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Ent-Rhizocarpic acid

CAT: 0804-HY-177540Size: 1 EachDry Ice: NoHazardous: No
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Description
Ent-Rhizocarpic acid is an enantiomer of Rhizocarpic acid. ent-Rhizocarpic acid has more potent antibacterial and antiparasitic activity against Staphylococcus aureus (ATCC 25923) and Giardiaduodenalis 713 compared to Rhizocarpic acid. ent-Rhizocarpic acid also has a weak but selective antitumor activity against NS-1 cells[1].
CAS Number
3061155-24-3
UNSPSC
12352005
Target
Bacterial; Drug Isomer; Parasite
Related Pathways
Anti-infection; Others
Field of Research
Cancer; Infection
Smiles
O=C(O/1)C(C2=CC=CC=C2)=C(O)C1=C(C(N[C@H](CC3=CC=CC=C3)C(OC)=O)=O)\C4=CC=CC=C4
Molecular Formula
C28H23NO6
Molecular Weight
469.49
References & Citations
[1]James PJC, et al. Synthesis, Characterization, and Bioactivity of the Lichen Pigments Pulvinamide, Rhizocarpic Acid, and Epanorin and Congeners. J Nat Prod. 2023 Mar 24;86 (3) :550-556.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

methyl (2R)-2-[[(2E)-2-(3-hydroxy-5-oxo-4-phenylfuran-2-ylidene)-2-phenylacetyl]amino]-3-phenylpropanoate
CAS Number3061155-24-3
PubChem CID171355092
IUPAC Namemethyl (2R)-2-[[(2E)-2-(3-hydroxy-5-oxo-4-phenylfuran-2-ylidene)-2-phenylacetyl]amino]-3-phenylpropanoate
Molecular FormulaC28H23NO6
Molecular Weight469.5
XLogP4.3
Topological Polar Surface Area102
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count8
Heavy Atom Count35
Formal Charge0
Complexity857
SMILES
COC(=O)[C@@H](CC1=CC=CC=C1)NC(=O)/C(=C/2\C(=C(C(=O)O2)C3=CC=CC=C3)O)/C4=CC=CC=C4
InChI
InChI=1S/C28H23NO6/c1-34-27(32)21(17-18-11-5-2-6-12-18)29-26(31)23(20-15-9-4-10-16-20)25-24(30)22(28(33)35-25)19-13-7-3-8-14-19/h2-16,21,30H,17H2,1H3,(H,29,31)/b25-23+/t21-/m1/s1
InChIKey
DKDGWAKCXBFTMM-CQGYNDIISA-N
Chemical Structure
2D Structure
2D structure of methyl (2R)-2-[[(2E)-2-(3-hydroxy-5-oxo-4-phenylfuran-2-ylidene)-2-phenylacetyl]amino]-3-phenylpropanoate
CAS: 3061155-24-3
CID: 171355092
Formula: C28H23NO6
MW: 469.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight469.5
XLogP34.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count8
Exact Mass469.15253745
Monoisotopic Mass469.15253745
Topological Polar Surface Area102 Ų
Heavy Atom Count35
Formal Charge0
Complexity857
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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