(2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

• ChemBase ID: 72612
• Molecular Formular: C29H38O4
• Molecular Mass: 450.60962
• Monoisotopic Mass: 450.2770097
• SMILES: C1(=O)C(=C(C2=CC=C3[C@](C2=C1)(CC[C@@]1([C@@]3(CC[C@@]2([C@H]1C[C@](CC2)(C)C(=O)O)C)C)C)C)C)O
• Canonical SMILES: O=C1C=C2C(=CC=C3[C@@]2(C)CC[C@@]2([C@]3(C)CC[C@@]3([C@H]2C[C@@](C)(CC3)C(=O)O)C)C)C(=C1O)C
• InChI: InChI=1S/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1
• InChIKey: KQJSQWZMSAGSHN-JJWQIEBTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid
• IUPAC Traditional name: triterpene
• Synonyms: 3-Hydroxy-2-oxo-24-nor-D:A-friedooleana-1(10),3,5,7-tetraen-29-oic Acid; (9β,13α,14β,20α)-3-Hydroxy-9,13-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic Acid; Celastrol; 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid; Tripterin; Celastrol

Database IDs

• CAS Number: 34157-83-0
• MDL Number: MFCD03424073
• PubChem SID: 162037537
• PubChem CID: 122724

CALCULATED PROPERTIES

• Acid pKa: 4.7766385
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.5325603
• LogD (pH = 7.4): 2.754979
• Log P: 5.330474
• Molar Refractivity: 132.7461 cm^3
• Polarizability: 50.732735 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >10 mg/mL; H2O: insoluble; Methanol
• Apperance: Orange Red Solid; red solid
• Melting Point: 219-230°C

Safety Information

• Storage Condition: -20°C
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 2
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C29H38O4

DETAILS

Selleck Chemicals - S1290

Research Area: Immunology
Biological Activity:
Celastrol, a plant-derived triterpene, has anti-inflammatory and immunosuppressive activity. It suppresses LPS-induced cytokine release in macrophages and monocytes (IC50=40nM for IL-1β and IL-1α, 80nM for IL-6, 110nM for prostaglandin E2 and 210nM for IL-8 and TNF-α). [1]

Sigma Aldrich - C0869

Biochem/physiol Actions
Celastrol is a potent antioxidant, and anti-inflammatory agent. It is a novel HSP90 inhibitor (disrupts Hsp90/Cdc37 complex), that exhibits anticancer (anti-angiogenic - suppresses VEGFR expression); antioxidant (inhibits lipid peroxidation) and anti-inflammatory activity (suppresses iNOS and inflammatory cytokine production).

Toronto Research Chemicals - C249500

An antioxidant natural product which inhibits the growth of human glioma xenografts in nude mice through suppressing VEGFR expression. Used for clinical treatment for rheumatoid arthritis, was demonstrated to have antiangiogenic activity, and be inhibito

REFERENCES

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• Folkman, J., et al.: Nature, 1, 27 (1983)
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• Grosios, K., et al.: Inflamm. Res., 53, 133 (1983)
• Yang, H., et al.: Cancer Res., 66, 4758 (1983)