory mediators in immune cells.