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Cubebin

CAT: 0013-GTR19227828-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19227828-01Size:1 mg
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Description
Cubebin is a bioactive lignan employed in life science research. It serves as a valuable tool compound for investigating anti-inflammatory and analgesic mechanisms in both in vitro cellular assays and in vivo preclinical models.
CAS Number
18423-69-3
Smiles
C ([C@@H]1[C@@H] (CC=2C=C3C (=CC2) OCO3) [C@@H] (O) OC1) C=4C=C5C (=CC4) OCO5
Molecular Formula
C20H20O6
Molecular Weight
356.374
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

(2S,3R,4R)-3,4-Bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-2-furanol

(-)-cubebin is a lignan that consists of tetrahydrofuran-2-ol substituted by two 1,3-benzodioxol-5-ylmethyl groups at positions 3 and 4 respectively (the 2S,3R,4R stereoisomer). It is isolated from the leaves of Piper nigrum and exhibits analgesic, anti-inflammatory, antimicrobial and trypanocidal activities. It has a role as an antimicrobial agent, an analgesic, a trypanocidal drug, a histamine antagonist, an anti-inflammatory agent and a plant metabolite. It is a lignan, a secondary alcohol, a lactol, a member of benzodioxoles and a cyclic acetal.

CAS Number18423-69-3
PubChem CID117443
IUPAC Name(2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol
Molecular FormulaC20H20O6
Molecular Weight356.4
XLogP3.4
Topological Polar Surface Area66.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Heavy Atom Count26
Formal Charge0
Complexity487
SMILES
C1[C@@H]([C@H]([C@H](O1)O)CC2=CC3=C(C=C2)OCO3)CC4=CC5=C(C=C4)OCO5
InChI
InChI=1S/C20H20O6/c21-20-15(6-13-2-4-17-19(8-13)26-11-24-17)14(9-22-20)5-12-1-3-16-18(7-12)25-10-23-16/h1-4,7-8,14-15,20-21H,5-6,9-11H2/t14-,15+,20-/m0/s1
InChIKey
DIYWRNLYKJKHAM-MDOVXXIYSA-N
Chemical Structure
2D Structure
2D structure of (2S,3R,4R)-3,4-Bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-2-furanol
CAS: 18423-69-3
CID: 117443
Formula: C20H20O6
MW: 356.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight356.4
XLogP33.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count4
Exact Mass356.12598835
Monoisotopic Mass356.12598835
Topological Polar Surface Area66.4 Ų
Heavy Atom Count26
Formal Charge0
Complexity487
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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