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Caffeoylcalleryanin

CAT: 0804-HY-N12987Size: 1 EachDry Ice: NoHazardous: No
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CAT#:0804-HY-N12987Size:1 Each
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Description
Caffeoylcalleryanin is a potent 15-lipoxygenase inhibitor with an IC50 value of 1.59 µM. Caffeoylcalleryanin shows no cytotoxic[1].
CAS Number
20300-49-6
UNSPSC
12352005
Target
Lipoxygenase
Type
Natural Products
Related Pathways
Metabolic Enzyme/Protease
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Others
Assay Protocol
https://www.medchemexpress.com/caffeoylcalleryanin.html
Smiles
OC[C@H]([C@H]([C@@H]([C@H]1O)O)O)O[C@H]1OC2=C(C=C(C=C2)COC(/C=C/C3=CC(O)=C(C=C3)O)=O)O
Molecular Formula
C22H24O11
Molecular Weight
464.42
References & Citations
[1]Alvarenga TA, et al. Lipoxygenase inhibitory activity of Cuspidaria pulchra and isolated compounds. Nat Prod Res. 2015;29 (11) :1083-6.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported
Isoform
15-LOX

Chemical Information

Caffeoylcalleryanin

[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate has been reported in Strychnos axillaris with data available.

CAS Number20300-49-6
PubChem CID73669456
IUPAC Name[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Molecular FormulaC22H24O11
Molecular Weight464.4
XLogP0.5
Topological Polar Surface Area186
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count11
Rotatable Bond Count8
Heavy Atom Count33
Formal Charge0
Complexity658
SMILES
C1=CC(=C(C=C1COC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
InChI
InChI=1S/C22H24O11/c23-9-17-19(28)20(29)21(30)22(33-17)32-16-5-2-12(8-15(16)26)10-31-18(27)6-3-11-1-4-13(24)14(25)7-11/h1-8,17,19-26,28-30H,9-10H2/b6-3+/t17-,19-,20+,21-,22-/m1/s1
InChIKey
VTHLSAOVZTYBRV-FPULVWICSA-N
Chemical Structure
2D Structure
2D structure of Caffeoylcalleryanin
CAS: 20300-49-6
CID: 73669456
Formula: C22H24O11
MW: 464.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight464.4
XLogP30.5
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count11
Rotatable Bond Count8
Exact Mass464.13186158
Monoisotopic Mass464.13186158
Topological Polar Surface Area186 Ų
Heavy Atom Count33
Formal Charge0
Complexity658
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
M32504-01Caffeoylcalleryanin

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