SACRAMENTO — One of California’s more profitable card rooms agreed Thursday to a record $5.3 million penalty for misleading gambling regulators and violating a federal law designed to deter money laundering, the state attorney general’s office said.

Artichoke Joe’s Casino in San Bruno, south of San Francisco, failed to properly report an investigation by the federal Financial Crimes Enforcement Network, leading to the largest agreed-upon penalty in the history of California gambling regulation.

The state penalty is in addition to a $5 million federal settlement for failing to have an effective anti-money laundering program and failing to report certain suspicious activity between 2009 and 2017, state officials said. That $5 million is also the largest amount assessed against a California card room by federal regulators.

The general manager and human resources director at the 51-table cardroom did not return telephone messages Thursday nor direct requests for comment to others. The card room has California’s eighth-largest gross gambling revenue.

A decade ago, state gambling regulators accused the card room of engaging in loan-sharking activities, illegal drug sales, and failing to properly report violations, according to the most recent allegations. As part of that settlement, the card room did not contest the illegal loans allegation and the state dropped its claims of illegal drug sales and the reporting failure.

A federal criminal investigation at the time led to a 2011 racketeering indictment and conviction of two casino customers and others for loan-sharking and other illegal activities at the casino “with the direct assistance of the card club’s employees,” according to federal regulators.

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