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Chebulinic acid

CAT: 0804-HY-N2033-02Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N2033-02Size:5 mg
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Description
Chebulinic acid is a potent natural inhibitor of M. tuberculosis DNA gyrase, also can inhibit SMAD-3 phosphorylation, inhibit H+ K+-ATPase activity.
CAS Number
18942-26-2
UNSPSC
12352005
Hazard Statement
H315, H319
Target
DNA/RNA Synthesis; Proton Pump; TGF-beta/Smad
Type
Natural Products
Related Pathways
Cell Cycle/DNA Damage; Membrane Transporter/Ion Channel; Stem Cell/Wnt; TGF-beta/Smad
Applications
Neuroscience-Neuromodulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/Chebulinic-acid.html
Purity
99.68
Solubility
DMSO : 100 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
OC(C[C@H](C(O[C@@]([C@H](O[C@H]1OC(C2=CC(O)=C(O)C(O)=C2)=O)COC(C3=CC(O)=C(O)C(O)=C3)=O)([H])[C@@](OC(C4=CC(O)=C(O)C(O)=C4)=O)([H])[C@@]1([H])OC5=O)=O)[C@@]([C@H]6O)([H])C(C5=CC(O)=C7O)=C7OC6=O)=O
Molecular Formula
C41H32O27
Molecular Weight
956.68
Precautions
H315, H319
References & Citations
[1]Patel K et al. Identification of chebulinic acid as potent natural inhibitor of M. tuberculosis DNA gyrase and molecular insights into its binding mode of action. Comput Biol Chem. 2015 Dec;59 Pt A:37-47.|[2]Sivasankar S et al. Aqueous and alcoholic extracts of Triphala and their active compounds chebulagic acid and chebulinic acidprevented epithelial to mesenchymal transition in retinal pigment epithelial cells, by inhibiting SMAD-3 phosphorylation. PLoS One. 2015 Mar 20|[3]Mishra V et al. Anti-secretory and cyto-protective effects of chebulinic acid isolated from the fruits of Terminalia chebula on gastric ulcers. Phytomedicine. 2013 Apr 15;20 (6) :506-11.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Chebulinic Acid

chebulinic acid has been reported in Terminalia, Terminalia chebula, and Lumnitzera racemosa with data available.

CAS Number18942-26-2
PubChem CID99937814
IUPAC Name2-[(4R,5S,7R,8R,11S,12S,13R,21S)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis[(3,4,5-trihydroxybenzoyl)oxy]-7-[(3,4,5-trihydroxybenzoyl)oxymethyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.14,8.016,20]henicosa-1(19),16(20),17-trien-11-yl]acetic acid
Molecular FormulaC41H32O27
Molecular Weight956.7
XLogP0.7
Topological Polar Surface Area447
Hydrogen Bond Donor Count13
Hydrogen Bond Acceptor Count27
Rotatable Bond Count12
Heavy Atom Count68
Formal Charge0
Complexity1880
SMILES
C1=C(C=C(C(=C1O)O)O)C(=O)OC[C@@H]2[C@@H]3[C@@H]([C@H]([C@@H](O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C6=C5[C@H]([C@@H](C(=O)O3)CC(=O)O)[C@H](C(=O)O6)O)O)O)OC(=O)C7=CC(=C(C(=C7)O)O)O
InChI
InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22+,24-,30+,31+,33-,34+,41-/m0/s1
InChIKey
YGVHOSGNOYKRIH-AVXZFDTDSA-N
Chemical Structure
2D Structure
2D structure of Chebulinic Acid
CAS: 18942-26-2
CID: 99937814
Formula: C41H32O27
MW: 956.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight956.7
XLogP30.7
Hydrogen Bond Donor Count13
Hydrogen Bond Acceptor Count27
Rotatable Bond Count12
Exact Mass956.11309574
Monoisotopic Mass956.11309574
Topological Polar Surface Area447 Ų
Heavy Atom Count68
Formal Charge0
Complexity1880
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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