Yatein
Basic information
- CAS
40456-50-6- Standard SMILES
COc1cc(C[C@H]2C(=O)OC[C@@H]2Cc2ccc3c(c2)OCO3)cc(OC)c1OC- InChIKey
GMLDZDDTZKXJLU-JKSUJKDBSA-N- Molecular formula
- C22H24O7
- Average molar mass
- 400.4 g/mol
- Monoisotopic mass
- 400.1522031
Overview
Dihydroanhydropodorhizol is a member of the class of butan-4-olides carrying 3,4,5-trimethoxybenzyl and (1,3-benzodioxol-5-yl)methyl substituents at positions 3 and 4 respectively. It has a role as a plant metabolite. It is a butan-4-olide, a lignan, a member of benzodioxoles and a member of methoxybenzenes.
Names & identifiers
- Preferred name
- Yatein
- IUPAC
- (3R,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
- English name
- (3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one
- Molecular formula
- C22H24O7
- Molecular weight
- 400.42
Names & synonyms
Yatein40456-50-6DihydroanhydropodorhizolCHEBI:4553DTXSID50193471(3R,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one(3R,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-((3,4,5-trimethoxyphenyl)methyl)oxolan-2-oneRefChem:195611DTXCID60115962(-)-yatein(-)-deoxypodorhizoneDeoxypodorhizone
Show more names
Yatei(?)-YateinYatapoxvirusYatein(+)-DeoxypodorhizonYatein/deoxypodorhizone(-)-trans-3-(3,4-Methylenedioxybenzyl)-2-(3,4,5-trimethoxybenzyl)butyrolactone(3R)-3α-(3,4,5-Trimethoxybenzyl)-4β-(1,3-benzodioxole-5-ylmethyl)tetrahydrofuran-2-one
CHEMBL471067(3R,4R)-4-[(2H-1,3-benzodioxol-5-yl)methyl]-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one(3R,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]tetrahydrofuran-2-one2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)dihydro-3-((3,4,5-trimethoxyphenyl)methyl)-, trans-(-)-(3~{R},4~{R})-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)dihydro-3-[(3,4,5-trimethoxyphenyl)methyl]-, (3R,4R)-AC1L9DHEDeoxypodorhizon
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 72.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 7
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 541
Physicochemical properties
- Boiling point
- 564.9 · 564.9±45.0 °C(Predicted)
- Density
- 1.266 · 1.266±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- Soluble in DMSO
- form
- A solid
- color
- Colorless to light yellow
- InChI
- 1S/C22H24O7/c1-24-19-9-14(10-20(25-2)21(19)26-3)7-16-15(11-27-22(16)23)6-13-4-5-17-18(8-13)29-12-28-17/h4-5,8-10,15-16H,6-7,11-12H2,1-3H3/t15-,16+/m0/s1
- InChIKey
- GMLDZDDTZKXJLU-JKSUJKDBSA-N
- SMILES
- O1C[C@@H]([C@H](C1=O)Cc4cc(c(c(c4)OC)OC)OC)Cc2cc3c(cc2)OCO3
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- WGK Germany
- 3 · WGK 3
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
DescriptionYatein is a lignan that has been found in C. formosana and has diverse biological activities. It inhibits the cytochrome P450 (CYP) isoform CYP3A4 (IC50 = 1 μM). Yatein inhibits herpes simplex virus 1 (HSV-1) replication in a plaque reduction assay (IC50 = 30.6 μM). It induces apoptosis and production of reactive oxygen species (ROS) in, and is cytotoxic to, A549 and CL1-5 non-small cell lung cancer (NSCLC) cells (IC50s = 3.5 and 1.9 μM, respectively). Yatein inhibits aggregation of rabbit platelets induced by platelet-activating factor (PAF), collagen, or arachidonic acid (Item Nos. 90010 | 90010.1 | 10006607) in a concentration-dependent manner.
UsesYatein is a lignan isolated from A. chilensis, with antiproliferative activity[1]. Yatein suppresses herpes simplex virus type 1 (HSV-1 ) replication by interruption the immediate-early gene expression[2].
Additional notes
DefinitionChEBI: A member of the class of butan-4-olides carrying 3,4,5-trimethoxybenzyl and (1,3-benzodioxol-5-yl)methyl substituents at positions 3 and 4 respectively.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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