Wedelolactone
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Wedelolactone
structure -
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CAS No:
524-12-9
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Formula:
C16H10O7
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Chemical Name:
Wedelolactone
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Synonyms:
6H-Benzofuro[3,2-c][1]benzopyran-6-one,1,8,9-trihydroxy-3-methoxy-;1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c][1]benzopyran-6-one;Wedelolactone;1,8,9-Trihydroxy-3-methoxy-[1]benzofuro[3,2-c]chromen-6-one
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CAS No:
Description
Wedelolactone, a natural product from Ecliptae herba, suppresses LPS-induced caspase-11 expression by directly inhibiting the IKK Complex[1]. Wedelolactone inhibits 5-lipoxygenase (5-Lox) (IC50~2.5 μM) activity by an oxygen radical scavenging mechanism. Wedelolactone induces caspase-dependent apoptosis in prostate cancer cells via downregulation of PKCε without inhibiting Akt[2]. Anti-cancer, anti-inflammatory, and antioxidant activities[3].
Wedelolactone is a member of the class of coumestans that is coumestan with hydroxy substituents as positions 1, 8 and 9 and a methoxy substituent at position 3. It has a role as an antineoplastic agent, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an apoptosis inducer, a hepatoprotective agent and a metabolite. It is a member of coumestans, a delta-lactone, an aromatic ether and a polyphenol. It derives from a coumestan.
Characteristics
109
2.4
brown-beige solid
1.7±0.1 g/cm3
327-329 °C (decomp)
498.4°C at 760 mmHg
255.2±28.7 °C
1.759
DMSO: 14 mg/mL, soluble
2-8°C
Safety Information
NONH for all modes of transport
3
22-43
36/37
Xn
P280-P301 + P312 + P330
H302-H317
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P272, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Wedelolactone Use and Manufacturing
Polyketides [PK] -> Flavonoids [PK12] -> Coumestan flavonoids [PK1209]
Computed Properties
Molecular Weight:314.25
XLogP3:2.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:1
Exact Mass:314.04265265
Monoisotopic Mass:314.04265265
Topological Polar Surface Area:109
Heavy Atom Count:23
Complexity:483
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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